Title: Holiday Rentals Winchester from £191: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

 

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# Search Holiday Rentals in Winchester

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## Check prices for these dates

Tonight

[25 Nov - 26 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-25&endDate=2025-11-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[26 Nov - 27 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-26&endDate=2025-11-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Holiday Rentals in Winchester

![Living area](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1117h810x5y0-b88c2c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/288bbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1025h1046x4y3-ad71c285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1248h1670x0y0-152d5b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Morocco Loft 2BR overlooking city walking mall

Old Town Winchester

10/10

Exceptional

(2)

"Great property with all the comforts of home"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristen R.

£251

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Winchester-Hotels-Morocco-Loft-2BR-Overlooking-City-Walking-Mall.h107895789.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/9a2bb6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/4c56e3e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/59a5c7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

Front Royal

10/10

Exceptional

(2)

"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jay L.

£313

includes taxes & fees

2 Dec - 3 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/8d41db14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vue - Mountain top hot tub overlooking the Shenandoah River

Front Royal

9.8/10

Exceptional

(10)

"Love the view and beautiful appointed decor throughout the home…"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lynn M.

£317

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112790000/112787100/112787004/5a1906cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112790000/112787100/112787004/c79ce850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112790000/112787100/112787004/2ceb8070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112790000/112787100/112787004/0626156b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wilderness Ridge | Private Cabin w/ Mountain Views

Linden

9.4/10

Exceptional

(6)

"great get away for a family retreat!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rex P.

£376

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Linden-Hotels-Wilderness-Ridge-Private-Cabin-W-Mountain-Views.h112787004.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/17745535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/0bb76882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/dd32954f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/9b7a2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Honeymoon Cabin | Private Retreat w/ hot tub

Front Royal

10/10

Exceptional

(2)

"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul B.

£295

includes taxes & fees

8 Dec - 9 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Honeymoon-Cabin-Private-Retreat-W-Hot-Tub.h113027243.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568610/13b2ac5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568610/00a4b380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568610/680d6ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568610/2832ffaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Foundry Cabin | Historic 6BR Retreat w/ Hot Tub, Propane Fire Pit & Games

Front Royal

9.8/10

Exceptional

(11)

"Comfortable and nice layout for group of nine friends during extended wine tasting weekend. The kitchen was wonderfully stocked as we do most of our cooking on these types of outings. Communication with owner was timely and responsive. Even the wildlife (deer, woodchuck, bunnies, etc.) were fun to watch as we relaxed on the back porch. All-in-all, a fantastic place to stay in a beautiful part of Virginia. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tom B.

£432

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Foundry-Cabin-Historic-6BR-Retreat-W-Hot-Tub.h87568610.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/w1350h899x0y1-efab187c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/c037b288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/f35a6e70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/aa8bac15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Far View Retreat | Private Cabin w/ Hot Tub, Screened Porch, Games, & More

Front Royal

10/10

Exceptional

(14)

"The cabin is very clean and well equipped. Matt is a great host. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tracy B.

£320

includes taxes & fees

8 Dec - 9 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-Far-View-Cabin-Private-Retreat-W-Hot-Tub.h93522518.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/88fd6b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/25a34129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/6278c5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/c54a2943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Linden

10/10

Exceptional

(1)

"This place was very nice and well equipped with everything that you would need. It was very clean, quiet and had plenty of space. This is a great place to stay if you're in the area. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael C.

£426

includes taxes & fees

7 Dec - 8 Dec

[](https://www.expedia.co.uk/Linden-Hotels-Cozy-Luxury.h118355581.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/4bba56d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/ce787f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/54b6b907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/3bbb4cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

Front Royal

10/10

Exceptional

(4)

"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

grace g.

£396

includes taxes & fees

15 Dec - 16 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Cozy-Bear-Cabin-Hot-Tub.h112549200.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/d3302e05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/234bd7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/23f4000c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury tiny home farm stay on historic property with hot tub in Stephens City

Stephens City

£128

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x1y1-de179e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2998h2002x1y1-e4dac9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x0y1-34023d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w3000h2002x0y1-874ebd45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcome to the Ladybug Retreat!

Boyce

10/10

Exceptional

(1)

"This home is lovely and the host has thought of everything. We will definitely stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Catherine A.

£315

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/2ca3d794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/7b940b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/20a8dae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/70f721a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More

Linden

9.8/10

Exceptional

(10)

"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bill A.

£309

includes taxes & fees

3 Dec - 4 Dec

[](https://www.expedia.co.uk/Linden-Hotels-Delicious-Cabin-Hot-Tub.h87551282.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104090000/104081500/104081491/8e13c176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104090000/104081500/104081491/1a4f7915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104090000/104081500/104081491/55c45b5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104090000/104081500/104081491/1e97a727.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Trillium Cabin | Modern Log Retreat with Hot Tub, Game Room & Mountain Views

Linden

9.6/10

Exceptional

(5)

"Enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly H.

£407

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Trillium-Cabin-Modern-Log-Retreat-With-Hot-Tub.h104081491.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/4516f505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/642d5e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/8d487597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/0f5f7b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Farm Suite at Valley View Farm

Delaplane

£233

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Farm-Suite-At-Valley-View-Farm.h121935788.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/2736c2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/7a491c77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/dda7ab71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, stovetop](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/93b157cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Riverfront Home Getaway with Hot Tub

Warren County

£371

includes taxes & fees

8 Dec - 9 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/e75c3693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/d9d55f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/w1284h952x0y7-6504b025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/bc11097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy English Basement Apt quiet but close to downtown

Winchester

9.6/10

Exceptional

(7)

"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

£137

includes taxes & fees

24 Dec - 25 Dec

[](https://www.expedia.co.uk/Winchester-Hotels-Cozy-English-Basement-Apt-Quiet-But-Close-To-Downtown.h75832325.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/a64ea9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/a66b4f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/8a63417e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/b436db87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Foxwood Cabin: Cozy Retreat w/ Hot Tub, Screened Porch, Firepit & Grill

Front Royal

10/10

Exceptional

(5)

"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alex H.

£311

includes taxes & fees

1 Dec - 2 Dec

[](https://www.expedia.co.uk/Front-Royal-Hotels-The-Foxwood-Cabin-Hot-Tub.h113303853.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/b3502d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/facc3b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e0ae9bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Scarborough Fair walk to downtown two story apt

Old Town Winchester

9.6/10

Exceptional

(5)

"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie L.

£305

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/80b59f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/cf8e60e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1413h1055x0y0-6561893b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

Old Town Winchester

9.0/10

Wonderful

(6)

"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tricia M.

£274

includes taxes & fees

30 Nov - 1 Dec

[](https://www.expedia.co.uk/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/a4ec224c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/1ca53946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/396388c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/6b5ccc9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cameron Charmer pristine downtown apt with double master suites

Winchester

9.4/10

Exceptional

(6)

"Nice house in a good central location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mitchell V.

£272

includes taxes & fees

7 Dec - 8 Dec

[](https://www.expedia.co.uk/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11&regionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Save up to 40% on select hotels.

[Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_BF_PROMO_6056879)

## Find holiday rentals that suit your style

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CABIN)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=COTTAGE)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VILLA)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CONDO)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CHALET)

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Save an average of 15% on thousands of hotels when you're signed in

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## Top Winchester Hotel Reviews

![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg)

### Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Friendly staff, on site bar/restaurant and clean, comfortable room."

[](https://expedia.co.uk/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg)

### TRU By Hilton Winchester

10/10 Excellent

"The entire hotel was clean, smelled great, and have everything you need. We have a fantastic stay."

[](https://expedia.co.uk/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg)

### Comfort Inn & Suites Winchester

10/10 Excellent

"The staff was courteous, and the room was spotless. The location was perfect for us."

[](https://expedia.co.uk/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

![Spark by Hilton Winchester](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg)

### Spark by Hilton Winchester

10/10 Excellent

"Exceptionally comfortable beds at this location! Courteous staff - quick and efficient check in/out process."

[](https://expedia.co.uk/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information)

![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg)

### Quality Inn Winchester

10/10 Excellent

"My wife and I are traveling with our dog and this hotel was very convenient off Rt81. Reasonable rates and pet friendly."

[](https://expedia.co.uk/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg)

### Travelodge by Wyndham Winchester

10/10 Excellent

"Clean and comfortable."

[](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg)

### SpringHill Suites by Marriott Winchester

10/10 Excellent

"Room style was very comfortable"

[](https://expedia.co.uk/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg)

### Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Nice clean pet friendly hotel not far from interstate 81"

[](https://expedia.co.uk/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"The breakfast was very good. The menu had a lot of options. It came to our table nice and hot! I loved the waffle with Lemon ricotta, syrup and butter. Our waitress always knew when to fill my coffee to keep it warm! Everything was very clean and neatly set up. The waitresses were also cheerful and friendly!"

[](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about** **Winchester** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winchester holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £191 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Winchester rentals**

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.co.uk
-   All accommodation types in Winchester

### Trending destinations on Expedia.co.uk

-   [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold)
-   [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district)
-   [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations)
-   [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations)
-   [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations)
-   [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations)
-   [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations)
-   [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations)
-   [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations)
-   [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations)
-   [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals)
-   [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
-   [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
-   [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
-   [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
-   [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
-   [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
-   [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
-   [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
-   [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
-   [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
-   [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
-   [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
-   [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
-   [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
-   [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

-   [Cabin Rentals in Winchester](https://expedia.co.uk/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation)
-   [B&B in Winchester](https://expedia.co.uk/Winchester-Bed-And-Breakfasts.d6056879-aaBedAndBreakfasts.Travel-Guide-Accommodation)
-   [Villas in Winchester](https://expedia.co.uk/Winchester-Villas.d6056879-aaVillas.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find holiday rentals in Winchester?

> Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

### What are some of the best holiday rentals that Winchester has to offer?

> [Terra Alta - Incredible River Views and Hot Tub!](https://www.expedia.co.uk/Charles-Town-Hotels-Terra-Alta-Hilltop-House-Overlooking-Shenandoah-Rapids.h46559723.Hotel-Information): This holiday home rental outside of Winchester is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

### How many holiday rentals will I find in Winchester?

> Choose from 17 Expedia holiday rentals in Winchester for a memorable holiday.

### What’s there to see and do in Winchester?

> Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

### What’s a holiday rental in Winchester like?

> Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.

### Expedia's Latest Trends

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General

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-   [Visit Ashburn](https://expedia.co.uk/Ashburn.dx6035055)
-   [Visit Arvonia](https://expedia.co.uk/Arvonia.dx3000355001)

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![QR code to download the app](data:image/png;base64,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)