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

Property grounds

1. Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (20 reviews)
"So cozy, perfect Vermont vacation!"
United States
Evan S.
$386 nightly
The price is $432
Aug 5 - Aug 6
Total with taxes and fees
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior detail

2. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
$223 nightly
The price is $250
Aug 4 - Aug 5
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Exterior

3. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
$404 nightly
The price is $457
Aug 11 - Aug 12
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior

4. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
$1,349 nightly
The price is $1,463
Aug 20 - Aug 21
Total with taxes and fees
2 Cabins & Sauna on Lake Monomonac
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 4 hours ago
Riverside Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
11,041
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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