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.

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Guest favourite

Cabin in Warrensburg

5.0 out of 5 average rating, 157 reviews

Romantic Lake George Getaway~Chickadee Hill

*Romantic getaway nestled in the Adirondack Mountains, just 15 minutes to Lake George *Vintage Record Player, Farm Fresh Eggs and pollinator gardens *A dreamy escape into nature where you will wake up and feel like you are still dreaming *This is not just any five star stay step outside we have millions our night sky is breathtaking *We strive for our guests to have nothing less than a five star experience, as you can see by our reviews Chickadee is decorated for Christmas Nov 1st-January

Dec. 19 – 26

$241 CAD per night

Guest favourite

Cabin in Tannersville

4.99 out of 5 average rating, 145 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Aug. 24 – 31

$220 CAD per night

Guest favourite

Condo in Killington

4.95 out of 5 average rating, 130 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

May 1 – 8

$168 CAD per night

Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 119 reviews

Mi Casa es su Casa!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K TV, surround sound system. Wi-Fi access. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage. Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Jul. 27 – Aug. 3

$173 CAD per night

Guest favourite

Apartment in Bennington

4.8 out of 5 average rating, 35 reviews

North Bennington, VT conveniently located unit.

Fully furnished ground level unit includes heat, AC, Wi-Fi, cable TV, snow removal, garbage removal, parking & spacious backyard with patio & fire pit. Kayak on site, lake less than half mile away. Historical area, closely located near Bennington College, several walking trails, nearby lakes & skiing, quaint No Bennington town with library, restaurants, laundromat, gas station, variety stores, Park McCullough Mansion, movie theatre, grocery stores, banks & more all within half to one mile.

Jan. 8 – 15

$178 CAD per night

Guest favourite

Place to stay in North Adams

4.93 out of 5 average rating, 114 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

May 8 – 15

$572 CAD per night

Guest favourite

Apartment in Albany

4.99 out of 5 average rating, 150 reviews

Beautiful Center Square Garden-Level Unit

This completely modernized garden-level space provides a charming and unique atmosphere while also being centrally located in the Capital Region of New York. My partner and I have taken ample time to carefully craft this space to maximize its potential and ensure your enjoyment. Featuring a fully loaded kitchen with stainless steal appliances, marble countertops, exposed brick throughout, tasteful decor, and your own private patio. We truly hope you enjoy this space as much as we do!

Jan. 12 – 19

$164 CAD per night

Guest favourite

Cabin in Londonderry

4.96 out of 5 average rating, 100 reviews

Summit view cottage: Secluded cabin with hot tub

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 6 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn. Very close proximity to the town of Manchester, which has great shops and restaurants.

Apr. 1 – 8

$662 CAD per night

Guest favourite

Cottage in Newfane

4.99 out of 5 average rating, 176 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Aug. 17 – 24

$242 CAD per night

Guest favourite

Cottage in Orange

4.94 out of 5 average rating, 131 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Jan. 19 – 26

$207 CAD per night

Guest favourite

Apartment in Schenectady

4.9 out of 5 average rating, 176 reviews

Bring your Kayak or paddleboard this Summer!

If these walls could talk, they'd tell a story of the history of Glenville, NY! Starting as a Broom Corn Farm and then a Speakeasy during Prohibition, the original bar is located in the basement! This renovated New England-style colonial has beautifully landscaped grounds and butts up to the Mohawk River, providing privacy and views. Walking the property not only gives you a bit of exercise but allows you to take in the beautiful views and native foliage.

Dec. 3 – 10

$166 CAD per night

Guest favourite

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 125 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

Dec. 19 – 26

$144 CAD per night