Vacation rentals with outdoor seating in Hancock

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Top-rated accommodations with outdoor seating in Hancock

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Top guest favourite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
5 out of 5 average rating, 123 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Top guest favourite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 465 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favourite
An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Farm stay in New Lebanon
4.95 out of 5 average rating, 262 reviews

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Top guest favourite
Tiny homes in Wilmington
4.99 out of 5 average rating, 362 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favourite
A peaceful scene reveals a winding road leading through a residential area with well-maintained homes. Snow-covered mountain slopes are visible in the background, flanked by trees that display early signs of changing seasons.
Townhouse in Hancock
4.93 out of 5 average rating, 107 reviews

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Guest favourite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield
4.95 out of 5 average rating, 210 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Guest favourite
An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.
Guest suite in Hancock
4.82 out of 5 average rating, 202 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Top guest favourite
Home in Lee
4.99 out of 5 average rating, 306 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Guest favourite
A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.
Townhouse in Hancock
4.84 out of 5 average rating, 100 reviews

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Top guest favourite
A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.
Tiny homes in Chatham
4.99 out of 5 average rating, 342 reviews

Boutique TINY home+private HOT TUB-walk to Main St

March-April midweek special: Bottle of prosecco, robes/slippers, s'mores. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful & private oasis, yet just a 2-min walk to Chatham’s Main St. lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis @artparkhomes.

Top guest favourite
A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.
Farm stay in Pittsfield
4.99 out of 5 average rating, 294 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Top guest favourite
An elevated deck is softly illuminated by hanging lights, featuring a hot tub and a panoramic barrel sauna. Snow covers the ground, and the landscape is filled with distant hills under a twilight sky, creating a serene outdoor retreat.
Cottage in Shaftsbury
4.98 out of 5 average rating, 760 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Popular amenities for Hancock outdoor seating rentals

When is the best time to visit Hancock?

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Avg. price$413 CAD$409 CAD$371 CAD$307 CAD$380 CAD$388 CAD$379 CAD$388 CAD$319 CAD$341 CAD$307 CAD$409 CAD
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Quick stats about vacation rentals with outdoor seating in Hancock

  • Total vacation rentals

    Explore 80 vacation rentals in Hancock

  • Nightly prices starting at

    Hancock vacation rentals start at $68 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 of Hancock vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hancock rentals

  • 4.9 Average rating

    Hancock stays are highly rated by guests—averaging 4.9 out of 5!

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