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

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 AED 202
AED 299 total
includes taxes & fees
4 Oct - 5 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 AED 331
AED 578 total
includes taxes & fees
5 Oct - 6 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AED 271
AED 389 total
includes taxes & fees
30 Oct - 31 Oct
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
9.4 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 AED 311
AED 536 total
includes taxes & fees
5 Oct - 6 Oct
Yurt Oasis in the woods of Hinsdale, NH
A blue house with a porch, a wooden bench, and a door.

5. 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 AED 327
AED 883 total
includes taxes & fees
5 Oct - 6 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 AED 511
AED 853 total
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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 AED 727
AED 1,789 total
includes taxes & fees
26 Oct - 27 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A room with a wicker chair, a small table with a lamp, and a window with a view of greenery.

8. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AED 1,010
AED 1,249 total
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.

9. 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 AED 841
AED 1,479 total
includes taxes & fees
22 Oct - 23 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.

10. 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 AED 588
AED 1,045 total
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.

11. 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 AED 489
AED 968 total
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

12. 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 AED 401
AED 731 total
includes taxes & fees
27 Oct - 28 Oct
2 Twin beds on 1st floor with En-suite bathroom.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

13. 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 AED 876
AED 1,086 total
includes taxes & fees
4 Oct - 5 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

14. 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, (45 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AED 374
AED 684 total
includes taxes & fees
4 Oct - 5 Oct
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

15. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 780 total
includes taxes & fees
26 Oct - 27 Oct
Private bed with En-suite bathroom Marigold Room
A wooden interior with a kitchen, bar area, and dining space.

16. 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 AED 463
AED 959 total
includes taxes & fees
5 Oct - 6 Oct
The Studio with a View. Bring your dog, too!
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

17. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
The price is AED 389
AED 1,556 total
includes taxes & fees
5 Oct - 6 Oct
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A house with a staircase leading to a porch, surrounded by snow and string lights.

18. 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 AED 826
AED 1,050 total
includes taxes & fees
8 Oct - 9 Oct
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is AED 724
AED 1,108 total
includes taxes & fees
13 Oct - 14 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

20. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AED 566
AED 722 total
includes taxes & fees
12 Oct - 13 Oct
The Eagles Wing at The CHM - Private Apartment
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked. The room was spacious, quiet and comfortable. The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....) Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot."
Thomas 1-night trip
Posted less than an hour ago
Hampton Inn Brattleboro

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.