A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester holiday rentals

A lakeside park with picnic tables and a concrete walkway.

1. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is £65
includes taxes & fees
12 Oct - 13 Oct
2 private mountain RV pads for rent. Full hook ups
A rustic cabin with a covered porch, a small shed, and outdoor seating.

2. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is £130
includes taxes & fees
25 Oct - 26 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is £82
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

4. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (12 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is £115
includes taxes & fees
13 Oct - 14 Oct
Yurt Oasis in the woods of Hinsdale, NH
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (3 reviews)
"The property was adorable, clean and had everything we needed. Even though it rained all weekend we still had the best time. Great, private location with amazing views and close to downtown Keene. The host was very responsive and made sure we were comfortable and had all the info we needed."
United States
Marie M.
The price is £223
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A blue house with a porch, a wooden bench, and a door.

6. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is £169
includes taxes & fees
4 Nov - 5 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A two-story house with a front porch, a staircase, and a small garden area.

7. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (8 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is £168
includes taxes & fees
19 Oct - 20 Oct
Central Large 2-bedrooms with office in Keene
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

8. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is £393
includes taxes & fees
8 Nov - 9 Nov
Stunning Glass House nestled in the Vermont wilderness!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

9. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is £176
includes taxes & fees
1 Nov - 2 Nov
Lovely 2nd Floor Apartment
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

10. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is £373
includes taxes & fees
12 Oct - 13 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

11. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is £263
includes taxes & fees
12 Oct - 13 Oct
Vikings Villages Resort - Double Bed Room
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

12. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is £287
includes taxes & fees
13 Oct - 14 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

13. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is £219
includes taxes & fees
3 Nov - 4 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A garden with a wooden pergola, purple flowers, and a river view.

14. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is £204
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A house with a staircase leading to a porch, surrounded by snow and string lights.

15. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (13 reviews)
"Nice place"
United States
Tom
The price is £218
includes taxes & fees
14 Oct - 15 Oct
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

16. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is £146
includes taxes & fees
4 Nov - 5 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A wooden interior with a kitchen, bar area, and dining space.

17. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (6 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is £207
includes taxes & fees
25 Oct - 26 Oct
The Studio with a View. Bring your dog, too!
A wooden deck with outdoor furniture, a white door, and windows.

18. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is £299
includes taxes & fees
14 Oct - 15 Oct
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A house by a lake with a dock and a boat.

19. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
The price is £235
includes taxes & fees
20 Oct - 21 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

20. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (47 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is £172
includes taxes & fees
14 Oct - 15 Oct
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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.
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Top Winchester Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"For being a historic hotel this place was nice. Sound machines in the rooms to make up for being on a busy street. Fan in the room to help with circulation. Historic charm in great walkable downtown location. Parking lot was small but there is additional parking in a city lot and on the street."
Jason 1-night trip
Posted 2 hours ago
Latchis Hotel

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 £65 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

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Rhododendron State Park, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Winchester. Make sure you have time to check out the forests and waterfront during your trip.

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

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Birch Point and Cass Pond are a couple of lovely local spots to get outside and enjoy nature. While here, Winchester Speedpark and New England Sweetwater Farm & Distillery are other places worth a visit.

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 laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks 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 an attractive choice for family trips.