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

Find Cabins in Winchester for Rent from CA $365

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester cabin rentals

A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

1. 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 CA $226
CA $407 total
includes taxes & fees
Nov 3 - Nov 4
Wellness Getaway with a Personal Sauna, and Private River Beach!
A rustic building with a wooden deck, string lights, and a window overlooking a garden.

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, (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 CA $172
CA $365 total
includes taxes & fees
Nov 2 - Nov 3
The Studio with a View. Bring your dog, too!
A wooden cabin with large windows and a covered porch.

3. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is CA $270
CA $439 total
includes taxes & fees
Oct 20 - Oct 21
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A rustic cabin with a signpost indicating directions to various destinations.

4. 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, (1 review)
"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 CA $247
CA $688 total
includes taxes & fees
Oct 21 - Oct 22
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A cabin with a porch, picnic table, and a bike parked in front.

5. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
The price is CA $316
CA $496 total
includes taxes & fees
Oct 20 - Oct 21
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A cabin by a lake with a dock, surrounded by dense trees.

6. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is CA $805
CA $1,277 total
includes taxes & fees
Nov 15 - Nov 16
2 Cabins & Sauna on Lake Monomonac
A two-story cabin with a balcony, surrounded by a forest.

7. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is CA $316
CA $906 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Cedar Cabin 8 Min to Mount Snow
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

The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Everything was nice, clean and comfortable - the bathroom was a little tight (door hit the toilet) but other than that would totally stay again."
Sarah 1-night trip
Posted 3 hours ago
The Inn At Crumpin Fox

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
35
Accommodation
36 Cabin Rentals
Lowest Price
CA $365
Highest Price
CA $1,277

Frequently asked questions

What are the best cabins near Winchester?
Vacation in one of our 276 cabins in Winchester and be rewarded with striking scenery, outdoor adventure and long-lasting memories. Private And Artistic Cabin, Pet Friendly is the place to go for an unplugged getaway. Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East is another good choice if you'd love to spend time in Mother Nature.
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 CA $365 to CA $1,277 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 craving crisp air and stunning views, escape the city and stay in a Winchester mountain cabin. Get your head in the clouds at Cabin - Little House On The Lake In The Forest. This lofty rental has all the ingredients for a fantastic escape, including a wood stove and a microwave oven. Alternatively, experience a taste of 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 looking for a comfy escape by the water, a Winchester river cabin will be just the thing. Put your feet up at Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet and let any worries drift downstream. Handy amenities here include a wood stove and snowsport activities. Another superb riverside retreat is Warm And Inviting Jamaica Cabin W. It offers a wood stove, a firepit and more.
What are the best cabins with pools near Winchester?
If you love the thought of every day being a pool day, make a break for Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. It's one of our top cabin rentals with a pool near Winchester and offers amenities like a swimming pool and a porch. Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet is another superb place to spend lazy days poolside. A porch, a patio and fun times are up for grabs here.
Can I find beach cabins near Winchester?
Wake up and be moments from a beautiful shoreline when you lock in a stay at a Winchester beach cabin rental. Sun, fun and family time should be your main priorities at Cabin - Relax, Reconnect And Enjoy. It offers on-site watersports and children's activities. Or, throw your bag down and spend a few nights at Cabin - Lakefront - King - Petsok - W And D. Handy amenities here include on-site watersports and clothes washing facilities.
What are the best weekend cabin rentals in Winchester?
Whether you're planning a mini break with your beau or the entire family, we'll help you find your dream weekend cabin getaway. One superb example? Cabin - Little House On The Lake In The Forest. Featuring on-site watersports and a patio, you'll adore the natural surroundings here. This Is It Fabulous Vermont Cabin W is another good place where you can hit pause. Book a couple of 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 CA $365 per night.
Can I find log cabins in Winchester?
If you're longing for a quieter pace of life, you'll discover it at one of our log cabins in Winchester. For example, Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Spend your days here snow shoeing and tubing and then return home to its many comforts. Time also seems to go slower at Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet. When you're in the mood to explore beyond your cozy digs, snow shoeing and canoeing opportunities are close by.
What are the highest-rated cabins in Winchester?
There are some properties that are hard to fault. Cabin: Private Hot Tub, Walk To Pats Peak Ski Area is a great example. With such an impressive rating, it comes with handy amenities like a patio and a fireplace. Another excellent option is Brook Road Cabin. A barbecue grill and a kitchen are a couple of the conveniences you'll appreciate here.
Why should I book a cabin in Winchester?
Affordability, rustic charm, nature-filled surroundings — there are loads of reasons for you to choose a Winchester cabin. Leave behind the noise of the concrete jungle and rise with the sound of songbirds and wildlife. There's ample adventure just around the corner too. Whether you're on vacation with family members, friends or your partner, you'll locate the ideal cabin on Expedia.
What are the top nature cabins in Winchester?
Our nature cabins in Winchester come in plenty of styles, shapes and budgets, but there's one thing they have in common — excellent access to the great outdoors. Warm And Inviting Jamaica Cabin W is a magnet for nature buffs. Amenities such as a fireplace and a firepit only make it better. Whether you want to slip your feet into hiking boots or just put them up, you can do it at Cabin - Beautiful Mt Area With Beautiful Scenic Views. Another top pick, it offers a patio and a barbecue grill.
What are some of the best cabins near Vermont Country Store in Winchester?
Cabin - Charming Fully Renovated One - Room Schoolhouse On 22+ Acres is one of the most popular cabins in Vermont Country Store. Thoughtful amenities, a beautiful backdrop and activities such as ice skating nearby and hiking make it the perfect escape. Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment is another place where nature and adventure combine. Settle in here and add nearby motor boating and a tennis court to your to-do list.

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