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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
$75 nightly
The price is $81
Oct 8 - Oct 9
Total with taxes and fees
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
$155 nightly
The price is $168
Oct 29 - Oct 30
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
$92 nightly
The price is $104
Oct 30 - Oct 31
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.

4. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (12 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.
$138 nightly
The price is $150
Oct 13 - Oct 14
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. 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, (2 reviews)
"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.
$273 nightly
The price is $296
Oct 8 - Oct 9
Total with taxes and fees
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
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, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
$367 nightly
The price is $398
Oct 13 - Oct 14
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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.
$449 nightly
The price is $487
Oct 14 - Oct 15
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
$207 nightly
The price is $231
Nov 3 - Nov 4
Total with taxes and fees
Lovely 2nd Floor Apartment
A blue house with a porch, a wooden bench, and a door.

9. 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
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
$221 nightly
The price is $247
Nov 2 - Nov 3
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

10. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$336 nightly
The price is $341
Oct 12 - Oct 13
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
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.
$229 nightly
The price is $257
Oct 20 - Oct 21
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

12. 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.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
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 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
$165 nightly
The price is $184
Nov 4 - Nov 5
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A wooden deck with outdoor furniture, a white door, and windows.

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, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
$364 nightly
The price is $395
Oct 14 - Oct 15
Total with taxes and fees
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A house by a lake with a dock and a boat.

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)
"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.
$253 nightly
The price is $275
Oct 8 - Oct 9
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A house with a staircase leading to a porch, surrounded by snow and string lights.

16. 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
$254 nightly
The price is $284
Oct 8 - Oct 9
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

17. 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, (46 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$189 nightly
The price is $205
Oct 8 - Oct 9
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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
10.0 out of 10, Exceptional, (6 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.
$238 nightly
The price is $266
Oct 25 - Oct 26
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

19. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$207 nightly
The price is $232
Oct 28 - Oct 29
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
A cabin with a covered porch, large windows, and snow-covered ground.

20. 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.
$309 nightly
The price is $335
Oct 19 - Oct 20
Total with taxes and fees
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.
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Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

8/10 Good
"Nice area; motel needs some TLC. Spent three nights while on a sightseeing trip. Overall enjoyed our stay."
Carolyn 3-night trip
Posted 1 day 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 $81 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.