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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winchester vacation rentals

Outdoor dining

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
Aug 10 - Aug 11
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
Terrace/patio

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, (16 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$145 nightly
The price is $157
Aug 10 - Aug 11
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
$118 nightly
The price is $127
Aug 31 - Sep 1
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
Interior

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 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.
$181 nightly
The price is $202
Aug 10 - Aug 11
Total with taxes and fees
Lovely 2nd Floor Apartment
Living area

5. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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.
$390 nightly
The price is $436
Sep 7 - Sep 8
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Coffee/tea maker, fridge, microwave, oven

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
$362 nightly
The price is $393
Aug 16 - Aug 17
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Exterior detail

7. 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)
"We had a great"
United States
Meredith B.
$252 nightly
The price is $281
Sep 9 - Sep 10
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Terrace/patio

8. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$335 nightly
The price is $340
Aug 11 - Aug 12
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
Coffee/tea maker, fridge, microwave, oven

9. 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.
$442 nightly
The price is $480
Aug 10 - Aug 11
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Property grounds

10. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (62 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
$288 nightly
The price is $323
Sep 8 - Sep 9
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Exterior

11. 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, (10 reviews)
"Nice place"
United States
Tom
$254 nightly
The price is $284
Aug 10 - Aug 11
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Smart TV, fireplace, printers

12. 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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.
$363 nightly
The price is $394
Sep 8 - Sep 9
Total with taxes and fees
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Private kitchen

13. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
$233 nightly
The price is $261
Sep 7 - Sep 8
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Terrace/patio

14. 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)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
$405 nightly
The price is $458
Aug 11 - Aug 12
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
1 bedroom, desk, iron/ironing board, WiFi

15. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
$192 nightly
The price is $214
Aug 30 - Aug 31
Total with taxes and fees
Balcony Room in Victorian Home private bath
Iron/ironing board, WiFi, bed sheets

16. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
$327 nightly
The price is $365
Aug 10 - Aug 11
Total with taxes and fees
Cozy private 2 bed apartment in Shelburne Falls
House (3 Bedrooms) | Front of property

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

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$395 nightly
The price is $435
Aug 11 - Aug 12
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior detail

18. 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, (40 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$186 nightly
The price is $202
Aug 26 - Aug 27
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

19. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$365 nightly
The price is $413
Aug 13 - Aug 14
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

20. 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)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
$290 nightly
The price is $315
Sep 6 - Sep 7
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
"I feel the 8.6 is much too overrated. A 7, maybe. Old building, needs a facelift. Clean, but does not feel as a happy place. Old rugs. Very dark ( but clean) rooms. Felt like in a cave. Manager had no people skills, not welcoming. Will not stay there again. Put a little money into the place!"
irina 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 $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?

Family Friendly Hilltop House In Putney Vermont: This vacation home rental outside of Winchester is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Winchester?

Cass Pond and Loring Field are a couple of lovely local spots to get outside and enjoy nature. While here, Winchester Speedpark and Pisgah State Park 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.