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Winchester Holiday Rentals

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Holiday Rentals in Winchester

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is AU$394
includes taxes & fees
27 Oct - 28 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!
Finnish Cabin with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (10)
"This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again."
United States
Cintromix
The price is AU$518
includes taxes & fees
23 Oct - 24 Oct
Finnish Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (24)
"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 AU$549
includes taxes & fees
26 Oct - 27 Oct
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Lake Whitingham & Mount Snow Area Village Apartment
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 AU$471
includes taxes & fees
26 Oct - 27 Oct
Lake Whitingham & Mount Snow Area Village Apartment
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (19)
"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 AU$562
includes taxes & fees
4 Nov - 5 Nov
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AU$371
includes taxes & fees
5 Nov - 6 Nov
Family Friendly Hilltop House In Putney Vermont
Grey Cabin with Sauna on Lake Monomonac
2.0 star property
7.6 out of 10, Good, (4)
"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 AU$522
includes taxes & fees
27 Oct - 28 Oct
Grey Cabin with Sauna on Lake Monomonac
Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AU$654
includes taxes & fees
2 Nov - 3 Nov
Mountain Chalet mins from Mt Snow Skiing/hiking
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is AU$323
includes taxes & fees
4 Nov - 5 Nov
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (41)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is AU$312
includes taxes & fees
28 Oct - 29 Oct
Lovely 2nd Floor Apartment
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
10.0 out of 10, Exceptional, (4)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
The price is AU$320
includes taxes & fees
31 Oct - 1 Nov
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (27)
"great location"
United States
Kevin M.
The price is AU$286
includes taxes & fees
3 Nov - 4 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Stunning Glass House nestled in the Vermont wilderness!
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 AU$659
includes taxes & fees
5 Nov - 6 Nov
Stunning Glass House nestled in the Vermont wilderness!
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
10.0 out of 10, Exceptional, (20)
"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 AU$941
includes taxes & fees
2 Nov - 3 Nov
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
United States
Evan C.
The price is AU$454
includes taxes & fees
3 Nov - 4 Nov
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Couples 2 Bedroom Retreat-Close to Shelburne Falls
10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
The price is AU$582
includes taxes & fees
28 Oct - 29 Oct
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Vikings Villages Resort - Double Bed Room
The price is AU$573
includes taxes & fees
2 Nov - 3 Nov
Vikings Villages Resort - Double Bed Room
Charming Home Walk to Downtown!
10.0 out of 10, Exceptional, (1)
"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 AU$1,086
includes taxes & fees
29 Oct - 30 Oct
Charming Home Walk to Downtown!
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
The price is AU$354
includes taxes & fees
27 Oct - 28 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 favourite 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 depend 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 AU$312 per night. Entering your travel dates in the search wizard might find you 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?

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This holiday home rental outside of Winchester is located on a river, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Winchester?

Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, Pisgah State Park and New England Sweetwater Farm & Distillery 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.