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

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester holiday rentals

Outdoor dining

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 HK$431
HK$638 total
includes taxes & fees
14 Sept - 15 Sept
2 private mountain RV pads for rent. Full hook ups
Terrace/patio

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, (18 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is HK$748
HK$1,279 total
includes taxes & fees
8 Sept - 9 Sept
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (8 reviews)
"Cozy and clean yurt in the woods surrounded by sounds of hooting owls and a super friendly and help host made for the perfect family weekend. Can’t wait to plan another stay. Made roughing it not rough at all. "
United States
Allisha C.
The price is HK$797
HK$1,290 total
includes taxes & fees
9 Sept - 10 Sept
Yurt Oasis in the woods of Hinsdale, NH
Interior

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is HK$910
HK$1,586 total
includes taxes & fees
7 Sept - 8 Sept
Lovely 2nd Floor Apartment
Coffee/tea maker, fridge, microwave, oven

5. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,517
HK$2,820 total
includes taxes & fees
10 Sept - 11 Sept
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Terrace/patio

6. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,156
HK$2,667 total
includes taxes & fees
7 Sept - 8 Sept
Vikings Villages Resort - Double Bed Room
Coffee/tea maker, fridge, microwave, oven

7. 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 HK$1,505
HK$3,760 total
includes taxes & fees
7 Sept - 8 Sept
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Property grounds

8. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 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 HK$1,122
HK$2,161 total
includes taxes & fees
14 Sept - 15 Sept
Family Friendly Hilltop House In Putney Vermont
Exterior detail

9. 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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is HK$1,106
HK$2,382 total
includes taxes & fees
29 Sept - 30 Sept
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Terrace/patio

10. 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 HK$1,529
HK$3,096 total
includes taxes & fees
15 Sept - 16 Sept
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Exterior

11. 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)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is HK$1,374
HK$2,171 total
includes taxes & fees
7 Sept - 8 Sept
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior detail

12. 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
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is HK$917
HK$1,608 total
includes taxes & fees
7 Sept - 8 Sept
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Living area

13. 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 HK$2,532
HK$5,110 total
includes taxes & fees
24 Sept - 25 Sept
Stunning Glass House nestled in the Vermont wilderness!
Iron/ironing board, WiFi, bed sheets

14. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is HK$1,262
HK$2,864 total
includes taxes & fees
7 Sept - 8 Sept
Cozy private 2 bed apartment in Shelburne Falls
Exterior

15. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is HK$811
HK$1,511 total
includes taxes & fees
7 Sept - 8 Sept
Rose room Victorian home queen bed private bath
Exterior

16. 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 HK$1,607
HK$2,705 total
includes taxes & fees
6 Oct - 7 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior

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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
The price is HK$1,948
HK$2,456 total
includes taxes & fees
9 Sept - 10 Sept
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior

18. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$941
HK$1,673 total
includes taxes & fees
13 Sept - 14 Sept
Private bed with En-suite bathroom Marigold Room
Smart TV

19. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is HK$1,646
HK$2,468 total
includes taxes & fees
17 Sept - 18 Sept
Cozy Tiny House on Main Street. Fully Renovated.
Exterior

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
The price is HK$1,750
HK$2,732 total
includes taxes & fees
8 Sept - 9 Sept
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 18 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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?

5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio 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 garden, a selection of games and 1 hot tub 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 Pisgah State Park 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.