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 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

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
$142 nightly
The price is $154
Nov 11 - Nov 12
Total with taxes and fees
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, (2 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.
$83 nightly
The price is $94
Nov 30 - Dec 1
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
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
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
$130 nightly
The price is $141
Nov 9 - Nov 10
Total with taxes and fees
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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
$196 nightly
The price is $219
Nov 9 - Nov 10
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A lake surrounded by trees, with a wooden deck leading to a white railing.

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

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (7 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
$253 nightly
The price is $274
Nov 9 - Nov 10
Total with taxes and fees
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

6. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$311 nightly
The price is $313
Nov 9 - Nov 10
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A house with a staircase leading to a porch, surrounded by snow and string lights.

7. 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, (13 reviews)
"Nice place"
United States
Tom
$237 nightly
The price is $265
Nov 12 - Nov 13
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

8. 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.
$345 nightly
The price is $387
Nov 18 - Nov 19
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

9. 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.
$411 nightly
The price is $446
Nov 9 - Nov 10
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

10. 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.
$321 nightly
The price is $348
Nov 9 - Nov 10
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

11. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
$184 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
Lovely 2nd Floor Apartment
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

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
9.8 out of 10, Exceptional, (49 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$134 nightly
The price is $145
Nov 9 - Nov 10
Total with taxes and fees
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 well-maintained garden.

13. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$149 nightly
The price is $166
Nov 9 - Nov 10
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

14. 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.
$241 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
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, (65 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.
$230 nightly
The price is $258
Nov 9 - Nov 10
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
$172 nightly
The price is $192
Nov 10 - Nov 11
Total with taxes and fees
Private room with En-suite bathroom Marigold Room
A wooden house with a porch lit by string lights, surrounded by snow.

17. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
$312 nightly
The price is $353
Nov 9 - Nov 10
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A wooden interior with a kitchen, bar area, and dining space.

18. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (8 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.
$212 nightly
The price is $237
Nov 18 - Nov 19
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

19. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
$109 nightly
The price is $123
Nov 9 - Nov 10
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A sunlit room with a large window, a bench, and a sofa.

20. 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)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
$337 nightly
The price is $366
Nov 10 - Nov 11
Total with taxes and fees
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
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

The Putney Inn

The Putney Inn

8/10 Good
"Pleasant, economical yet no-frills stay in an area with few inexpensive options. I'd stay here again."
Patrick 1-night trip
Posted 3 hours ago
The Putney Inn

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.