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Featured Cabins in Winchester

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

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Book a stay at this family-friendly cabin in West Halifax. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Honora Winery and Jacksonville Pond are located nearby.
Kitchen
Washer
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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Stay at this cabin in Vernon. Enjoy a garden, laundry facilities, and hiking/biking on site. Popular attractions Norcross Wildlife Sanctuary and Satan's Kingdom Wildlife Management Area are located nearby.
Kitchen
Washer
Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views

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Book a stay at this family-friendly cabin in Jacksonville. Enjoy a garden, laundry facilities, and patios. Popular attractions Honora Winery and Jacksonville Pond are located nearby.
Kitchen
Washer
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

The price is CA $163 per night
CA $163
CA $276 total
Jul 23 - Jul 24
includes taxes & fees
Stay at this cabin in Fitzwilliam. Enjoy free WiFi, a sauna, and a garden. Popular attractions Fitzwilliam Library and Rhododendron State Park are located nearby.
Kitchen
Free WiFi
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

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Stay at this cabin in Townshend. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Townshend State Park and Townshend State Forest are located nearby.
Kitchen
Washer
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

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Stay at this cabin in Rindge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cathedral of the Pines and Fosket Wildlife Refuge are located nearby.
Kitchen
Washer
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

The price is CA $866 per night
CA $866
CA $1,860 total
Aug 11 - Aug 12
includes taxes & fees
Book a stay at this family-friendly cabin in Wilmington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions The Art of Humor Gallery and Molly Stark State Park are located nearby.
Hot tub
Kitchen
Cozy Log Cabin - Dog Friendly

Cozy Log Cabin - Dog Friendly

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Stay at this cabin in West Halifax. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Honora Winery and Jacksonville Pond are located nearby.
Kitchen
Pet-friendly
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

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Stay at this cabin in Jacksonville. Enjoy free WiFi, 2 outdoor pickleball courts, and a garden. Popular attractions H.O. Cook State Forest and West Branch Wildlife Sanctuary are located nearby.
Hot tub
Kitchen
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

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Stay at this cabin in Wilmington. Enjoy laundry facilities, patios, and Netflix. Popular attractions Lake Raponda and The Art of Humor Gallery are located nearby.
Kitchen
Washer
Cozy Log Cabin on the River | Fireplace | Loft

Cozy Log Cabin on the River | Fireplace | Loft

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Stay at this cabin in Townshend. Enjoy a garden, laundry facilities, and balconies. Popular attractions Townshend State Park and Townshend State Forest are located nearby.
Kitchen
Washer
Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!

2 out of 5
The price is CA $174 per night
CA $174
CA $335 total
Jul 29 - Jul 30
includes taxes & fees
Stay at this cabin in Newfane. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Rock River Preserve and Manitou are located nearby.
Free WiFi
Gym
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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.

Top trending hotels in Winchester

The Colonial Hotel

The Colonial Hotel

625 Betty Spring Road, Gardner, MA
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8.6/10 Excellent! (1,004 reviews)

Winchester Cabin Rentals

Does the thought of waking up in a plush bed, stepping out onto a private patio, and taking in views of the lovely surroundings sound like exactly what the wise wanderer ordered? Then it might be time to peruse cabin rentals in Winchester. Whether you’re looking for a log cabin to host your weekend of solitude, or are curious about one of many luxury cabin rentals to host you and your special someone, Travelocity has everything you need for your next vacation.

Travelers have always appreciated Winchester for its natural wonders, and now you can too. Spend your days exploring all the area has to offer, from its scenic trails near your accommodation to quirky boutiques and delicious restaurants in town. Wake up early for a sunrise hike, go fishing at a nearby lake, or sleep in and find a shady tree to read under in the afternoon. There’s no right or wrong way to experience the outdoors, but there are tons of cabin rentals that will let you enjoy them more thoroughly.

Even if your plans include roughing it while you’re out hiking during the day, you don’t need to shy away from enjoying the many amenities available at cabins in Winchester. Reserve a cabin with a spa tub for ultimate relaxation, or book one of many appealing cheap cabins that’s located near breweries and restaurants.

Confirm your hunch—that Winchester is the perfect place for your next getaway. Reserve a cabin with Travelocity, and get ready to explore the area to your heart’s content. Nature’s calling, and the best way to answer it is from inside an inviting cabin.

Winchester Cabins essential information

Accommodation
34 Cabins
Lowest Price
CA $135
Highest Price
CA $866
Popular accommodation
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist, Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, Jacksonville Cabin w/ Wraparound Deck & Views, Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna, Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT, Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!, Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow, Cozy Log Cabin - Dog Friendly, This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views! , Charming Wilmington Cabin, 8 Mi. to Mt Snow!, Cozy Log Cabin on the River | Fireplace | Loft, Wellness Getaway with a Personal Sauna, and Private River Beach!

Frequently asked questions

What is the price range for cabins near Winchester?
Awaken to the sounds of nature in one of our cabins near Winchester, priced between CA $135 and CA $866 a night. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How cheap are cabins near Winchester?
Find a cabin rental in or near Winchester that matches your taste from as little as CA $135 a night. This was the lowest rate available in the last seven days. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many options are there for Winchester cabin rentals?
With 262 lodging options to reserve in and around Winchester, Travelocity makes it easy to organize an exciting getaway. More than your stock-standard hotel experience, places like Private And Artistic Cabin, Pet Friendly and Cabin - Cozy Chalet, Lake Pauline, Lake Rescue offer a cozy stay with plenty of charm.
What is there to do when renting a cabin near Winchester?
Spend your days chasing adventure when you stay in one of our Winchester cabins. Combining the appeal of camping with creature comforts, cheap cabin rentals are the ideal base for your next family getaway.

  • Leading the list of family attractions to enjoy is Quechee Gorge Bridge. From Winchester, it's around 153 kilometers away to the north and a wonderful spot to spend time together.
  • Round up the troops and make your way to Tower Hill Botanic Garden. This sight is about 113 kilometers to the southeast of Winchester.
  • Lastly, Equinox Preservation Trust is around 113 kilometers to the northwest of Winchester. It's an excellent place to keep the troops entertained and make new family memories along the way.

What are some Winchester mountain cabins?
There's nothing quite like a stay in the mountains to leave you feeling refreshed and on top of the world. Take in picturesque landscapes and enjoy some downtime at one of these Winchester mountain cabins:


What are some river cabins near Winchester?
Wake up in the mornings to water views and the sound of tweeting birds when you stay at one of these river cabins near Winchester. From cozy rustic retreats to large luxury cabins right on the riverfront, we know you'll find one that's right for you.


What are some Winchester cabins with pools?
If you want to create a splash on your next vacation, lock in a Winchester cabin with a pool. Spend every day enjoying the water at one of these awesome options:


What are the best Winchester beach cabin rentals?
Cool off in the water, go for a stroll along the shoreline and enjoy beautiful ocean views. There are lots of terrific seaside experiences to be had when you stay at one of these Winchester beach cabins:

  • Toss your beach bag down and get comfortable at Cabin - Relax, Reconnect And Enjoy. As well as a host of other convenient amenities, it offers on-site watersports and children's activities.
  • It won't take you very long to see why Cabin - Lakefront - King - Petsok - W And D is also popular with beach-loving travellers. Convenient amenities here include on-site watersports and clothes washing facilities.

How can I find a great cabin near Winchester on Travelocity?
Browse Travelocity's amazing selection of cabins by price, amenities and location using our handy filter tool. Whether you're after a Winchester family cabin with space for a small army or a comfy lodge for just the two of you, we'll help you find your perfect match. If you're concerned about changing plans, select a property that offers free cancellation.