Winchester Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Winchester holiday rentals

Exterior detail

Apartment in Peterborough

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (32 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is HK$704
HK$1,358 total
includes taxes & fees
15 Mar - 16 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Interior

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is HK$908
HK$1,574 total
includes taxes & fees
5 Mar - 6 Mar
Lovely 2nd Floor Apartment
Exterior

Cottage in Rindge

Finnish Cabin with Sauna on Lake Monomonac next to Mt. Monadnock
10.0 out of 10, Exceptional, (11 reviews)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is HK$1,120
HK$2,310 total
includes taxes & fees
3 Mar - 4 Mar
Finnish Cabin with Sauna on Lake Monomonac next to Mt. Monadnock
Exterior

Chalet in Rindge

Adirondack Cabin/House with Sauna on Lake Monomonac next to Mt. Monadnock
9.8 out of 10, Exceptional, (25 reviews)
"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"
United States
Leigh C.
The price is HK$1,323
HK$2,802 total
includes taxes & fees
3 Mar - 4 Mar
Adirondack Cabin/House with Sauna on Lake Monomonac next to Mt. Monadnock
Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
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 HK$1,056
HK$1,954 total
includes taxes & fees
18 Mar - 19 Mar
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

Chalet in Guilford

Vikings Villages Resort - Double Bed Room
The price is HK$1,760
HK$2,181 total
includes taxes & fees
3 Mar - 4 Mar
Vikings Villages Resort - Double Bed Room
Exterior

Apartment in Peterborough

Cozy & Bright Guest Suite
The price is HK$626
HK$1,485 total
includes taxes & fees
8 Mar - 9 Mar
Cozy & Bright Guest Suite
Outdoor spa tub

Holiday Home in Keene

Modern Downtown 12ppl Hot Tub Fire Pit Games
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is HK$1,064
HK$2,258 total
includes taxes & fees
3 Mar - 4 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games
Exterior

Cottage in Rindge

Grey Cabin/House with Sauna on Lake Monomonac next to Mt. Monadnock
7.6 out of 10, Good, (4 reviews)
"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"
United States
Brian
The price is HK$1,190
HK$2,641 total
includes taxes & fees
3 Mar - 4 Mar
Grey Cabin/House with Sauna on Lake Monomonac next to Mt. Monadnock
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,095
HK$2,410 total
includes taxes & fees
3 Mar - 4 Mar
Lake Whitingham & Mount Snow Area Village Apartment
Terrace/patio

Camping in Hinsdale

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
10.0 out of 10, Exceptional, (10 reviews)
"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."
United States
Jerry S.
The price is HK$751
HK$1,282 total
includes taxes & fees
7 Mar - 8 Mar
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
10.0 out of 10, Exceptional, (2 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 HK$978
HK$2,015 total
includes taxes & fees
20 Mar - 21 Mar
The Studio with a View. Bring your dog, too!
Exterior

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is HK$720
HK$1,407 total
includes taxes & fees
3 Mar - 4 Mar
2 Twin beds on 1st floor with En-suite bathroom.
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,601
HK$1,975 total
includes taxes & fees
3 Mar - 4 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Terrace/patio

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,169
HK$4,594 total
includes taxes & fees
3 Mar - 4 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Fridge, microwave, oven, stovetop

Holiday Home in Colrain

Colrain Spring into Adventure HotTub AirHockey Firepit
9.8 out of 10, Exceptional, (47 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is HK$2,216
HK$5,009 total
includes taxes & fees
3 Mar - 4 Mar
Colrain Spring into Adventure HotTub AirHockey Firepit
Smart TV, fireplace, printers

Cottage in Rindge

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (23 reviews)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is HK$1,197
HK$2,665 total
includes taxes & fees
8 Mar - 9 Mar
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

Chalet in East Dover

Chalet Mount Snow/Stratton Skiing/hiking
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,097
HK$3,668 total
includes taxes & fees
3 Mar - 4 Mar
Chalet Mount Snow/Stratton Skiing/hiking
Property grounds

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,228
HK$2,322 total
includes taxes & fees
1 Apr - 2 Apr
Family Friendly Hilltop House In Putney Vermont
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Hotel was very clean, breakfast was great and staff were very helpful and courteous."
Michael 2-night trip
Posted 6 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Rhododendron State Park, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Winchester has to offer?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Barden State Wildlife Management Area and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, New England Sweetwater Farm & Distillery and Winchester Speedpark are other places worth a visit.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.