
Vacation rentals with outdoor seating in Hancock
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Hancock
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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

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!

The House of Pi
Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

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.

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!

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.

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.

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.

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.

Wildlife Lakeside Cottage; views/wildlife
Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

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.

Cute Cozy Comfy Cottage in the Berkshires
A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs at $100 per dog. My cottage sits on 13 privately owned acres. Partially fenced in 3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!
Popular amenities for Hancock outdoor seating rentals
House rentals with outdoor seating

Escape to Lakefront Leisure—Amazing views!

Family-friendly historic charm w/ modern amenities

The Gate House--Experience Vermont!

Modern Barn on 12 acres w Sauna, FirePit+swimming

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Chic Hudson Farmhouse w/ Fireplace & Porch

19th c. Barn in The Berkshires

Cozy, peaceful lake house close to Jiminy Peak
Apartment rentals with outdoor seating

Sunny, light filled loft in 1873 Colonial

Bennett Abode

Suite 23 - Spacious Sunny 2-BR with Mountain view

The Beer Diviner Brewery Apartment

Hudson River Beach House

Modern Copake Falls Getaway - 8 Mins to Catamount

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Enjoy every season the Berkshires have to offer.
Condo rentals with outdoor seating

3BR Golf course condo w/ views & close to skiing

Waterfront Apartment Near Saratoga

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Historic Gem, Fireplace,2BR/2BA,Capitol District

Spacious 3 bedroom apt in Lenox historic downtown

Quiet refuge in Great Barrington

10th Hole Haystack Golf Course in Wilmington VT

Berkshires Getaway < 1 Mi Skiing & Hiking!
When is the best time to visit Hancock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | -5 °C | -4 °C | 1 °C | 8 °C | 14 °C | 18 °C | 21 °C | 20 °C | 16 °C | 9 °C | 4 °C | -2 °C |
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!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- House rentals Hancock
- Ski-in/ski-out rentals Hancock
- Rentals with an EV charger Hancock
- Cottage rentals Hancock
- Hotel rooms Hancock
- Apartment rentals Hancock
- Rentals with a hot tub Hancock
- Rentals with pools Hancock
- Rentals with a patio Hancock
- Family-friendly rentals Hancock
- Rentals with a firepit Hancock
- Rentals with a fireplace Hancock
- Pet-friendly rentals Hancock
- Condo rentals Hancock
- Rentals with a washer and dryer Hancock
- Rentals with a sauna Hancock
- Fitness-friendly rentals Hancock
- Rentals with outdoor seating Berkshire County
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Taconic State Park
- Mohawk Mountain Ski Area
- Saratoga Spa State Park
- June Farms
- Ski Sundown
- Hildene, The Lincoln Family Home
- Norman Rockwell Museum
- Naumkeag
- National Museum of Racing and Hall of Fame
- Opus 40
- Berkshire Botanical Garden
- Hancock Shaker Village




