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Featured Cabins in Winchester

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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.

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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
21 Cabins
Lowest Price
CA $100
Highest Price
CA $219
Popular accommodation
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!, Rustic Retreat: Cozy Log Cabin, Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, Cozy Log Cabin on the River | Fireplace | Loft, Peaceful Cabin in the Woods and near the mountains, Jacksonville Cabin w/ Wraparound Deck & Views, Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT, Cozy Falls Brook Cabin: Hike & Swim On-Site!, Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist, Mountain Top Escape, Cabin Retreat in Southern Vermont, Cozy Updated Log Cabin with Mountain Views close to Monadnock

Frequently asked questions

What is the price range for cabins near Winchester?
Beat a retreat from the concrete jungle and stay at one of our popular cabins near Winchester. Priced from CA $100 to CA $219 per night, they’re the perfect blend of creature comforts and nature. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How cheap are cabins near Winchester?
Act quick. The cheapest Winchester cabin retreat in the last seven days was just CA $100 a night. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many options are there for Winchester cabin rentals?
There are 188 options here. If you need a comfy retreat away from the daily rat race, a Winchester cabin rental is guaranteed to please. Cabin - Cozy Hideaway Near Ludlow/okemo. Hot Tub and September Special 15% Off Mid Week Bookings At The Secluded Trout Cabin are two superb choices.
What is there to do when renting a cabin near Winchester?
Spend your days searching for adventure when you reserve one of our Winchester cabins. Combining nature with modern comforts, cheap cabin rentals are the ideal base for your family getaway.

  • Buckle up and make your first stop Quechee Gorge Bridge. It’s around 97 kilometers north of Winchester and appeals to plenty of younger travelers (as well as their parents!).
  • Mount Greylock, about 64 kilometers to the west of Winchester, is another exciting day trip outing. Charge up your camera and capture a beautiful family photo together.
  • If you’re on the road with the kids, don’t forget to visit Tower Hill Botanic Garden. It’s around 72 kilometers to the southeast of Winchester and a huge hit with families.

What are some Winchester mountain cabins?
When you’re eager to escape from the city and journey into nature, a Winchester mountain cabin is a great choice. Go on a hike, take in the clean, crisp mountain air and then unwind at one of these lodgings:


What are some cabins with hot tubs near Winchester?
There’s nothing as relaxing as a long, soothing soak. Take your escape to the next level and stay at one of these Winchester cabin rentals with a hot tub:


What are some great Winchester cabins?
Tucked away in nature but with many comforts of home, there’s nothing better than a cabin stay if you’d like to really experience the great outdoors. Leave the hustle and bustle behind at one of these popular Winchester cabins:


How can I find a great cabin near Winchester on Travelocity?
Locking in a terrific Winchester cabin is easy with Travelocity. Step 1: Enter your travel details. Step 2: Use our useful filter tool to tailor your results. Then just lock in your favorite stay and start counting the days! Think your plans could change? Choose a cabin that has free cancellation. Booking with Travelocity means booking with confidence. Find the same property cheaper elsewhere within 24 hours and we’ll refund you the difference. It’s our Price Guarantee.