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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

A wooden deck with a rustic outdoor seating area, including Adirondack chairs and a small table, surrounded by a forested area with a wooden structure in the background.

1. 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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥14,374
￥23,741 total
includes taxes & fees
Nov 17 - Nov 18
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (3 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is ￥11,499
￥15,160 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Vermont Tiny Home Get Away
A wooden deck with a grill and propane tank, surrounded by trees.

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
The price is ￥14,805
￥23,341 total
includes taxes & fees
Nov 18 - Nov 19
Yurt Oasis in the woods of Hinsdale, NH
A rustic log cabin with a steeply pitched roof, a prominent door with a decorative cross, and a small porch with two Adirondack chairs.

4. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥43,920
￥51,645 total
includes taxes & fees
Nov 16 - Nov 17
Vikings Villages Resort - Double Bed Room
A deck with a round table and chairs, surrounded by a white railing, overlooking a lake.

5. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (8 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is ￥38,091
￥44,968 total
includes taxes & fees
Nov 16 - Nov 17
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (28 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is ￥34,497
￥59,091 total
includes taxes & fees
Nov 19 - Nov 20
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A covered outdoor deck with a grill, seating area, and a blue shed in the background.

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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 ￥30,664
￥73,126 total
includes taxes & fees
Nov 16 - Nov 17
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A wooden door with a mirror, a small basket with dried flowers, and a light switch on the wall.

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is ￥24,436
￥37,999 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 2nd Floor Apartment
A covered porch with white railings, two wicker chairs, and potted plants.

9. 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, (16 reviews)
"Nice place"
United States
Tom
The price is ￥35,935
￥43,529 total
includes taxes & fees
Nov 18 - Nov 19
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A blue house with a porch, a wooden bench, and a door.

10. 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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is ￥14,086
￥36,428 total
includes taxes & fees
Nov 18 - Nov 19
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A house by a lake with a dock and a boat.

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (14 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 ￥26,232
￥39,900 total
includes taxes & fees
Nov 16 - Nov 17
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern kitchen with a wooden island, a dining area with a sofa, and a living room with a TV and artwork.

12. 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)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
United States
David W.
The price is ￥33,539
￥47,841 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Tiny House on Main Street. Fully Renovated.
A wooden staircase leading up to a wooden bridge in a forested area.

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 ￥27,151
￥45,256 total
includes taxes & fees
Nov 23 - Nov 24
Wellness Getaway with a Personal Sauna, and Private River Beach!
A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

14. 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, (26 reviews)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is ￥31,143
￥59,785 total
includes taxes & fees
Nov 16 - Nov 17
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A garden with a wooden pergola, purple flowers, and a river view.

15. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (66 reviews)
"Had a perfect, relaxing stay in this gorgeous spot. Everything was terrific. Highly recommend!"
United States
Wendy B.
The price is ￥26,033
￥45,971 total
includes taxes & fees
Nov 17 - Nov 18
Family Friendly Hilltop House In Putney Vermont
A library building with a brick facade, large windows, and a sidewalk in front.

16. 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, (49 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is ￥13,080
￥24,935 total
includes taxes & fees
Nov 17 - Nov 18
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A cabin with a central deck, two rocking chairs, and a small table.

17. 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 ￥33,419
￥50,123 total
includes taxes & fees
Nov 16 - Nov 17
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A bridge over a pond surrounded by dense vegetation and trees.

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is ￥28,604
￥44,553 total
includes taxes & fees
Nov 22 - Nov 23
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

19. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"An outstanding property filled with history, beautiful furniture and highly recommended"
United States
Eileen L.
The price is ￥51,906
￥59,087 total
includes taxes & fees
Nov 17 - Nov 18
Enjoy your stay in an antique home in an antique toy museum!
A room with a green floor, a white door, and a window with blinds.

20. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is ￥25,713
￥55,483 total
includes taxes & fees
Nov 30 - Dec 1
Spacious & Cozy Ground Floor 2/3 Bed private suite
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Clean room. Nice breakfast ladies. Complimentary Soup in the evening."
Davina 3-night trip
Posted 15 hours ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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 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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This vacation home rental outside of Winchester is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 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.