A snow-covered town with a river running through it, surrounded by mountains and trees.

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchester holiday rentals

A grassy field with trees and a red building in the background.

1. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AU$105
includes taxes & fees
2 Nov - 3 Nov
2 private mountain RV pads for rent. Full hook ups
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

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, (20 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AU$221
includes taxes & fees
2 Nov - 3 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (1 review)
"Cozy, clean and peaceful spot! Host was responsive and helpful."
United States
Maggie G.
The price is AU$137
includes taxes & fees
30 Nov - 1 Dec
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, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
The price is AU$204
includes taxes & fees
2 Nov - 3 Nov
Yurt Oasis in the woods of Hinsdale, NH
A blue house with a porch, a wooden bench, and a door.

5. 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
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is AU$318
includes taxes & fees
9 Nov - 10 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A lake surrounded by trees, with a wooden deck leading to a white railing.

6. 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, (7 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is AU$395
includes taxes & fees
2 Nov - 3 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

7. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 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.
The price is AU$637
includes taxes & fees
8 Nov - 9 Nov
Stunning Glass House nestled in the Vermont wilderness!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

8. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AU$448
includes taxes & fees
2 Nov - 3 Nov
Vikings Villages Resort - Double Bed Room
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

9. 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.
The price is AU$503
includes taxes & fees
2 Nov - 3 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

10. 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, (5 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.
The price is AU$644
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

11. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is AU$342
includes taxes & fees
2 Nov - 3 Nov
Lovely 2nd Floor Apartment
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.
The price is AU$372
includes taxes & fees
9 Nov - 10 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A garden with a wooden pergola, purple flowers, and a river view.

13. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 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.
The price is AU$378
includes taxes & fees
2 Nov - 3 Nov
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

14. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is AU$245
includes taxes & fees
4 Nov - 5 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

15. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$271
includes taxes & fees
8 Nov - 9 Nov
Private room with En-suite bathroom Marigold Room
A wooden interior with a kitchen, bar area, and dining space.

16. 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, (7 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 AU$319
includes taxes & fees
8 Nov - 9 Nov
The Studio with a View. Bring your dog, too!
A house with a staircase leading to a porch, surrounded by snow and string lights.

17. 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
The price is AU$389
includes taxes & fees
12 Nov - 13 Nov
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.

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, (48 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AU$252
includes taxes & fees
18 Nov - 19 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A sunlit room with a large window, a bench, and a sofa.

19. 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.
The price is AU$526
includes taxes & fees
2 Nov - 3 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Property grounds

20. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (2 reviews)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is AU$680
includes taxes & fees
2 Nov - 3 Nov
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
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

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent
"Mahi was a wonderful host. I recommend I recommend if you stay in Brattleboro that you stay here. We will be back."
Stacey 1-night trip
Posted 9 hours ago
Travelodge by Wyndham Brattleboro VT

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$105 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?

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 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 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.