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

Search the Best Cabins in Winchester

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winchester cabin rentals

Front of property

1. Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (37 reviews)
"Wonderful experience at the Windmill Motel. I highly recommend!"
United States
Crystal
$118 nightly
The price is $132
Aug 10 - Aug 11
Total with taxes and fees
Windmill Motel Restaurant
Exterior

2. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,001 reviews)
"Really great spot for the price, very happy with our short stay."
United States
Kyle
$121 nightly
The price is $133
Aug 11 - Aug 12
Total with taxes and fees
Hampton Inn Brattleboro
Exterior

3. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,000 reviews)
"The hotel was clean but very dated. Needs new flooring, paint etc. Staff was very nice."
United States
Pamela
$92 nightly
The price is $100
Aug 18 - Aug 19
Total with taxes and fees
Days Inn by Wyndham Keene NH
Exterior

4. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,001 reviews)
"All the staff were very helpful and friendly! Truly enjoyed my stay"
United States
Ramica
$135 nightly
The price is $146
Aug 2 - Aug 3
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior

5. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (840 reviews)
"Staff wasfriendly and my room is very clean"
United States
Michael
$124 nightly
The price is $136
Aug 23 - Aug 24
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
Property amenity

6. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Staff was very friendly, accommodating, and attentive to our needs. Room was clean and comfortable!"
United States
Helen
$149 nightly
The price is $162
Aug 2 - Aug 3
Total with taxes and fees
Best Western Plus Keene Hotel
Front of property - evening/night

7. The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.4 out of 10, Good, (1,000 reviews)
"The staff is so helpful and kind. There are sketchy people out there but overall the stay we are safe and we were able to sleep and rest."
United States
VINCENT JOEL
$77 nightly
The price is $85
Aug 18 - Aug 19
Total with taxes and fees
The Covered Bridge Inn
Exterior

8. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (397 reviews)
"Loved breakfast. Waffles were great."
United States
Leigh
$151 nightly
The price is $164
Aug 6 - Aug 7
Total with taxes and fees
Hampton Inn & Suites Keene
Exterior

9. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,003 reviews)
"One of our favorite hotels in Brattleboro. Clean, safe and the staff are super friendly."
United States
Marnie
$163 nightly
The price is $179
Aug 30 - Aug 31
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Exterior

10. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (942 reviews)
"Very nice boutique hotel. Close to everything. Staff was really well at check in and out. Definitely would go back"
United States
Donald
$131 nightly
The price is $144
Aug 9 - Aug 10
Total with taxes and fees
Latchis Hotel
Exterior

11. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (175 reviews)
"Wonderful stay"
United States
Justin
$129 nightly
The price is $140
Aug 5 - Aug 6
Total with taxes and fees
The Burrell House
Property grounds

12. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.8 out of 10, (29 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
$75 nightly
The price is $82
Aug 27 - Aug 28
Total with taxes and fees
Colonial Motel
Exterior

13. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (667 reviews)
"Clean room, staff is very friendly and attentive, pretty location right on the river."
United States
Monica
$144 nightly
The price is $156
Aug 30 - Aug 31
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
Deluxe Chalet | Terrace/patio

14. Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (217 reviews)
"Fantastic, beautiful property. We definitely want to visit again. Great for families."
United States
Otgonzaya
$201 nightly
The price is $219
Aug 24 - Aug 25
Total with taxes and fees
Vikings Villages Resort
Exterior

15. The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (378 reviews)
"Fantastic breakfast!"
United States
allisha
$180 nightly
The price is $202
Aug 2 - Aug 3
Total with taxes and fees
The Inn At Crumpin Fox
Exterior

16. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (788 reviews)
"My favorite hotel!!!!"
United States
Brian
$161 nightly
The price is $174
Aug 6 - Aug 7
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

17. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (789 reviews)
"Good value!"
United States
Brian
$74 nightly
The price is $81
Aug 3 - Aug 4
Total with taxes and fees
Travelodge by Wyndham Brattleboro VT
Exterior

18. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (665 reviews)
"Quiet and clean place to stay the night"
United States
Aigul
$84 nightly
The price is $93
Aug 30 - Aug 31
Total with taxes and fees
Econo Lodge Brattleboro South
Exterior

19. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (175 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
$148 nightly
The price is $161
Aug 2 - Aug 3
Total with taxes and fees
The Carriage Barn Inn
Front of property

20. Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (499 reviews)
"I had a wonderful stay. The pool was great and I had it to myself! My room was clean. I would definitely recommend!"
United States
Robert
$151 nightly
The price is $166
Aug 18 - Aug 19
Total with taxes and fees
Black Mountain Inn
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

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Nice property, well maintained and friendly staff. It would be nice to have coffee more prominently featured (and a snack or two?)"
sara 1-night trip
Posted 9 hours ago
Riverside Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
10,041
Accommodation
40 Cabin Rentals
Lowest Price
$81
Highest Price
$219

Frequently asked questions

What are the best cabins near Winchester?
Ranging from rustic and small to roomy and luxurious, you have 275 cabins to select from in and around Winchester. Standouts include Private And Artistic Cabin, Pet Friendly and Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East.
Are there cheap cabins in Winchester?
Whether you'd prefer to stay a hop and a skip from the water or on the top of a mountain, we have a fantastic variety of cheap cabins in Winchester to look into. Priced from $81 to $219 a night, your ideal cabin rental is waiting right here.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best mountain cabins near Winchester?
If you're in need of some crisp air and beautiful views, spend your next break in a Winchester mountain cabin. Immerse yourself in natural beauty at Cabin - Little House On The Lake In The Forest. This property has all you need for an enjoyable escape, such as a wood stove and a microwave oven. Alternatively, experience the mountain lifestyle at This Is It Fabulous Vermont Cabin W. It offers a wood stove, winery tours and more.
What are the best river cabins near Winchester?
If you're after a relaxing place to stay near the water, a Winchester river cabin is a terrific choice. Spend your break at Warm And Inviting Jamaica Cabin W and let all your worries scurry away downstream. Amenities here include a wood stove and a firepit. Another leading riverside escape is Cabin - Beautiful Mt Area With Beautiful Scenic Views. You'll have use of snowsport activities, skiing facilities and more.
What are the best cabins with pools near Winchester?
Put on your swimwear and splash around whenever you like when you choose one of our cabin rentals with a pool. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna is a top choice. A swimming pool and a porch are some of the other amenities you can take advantage of here. Or, take some time out at Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment. Along with its pool, this cabin offers on-site watersports and a swimming pool.
Can I find beach cabins near Winchester?
Enjoy sunset strolls along the sparkling sea when you reserve a Winchester beach cabin rental. Sun and fun should be your major priorities at Cabin - Relax, Reconnect And Enjoy. This seaside retreat offers on-site watersports and children's activities. Or, toss your bag down and make yourself at home at Lakefront - King - Petsok - W And D. Conveniences here include on-site watersports and clothes washing facilities.
What are the best weekend cabin rentals in Winchester?
Whether you're organizing a quick break with your darling or your entire family, we'll help you find an amazing weekend cabin getaway. One top example? Cabin - Little House On The Lake In The Forest. Featuring on-site watersports and a patio, you'll appreciate the natural surroundings here. This Is It Fabulous Vermont Cabin W is another terrific place where you can slow things down. Spend a few nights at this retreat which offers a patio and a firepit.
What are the best cabin prices in Winchester?
Whether you're on a budget or want to splurge on your next trip, you'll find what you're after on Expedia. At the moment, you can get a Winchester cabin from only $81 per night.
Can I find log cabins in Winchester?
Begin your day with a cup of coffee in your comfortable log cabin and then spend hours snow shoeing and hiking. Sound like heaven to you? Then you'll love Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Another getaway offering plenty of charm and comforts is Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment. Activities like swimming and mountain biking will add to your unforgettable experience here.
What are the highest-rated cabins in Winchester?
Travelers just keep returning to Cabin: Private Hot Tub, Walk To Pats Peak Ski Area. This knockout features a host of handy amenities including a patio and a fireplace. It won't take you long to figure out why Brook Road Cabin is also popular with vacationers. Conveniences like a barbecue grill and a kitchen will help make your vacation the best one yet.
Why should I book a cabin in Winchester?
Affordability, comfort, rustic charm — there are countless great reasons to choose a Winchester cabin. Get away from the noisy concrete jungle and wake up to the sweet sound of birdsong. There's a whole lot of adventure just a stone's throw away too. Whether you're traveling with family members, friends or your partner, you'll discover the perfect rental cabin on Expedia.
What are the top nature cabins in Winchester?
If you're able to haul yourself away from all the coziness and comforts of Warm And Inviting Jamaica Cabin W, adventure is in store. One of our most sought-after nature cabins in Winchester, it offers terrific access to the outdoors and amenities such as a fireplace and a barbecue grill. Cabin - Beautiful Mt Area With Beautiful Scenic Views is another recommendation. Charm, natural splendor, a patio, a fireplace ... They're just a few things to love about this place.
What are some of the best cabins near Vermont Country Store in Winchester?
You'll have Mother Nature as a neighbor at a cabin in Vermont Country Store. Cabin - Charming Fully Renovated One - Room Schoolhouse On 22+ Acres is one of the best. This escape also offers plenty of adventure, with nearby mountain biking and nearby sledding among the fun things to do in the area. Guests also love Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment. Go exploring and then head back to your cabin to enjoy its many comforts.

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