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Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is NZ$362
includes taxes & fees
11 Jan - 12 Jan
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is NZ$444
includes taxes & fees
15 Jan - 16 Jan
Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 NZ$529
includes taxes & fees
3 Jan - 4 Jan
Lake Whitingham & Mount Snow Area Village Apartment
10.0 out of 10, Exceptional, (22)
"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 NZ$630
includes taxes & fees
12 Jan - 13 Jan
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is NZ$349
includes taxes & fees
5 Jan - 6 Jan
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (30)
"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 NZ$268
includes taxes & fees
5 Jan - 6 Jan
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is NZ$717
includes taxes & fees
5 Jan - 6 Jan
Mountain Chalet mins from Mt Snow Skiing/hiking
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is NZ$423
includes taxes & fees
5 Jan - 6 Jan
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is NZ$821
includes taxes & fees
13 Jan - 14 Jan
Terrific 3-bedroom unit in charming Leverett with AC
The price is NZ$476
includes taxes & fees
2 Feb - 3 Feb
Rose wisteria 4 guests 2 bedrooms-full+queen beds
2.0 star property
The price is NZ$401
includes taxes & fees
4 Jan - 5 Jan
The Studio with a View. Bring your dog, too!

Holiday Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"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 NZ$480
includes taxes & fees
4 Jan - 5 Jan
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (59)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is NZ$531
includes taxes & fees
5 Jan - 6 Jan
Family Friendly Hilltop House In Putney Vermont
10.0 out of 10, Exceptional, (25)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is NZ$912
includes taxes & fees
6 Jan - 7 Jan
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
2.0 star property
The price is NZ$889
includes taxes & fees
5 Jan - 6 Jan
Secluded Vermont Chalet w/ Sweeping Mountain Views
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is NZ$1,042
includes taxes & fees
5 Jan - 6 Jan
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is NZ$770
includes taxes & fees
19 Jan - 20 Jan
Stunning Glass House nestled in the Vermont wilderness!
10.0 out of 10, Exceptional, (21)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is NZ$1,364
includes taxes & fees
12 Jan - 13 Jan
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
The price is NZ$728
includes taxes & fees
10 Jan - 11 Jan
Vikings Villages Resort - Double Bed Room
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is NZ$1,118
includes taxes & fees
5 Jan - 6 Jan
FaLL Western Mass Getaway-Airhockey-Firepit
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$349 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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. 

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?

Birch Point and Barden State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. While here, Pisgah State Park and Ashuelot River 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.