
Vacation rentals with a patio in Bennington
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Top-rated accommodations with an outdoor patio in Bennington
Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Arnies Adorable tiny cabin @ Green Acres
Relax at this unique and tranquil getaway. Tiny cozy cabin (2x12) Open concept Glamping tent on property Fits 3 perfectly, Twin bed enclosed/curtains twin futon and large Chair that opens up to a twin bed SHARED BATH HOUSE Summer months we have an outdoor shower which is attached to the outside of the cabin, outside near the cabin powered by generator- small fridge, lights, Keurig, & outlets /Hotplate gas grill firepit/ kindlin /newspaper/firewood provided dishes, glasses, mugs, silverware,

Peaceful VT Chalet w/ Mountain View’s
My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Cozy Hilltown Cottage
Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

The Birchwood Cabin - Stunning Mountain Views
Welcome to the Birchwood Cabin - a beautiful log cabin with stunning mountain views! Relax in the hot tub overlooking the mountains or enjoy hot chocolate by the fire. Play a game of pool or shuffleboard downstairs. The Birchwood Cabin is in a peaceful, quiet location but is only a 10-minute drive to Manchester, if you'd like to go shopping or grab a bite to eat! Hit the slopes at Bromley Mountain or Stratton Mountain or in the warmer weather head to The Equinox for a round of golf!

Serene & Stylet Chalet•HOT TUB•Skiing•Manchester
Hey there, relaxation enthusiasts and adventure seekers alike! Shady Pines Chalet is your spot: a groovy 4-bed/2-bath cabin tucked away in the lush, serene embrace of the Green Mountains! It's just 15mins from Manchester, where you can shop and dine like a pro. Plus, you're in prime adventure territory: hiking, kayaking, & fly-fishing are all on the menu. And if you're a winter warrior, Bromley (25min) and Stratton & Magic Mountains (40min) are ready for your skiing prowess!

1 bedroom guest house on dead-end rd
Enjoy a peaceful and private space with 1 bedroom, 1 bath, full kitchen and on site parking. Last house on a dead end rd. 5 min from Southwestern VT Medical Center. 40 min from Mount Snow. 25 min from MassMoca. 15 min walk to Main St where you can enjoy great food and shops. No smoking on premises. Please note there is stairs separating the bedroom (downstairs) and living area, bathroom, and kitchen (upstairs). The stairs are steep and may be difficult for some people.

Rustically Romantic Cabin Near Sweet Pond
COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES

Pumpkin Pine Cottage: your next adventure awaits!
Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Near Saratoga – King Bed, Tub, Fire Pit & Movies
Escape to this family-friendly Clifton Park retreat—just 20 mins to Saratoga Springs and 25 to Albany. Perfect for fall getaways with a fire pit, outdoor movie screen, private playground, basketball court, and garden. Features a king bedroom, home office, full kitchen, fast Wi-Fi, soaking tub, and 20' x 55' parking for RVs or boats. Relax in the crisp autumn air, enjoy backyard movie nights, and stay productive or cozy in a quiet, peaceful neighborhood.

Artistic Nature Cottage
Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!
Popular amenities for Bennington accommodations with an outdoor patio
Apartment rentals with a patio

Cozy two bedroom near Manchester

Vermont Ski/Okemo/Killington/Pico/Stratton/Bromley

Historic Victorian - Entire 3rd floor

Suite 23 - Spacious Sunny 2-BR with Mountain view

River View apartment

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

Spacious apartment close to skiing and rafting

Cozy Adirondack apartment
House rentals with an outdoor patio

Red Country Escape | Mountain Views

Enjoy Summer & Private, Peace and Relaxation

Charming Brookside Artisan Home

Foliage Ready! Play Area, Crib, 11 Acre Farmhouse

Contemporary Ascutney Cabin near Ski Areas

Birdie's Nest Guesthouse

Contemporary, Warm & Cozy Home mins to Saratoga

Tranquil mid-century modern Berkshires retreat
Condo rentals with a patio

Main St Escape | Explore Downtown Ludlow

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Slopes N Seasons | Trailside Condo at Mount Snow

Ski On/Off 2BR w/Pool, Fireplace & Arcade

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Seasons Condo on mtn-sports center-pool-Ski in-out

Luxury Condo*3BD3BA*Walk/Shuttle to lift

Lovely 1-Bedroom condo with indoor fireplace!
When is the best time to visit Bennington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $158 CAD | $189 CAD | $183 CAD | $158 CAD | $165 CAD | $208 CAD | $200 CAD | $203 CAD | $233 CAD | $186 CAD | $191 CAD | $175 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 a patio in Bennington

Total vacation rentals
Explore 10 vacation rentals in Bennington

Nightly prices starting at
Bennington vacation rentals start at $138 CAD per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Bennington vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Bennington rentals

4.9 Average rating
Bennington stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Saratoga Spa State Park
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Albany Center Gallery
- Bromley Mountain Ski Resort
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Berkshire Botanical Garden
- Dorset Field Club




