
House holiday rentals in Bennington County
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Top-rated house rentals in Bennington County
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Popular amenities for house rentals in Bennington County
House rentals with a pool

Hot Tub, Game Room, Minutes to Mt. Snow & Stratton
We had a great vacation at Whitley’s Airbnb. The house was very clean, spacious, and provided lots to do. It was also great being so close to Mt. Snow. I highly recommend this house and would love to come back!

Private chalet tucked in the green mountains
We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.

Modern 4BR Cabin, Near Lake & Mt. Snow
Host is extremely responsive, friendly, and accommodating. The house is well equipped with many kitchen supplies, including spices and other cooking products. The home is cozy and host equipped home with necessary items needed for a stay in the winter, such as sufficient salt, sand, shovels, and flashlight. the amenities of the chimney hill clubhouse are very family friendly as well. These include an indoor pool, hot tub, ping-pong, table, arcade, and indoor movie theater. Overall, a lovely home for a family and fantastic host.

Family/Dog Friendly Mountain Home w/ Amenities
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.

4bed, 2bath @ Chimney Hill w/Hot Tub & EV Charger
Lovely home. Hopefully I can stay here next year.

The Lodge, a 70's Getaway w/swimming pool
If you are reading this review.. BOOK this place right now. I have stayed in over 50 AirBnB’s across the US and this one stands out on another level. The attention to detail in every corner. The cleanliness. The amazing hospitality with the host walking us around the entire place giving us a tour. All the games blankets full bar and kitchen utensils were an amazing touch. I would easily go back. Loved this cabin so much it was home away from home. Did a small friend’s gathering for New Year’s Eve we spent 4 days here and didn’t want to leave. I’m telling you, if you see this review just book it. There isn’t a better option.

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!

Wander In | Close to Mount Snow & Stratton
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.
Weekly house rentals

Charming Vermont Retreat
Catherine’s place was perfect for our stay. It was so cute, nicely decorated, very clean, and convenient to everything. If we are ever needing a place to stay in Dorset we will definitely be back!

Vermont Village Retreat Near Mount Snow
Matt's Airbnb was a wonderful place for us to get away for a long weekend! The house was lovely with all the comforts of home. We loved so much about this house, especially the layout. All one floor, which was great! The mudroom was great for bags and boots, the kitchen was well stocked , and the living room was amazing- very comfy large sectional sofa for relaxing, a nice cozy little sun room to hang out on and read a book. Having 3 bedrooms and 2 baths were the perfect size, and the washer and dryer were an added bonus. We loved the outdoor space for grilling and walking our pups. Very peaceful neighborhood and wonderful little town with great restaurants! Matt was so nice and helpful with any questions that we had, and even offered us a later check out which was nice! We loved this part of VT and hope to visit again soon! Thank you Matt for being such a great host! We can't wait to book our next stay!

Stratton; 8 min! Swimming, 2 min. Pet friendly
Kelly was very responsive and helpful. She went out of her way to get us a last minute booking and it didn’t disappoint! It was clean, well stocked and very comfortable! I will definitely book this again when its available!!!

Comfortable Entire Farmhouse close to North Adams
We had a lovely time at Maura’s house! Maura was friendly and responsive and clearly loves to share this beautiful area with guests. The house was spacious and well kept. (I would note for those who might mind that there were some family photos, magnets, etc. up, but that didn’t bother us at all!) The house is about 10 minutes from Mass MOCA and less than 20 minutes to Williams College.

Waterfront Home on the Battenkill River
Andrew’s cottage was a delight to stay in. It has a well equipped and modern kitchen with dishwasher, and is very well supplied with pots, pans, coffeemaker, tea kettle, and all kinds of miscellaneous kitchen equipment. The bedrooms are comfortable and spacious, and the common space is also comfortable, roomy and nicely decorated. The cabin is located by the river, and looks out on green space, trees, birds and mountains. Andrew is a delight and was always accessible if needed, since he lives nearby. We recommend it highly. Henry & Ann

Cozy Condo near Mt Snow
My family and I had a great stay at John’s place. It was just as described and in a perfect location, located just a few minutes from Mount Snow and surrounded by all of the great restaurants that West Dover has to offer. The space was spotlessly clean and super comfortable to relax after a long day of skiing. John was very communicative and friendly and even left some treats for us upon arrival which was much appreciated. This might be our new top pick of places to stay when we are in the area!

The Village Cottage
Jason is incredibly accommodating. We've been visiting for two years now and absolutely love everything—the location, the easy access to town, and the place is so warm definitely a plus to have your own fireplace after ski the whole day. We can’t wait to come back!

VT at its best! - near museums & trails
This home was incredibly comfortable and spacious and was a perfect spot for our family’s stay for our daughter’s college graduation! Our favorite spot was the screened in porch! The kitchen is well stocked and the beds and linens were terrific. All of the pictures accurately portrayed the home and the two separate seating areas came in handy when I needed to work. Courtney also provided detailed instructions - such as WiFi passwords and restaurant recommendations etc. She was also extremely accommodating when I needed to add a night and check out a bit later than normal! Access was also very easy to the home with a keypad lock. I highly recommend this property and hope to stay again if we make it back to the area!
Private house rentals

Sunrise Surprise, spacious, great for entertaining
Wonderful stay, large spacious air bnb. Very clean, very comfortable felt right at home. Fenced in backyard, and local to many shops and restaurants. Would book again!

Peaceful Retreat near Unique Animal Encounter
Daniel's place was the perfect home base for our Berkshires getaway. We visited Mass MoCA and loved coming back to this quiet, peaceful retreat. The backyard was especially serene, I enjoyed my morning coffee outside and relaxing by the fire at night. One of my favorite parts was cracking the window open and falling asleep to the soothing sound of the brook out back, pure magic. Daniel was a gracious host, friendly, responsive, and thoughtful. The local charm added so much to the experience, including camels and other farm animals across the street, Farmer Dave is a gem. We'd happily stay here again!

Enjoy Summer & Private, Peace and Relaxation
This was our 2nd time stay at Delia’s place. Everything was as described and clean. Great spot and will stay again.

Memes High Mountain Lake House
We had a wonderful stay! We were able to snowmobile right from the house and enjoy the scenic views of the lake.

Home in the Heart of Dorset Village
Absolutely beautiful home inside and out. Very easy to find and within walking distance to the shops in Dorset. Plenty of private parking and easy access. We felt at home as soon as we walked in the front door. The entire home from kitchen, bathrooms and living areas were spotless and well stocked. We enjoyed all the light from the windows and the fantastic view of the pond out back. The bed and linens were superb. We were traveling with our two dogs and it was very convenient for them and we enjoyed their company during our travels. Our friends in nearby Manchester agreed that we found the "perfect" spot to stay in the area. Michael the host, was super friendly, communicative and helpful with his recommendations. Hands down our favorite Airbnb and are already trying to plan our next trip.

Cozy mountain getaway between Mt. Snow&Stratton
Even better than the pictures. It was a great place for a ski trip. I enjoyed walking around the house and exploring the property. For the price you can’t beat it. I would definitely recommend staying here if you are looking for a place.

Modern Farmhouse Retreat
Unfortunately we could only spend two nights here. We loved the spaciousness of the downstairs. It was great to be able to walk our dog nearby. Williamstown and Bennington are very close. I loved hearing the rain on the roof the first night. The birds were amazing. We loved our experience here!

Quaint Pink House on The Battenkill River
Beautiful home on the river. We enjoyed the back patio which overlooks the river. The house is charming and great location!
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Canterbury Farm