An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Search Holiday Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester holiday rentals

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is £234
includes taxes & fees
23 Jun - 24 Jun
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is £234
includes taxes & fees
23 Jun - 24 Jun
The Winchester

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (50 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is £162
includes taxes & fees
23 Jun - 24 Jun
Conveniently Located ~ WiFi ~ Central Heat & Air.

Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3

Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3
Stanton
9.6 out of 10, Exceptional, (14 reviews)
"Exactly as advertised and management was super responsive "
United States
Chris H.
The price is £102
includes taxes & fees
24 Jun - 25 Jun
Furnished Glamping Tent/2 Queen Beds/Red River Access - Majestic Mallard - #3

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,935 reviews)
"Great area Nice place to stay"
United States
Julie
The price is £102
includes taxes & fees
19 Jul - 20 Jul
Natural Bridge State Resort Park

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (324 reviews)
"Great stay! Loved the private driveway. "
United States
Emily N.
The price is £237
includes taxes & fees
23 Jun - 24 Jun
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveller
The price is £236
includes taxes & fees
23 Jun - 24 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (36 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is £145
includes taxes & fees
23 Jun - 24 Jun
Mountaintop Cottage

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.

Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.
Slade
8.2 out of 10, Very good, (30 reviews)
"The home had a great view and was very close to anything you'd love to do in the area. "
United States
Caleb H.
Discover Serenity at Hidden Ridge, Hot Tub, Satellite TV, firepit.

East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (66 reviews)
"Absolutely beautiful accommodations that are within walking distance to the downtown Georgetown area. Jane and her pooch Sandy were divine. Will stay there again in the future."
United States
Laura ..
The price is £177
includes taxes & fees
29 Jun - 30 Jun
East Suite-🕊️ at Bleubird Studio, Walk to Downtown

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (110 reviews)
"great place!"
United States
Ava G.
The price is £147
includes taxes & fees
6 Jul - 7 Jul
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (48 reviews)
"The cabin was perfect for us! It was comfortable and had everything we needed. The back porch was awesome with a gorgeous view! "
United States
Patrece M.
The price is £161
includes taxes & fees
6 Jul - 7 Jul
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (131 reviews)
"Cute little spot to stay, the view and hot tub is incredible, both day & night. "
United States
Tawny Freber- S.
The price is £215
includes taxes & fees
24 Jun - 25 Jun
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (77 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is £149
includes taxes & fees
23 Jun - 24 Jun
Mountain Memories Cabin

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (367 reviews)
"Great spot for weekend getaway. "
United States
Liz A.
The price is £227
includes taxes & fees
25 Jun - 26 Jun
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Stanton
10.0 out of 10, Exceptional, (27 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is £215
includes taxes & fees
23 Jun - 24 Jun
PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
The price is £208
includes taxes & fees
23 Jun - 24 Jun
"Cardinal Crest" - Overlook Dome 002 in RRG

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (165 reviews)
"Everything was amazing Highly Recommend"
United States
Jason L.
The price is £215
includes taxes & fees
23 Jun - 24 Jun
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (112 reviews)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveller
The price is £139
includes taxes & fees
16 Jul - 17 Jul
Unique Stay in a 1907 Log Cabin on The Kentucky River

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (13 reviews)
"Fun place to stay for 2!"
United States
Bob R.
The price is £238
includes taxes & fees
23 Jun - 24 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

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, cottages, apart-hotels, cabins, 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 £102 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. 

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

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

Luxe Home Downtown - Sleeps 6. Off-street parking: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winchester?

Expedia has 5 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail are other places to visit while you're in town.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.