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

Winchester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester vacation 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 AED 202
AED 299 total
includes taxes & fees
17 Aug - 18 Aug
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, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AED 331
AED 578 total
includes taxes & fees
24 Aug - 25 Aug
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
9.4 out of 10, Exceptional, (6 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 AED 261
AED 483 total
includes taxes & fees
25 Aug - 26 Aug
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, (61 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 AED 426
AED 751 total
includes taxes & fees
17 Aug - 18 Aug
Lovely 2nd Floor Apartment
Living area

5. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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 AED 575
AED 1,627 total
includes taxes & fees
7 Sep - 8 Sep
Stunning Glass House nestled in the Vermont wilderness!
Exterior detail

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
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is AED 443
AED 1,036 total
includes taxes & fees
27 Aug - 28 Aug
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Coffee/tea maker, fridge, microwave, oven

7. 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 AED 671
AED 1,290 total
includes taxes & fees
18 Aug - 19 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Private kitchen

8. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is AED 459
AED 963 total
includes taxes & fees
7 Sep - 8 Sep
The Studio with a View. Bring your dog, too!
1 bedroom, desk, iron/ironing board, WiFi

9. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is AED 432
AED 782 total
includes taxes & fees
24 Aug - 25 Aug
Balcony Room in Victorian Home private bath
Property grounds

10. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AED 635
AED 1,167 total
includes taxes & fees
1 Sep - 2 Sep
Family Friendly Hilltop House In Putney Vermont
Terrace/patio

11. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AED 1,010
AED 1,254 total
includes taxes & fees
19 Aug - 20 Aug
Vikings Villages Resort - Double Bed Room
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, (41 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 364
AED 681 total
includes taxes & fees
26 Aug - 27 Aug
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Smart TV, fireplace, printers

13. 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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 AED 716
AED 1,459 total
includes taxes & fees
8 Sep - 9 Sep
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Coffee/tea maker, fridge, microwave, oven

14. 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 AED 782
AED 1,869 total
includes taxes & fees
17 Aug - 18 Aug
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

15. 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 AED 764
AED 1,172 total
includes taxes & fees
6 Sep - 7 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

16. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 792 total
includes taxes & fees
17 Aug - 18 Aug
Private bed with En-suite bathroom Marigold Room
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
9.8 out of 10, Exceptional, (10 reviews)
"Nice place"
United States
Tom
The price is AED 826
AED 1,054 total
includes taxes & fees
17 Aug - 18 Aug
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Exterior

18. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AED 508
AED 1,723 total
includes taxes & fees
31 Aug - 1 Sep
Chalet Mount Snow/Stratton Skiing/hiking
Iron/ironing board, WiFi, bed sheets

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is AED 591
AED 1,342 total
includes taxes & fees
24 Aug - 25 Aug
Cozy private 2 bed apartment in Shelburne Falls
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 AED 904
AED 1,391 total
includes taxes & fees
6 Sep - 7 Sep
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"The staff was helpful. The room was clean. There plenty of options for breakfast. Would stay again"
charlene 1-night trip
Posted 12 hours ago
Hampton Inn & Suites Greenfield

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Rhododendron State Park, or you can select a secluded option if you'd like a relaxing place to 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's the top vacation rental that Winchester has to offer?

Family Friendly Hilltop House In Putney Vermont: This vacation home rental outside of Winchester is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Winchester?

Cass Pond and Loring Field 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 vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a long or short time in Winchester. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.