Pet-friendly holiday rentals in Bennington

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Bennington

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Averill Park

4.95 out of 5 average rating, 136 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Guest favourite

Tiny home in Clarendon

4.9 out of 5 average rating, 225 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favourite

Flat in Saratoga Springs

4.93 out of 5 average rating, 146 reviews

Cozy, Romantic, Historic Saratoga Apartment

Location, location, location! Close to it all! Less than a 5 minute walk to all the best of Saratoga's restaurants and dining, nightlife, and family-friendly activities. walking distance to the track, two blocks to downtown, museums, shopping, parks, and movies. Trolley and bus goright past the house to SPAC, golf, Racino, etc. My place is great for couples, solo adventurers, and furry friends (pet $15/night with prior approval, ). Fantastic weekend spot! Can accommodate up to 3 people.

Top guest favourite

Chalet in Dover

4.98 out of 5 average rating, 109 reviews

Mountain Chalet: Brook-Hot Tub-Firepit-Mins to Ski

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best cuisine VT has to offer.

Guest favourite

Guest suite in Charlemont

4.91 out of 5 average rating, 206 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Guest favourite

Home in Peru

4.91 out of 5 average rating, 162 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Comfortably accommodates 12 people. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Guest favourite

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favourite

Flat in Corinth

4.8 out of 5 average rating, 131 reviews

Adirondack Penthouse, Sleeps 10. Steps from Beach.

Our LARGE apartment overlooks Main Street of our quaint village. See the sparkling waters of the beautiful Upper Hudson River Beach across the street. 15 mins to SARATOGA or Lake George. Sleeping: a Queen & a Full bed in Main bedrm, a Pull-curtain room separator, # 1 cot available. 2nd bdrm: 2 full size beds. Room Separator Curtain. Sofa Sleeper in the Living Room. Balcony off main bdrm. Full kitchen, dining room. *ALL surfaces sanitized/Disinfected. Streaming TV.

Guest favourite

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 122 reviews

Magic Forest Farm’s Purple Palace

Our slice of paradise consists of 225 acres of forested land nestled in the foothills of the Catskills near Albany. We are a homestead and small community devoted to the principles of organic farming and self reliance. We grow much of our own food and forage many types of wild mushrooms. You will be sure to enjoy the spectacular mountain views, friendly farm animals, and secluded trails. The house is spacious and decorated with landscape oil paintings.

Guest favourite

Cottage in Lanesborough

4.84 out of 5 average rating, 278 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016) CURRENTLY BEING UPDATED and RENOVATED, (March and April 2025!) private cottage 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. For conditions message Jill.

Top guest favourite

Cabin in Lake George

4.99 out of 5 average rating, 121 reviews

Pet friendly,private, perfect Lake George location

Grizzly Bear Lodge is situated on a conveniently located, private, 2.5 acre lot that is just a 3 minute drive to Lake George Village. Our guests love that they don’t have to sacrifice privacy and seclusion to be minutes from everything that the Lake George area has to offer. Close to the village, Bolton Landing, Lake George outlets, hiking, skiing, snowmobile trails, and all amenities! We are pet and family friendly!

Superhost

Tiny home in Nassau

4.94 out of 5 average rating, 142 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays are welcome! *** IMPORTANT *** Our photos previously showed screens enclosing the porch, but we have removed them due to wear from pets. Maintaining a pet-friendly environment is important to us, so the screens are no longer part of the tiny house. Enjoy a stay in our clean, charming, unique tiny home. This waterfront property features a private peninsula with a sandy entrance to the water.