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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winchester vacation 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 ￥8,655
￥12,806 total
includes taxes & fees
Oct 5 - Oct 6
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 ￥14,163
￥24,759 total
includes taxes & fees
Oct 5 - Oct 6
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (10 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 ￥13,597
￥23,289 total
includes taxes & fees
Oct 6 - Oct 7
Yurt Oasis in the woods of Hinsdale, NH
A blue house with a porch, a wooden bench, and a door.

4. 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)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥14,169
￥37,983 total
includes taxes & fees
Oct 5 - Oct 6
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A room with white paneled walls, a wooden bench, a teal cushion, a vase with flowers, a framed picture, and a shelf with books and a small electronic device.

5. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is ￥13,885
￥19,249 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Vermont Tiny Home Get Away
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

6. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 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 ￥21,874
￥36,563 total
includes taxes & fees
Oct 22 - Oct 23
Lovely 2nd Floor Apartment
A house by a lake with a dock and a boat.

7. 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)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is ￥31,018
￥47,485 total
includes taxes & fees
Oct 12 - Oct 13
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. 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, (1 review)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is ￥37,533
￥46,528 total
includes taxes & fees
Oct 6 - Oct 7
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A wooden deck with outdoor furniture, a white door, and windows.

9. 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 ￥30,687
￥61,642 total
includes taxes & fees
Oct 18 - Oct 19
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A wooden interior with a kitchen, bar area, and dining space.

10. 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, (5 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 ￥20,254
￥41,543 total
includes taxes & fees
Oct 5 - Oct 6
The Studio with a View. Bring your dog, too!
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 ￥43,277
￥53,709 total
includes taxes & fees
Oct 13 - Oct 14
Vikings Villages Resort - Double Bed Room
A wooden house with a porch lit by string lights, surrounded by snow.

12. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥20,672
￥72,418 total
includes taxes & fees
Oct 6 - Oct 7
Chalet Mount Snow/Stratton Skiing/hiking
A garden with a wooden pergola, purple flowers, and a river view.

13. 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 ￥20,962
￥41,456 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase, and a small garden area.

14. 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
Central Large 2-bedrooms with office in Keene
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

15. 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 ￥38,241
￥66,080 total
includes taxes & fees
Oct 8 - Oct 9
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is ￥16,996
￥31,465 total
includes taxes & fees
Oct 21 - Oct 22
Rose room Victorian home queen bed private bath
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

17. 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 ￥26,763
￥46,725 total
includes taxes & fees
Oct 20 - Oct 21
Wellness Getaway with a Personal Sauna, and Private River Beach!
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥18,884
￥33,925 total
includes taxes & fees
Oct 7 - Oct 8
Private bed with En-suite bathroom Marigold Room
A house with a staircase leading to a porch, surrounded by snow and string lights.

19. 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 ￥35,408
￥45,001 total
includes taxes & fees
Oct 8 - Oct 9
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

20. 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 ￥31,329
￥76,867 total
includes taxes & fees
Oct 26 - Oct 27
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Very unique spot. We planned this last minute getaway after another trip was canceled. The cabins are so cute. awe did not partake in the activities but wish we had another day. We did see sheep. Quiet, cute, different."
Elizabeth 2-night trip
Posted 6 hours ago
Vikings Villages Resort

Find out more about Winchester

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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.