
Pet-friendly vacation rentals in Bennington
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Top-rated pet-friendly home rentals in Bennington
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Pet-friendly house rentals

Airy 5Br-2Ba,Kids Rm, 6TVs,Pvt Fence-yard&Parking!
Rashawn's place was great! Near downtown Albany, and plenty of sleeping space. Great for any size groups.

3br/2ba Family Friendly home- 1mi from the track!
Brooke's place is a good size...lots of room and so many nice touches (especially the abundant amenities provided for a small child). Very clean. Just as pictured. All good. The only thing I'd say as a bit of info to a prospective Airbnb-er, is that this location is not a walk to town spot, unless you consider 1.7 miles to the main shopping/dining area walkable. That said, it is still incredibly convenient...super quick drive to town or to race track or the lake...all while staying in a quiet, woodsy neighborhood setting.

Large Charming Home close to MassMoca
Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to be back!

Charming dog friendly home with private yard!
We enjoyed our stay. The house is very cozy and clean. The backyard was my favorite part, since we were travelling with our dog and he very much enjoyed freedom in the yard and a nice weather! The area is very peaceful and quiet.

Entire HOUSE Walk to ALL Dogs OK
Nancy’s place was a great option for my stay in the area. The kitchen had everything I needed, and the couch was comfortable. As was the one bed I slept in. I was visiting for a work trip. Nancy was also incredibly responsive to any questions I had, and was offering suggestions for the area I found useful. I’m glad to have found this place. While on this trip, I did not bring my dogs, I will be sure to stay here on my next one to the area. I typically stay in hotels here, but I will do my best to stay at Nancy’s anytime visiting in the future.

Modern Spacious Home with Mountain Views
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

Backstretch Getaway
Location, location, location! This is a quiet abode in walking distance to the horse track and downtown Saratoga Springs. The home owners were extremely accommodating, going so far as to overnight a coffee press that we mistakenly broke! How kind! The space was clean, the beds were comfortable, and we felt right at home! We would love to visit again.

3-bedroom house close to track, downtown, SPAC
we had such a great stay! short Uber ride right into downtown saratoga, and it's just minutes from SPAC. would definitely stay again!
Pet-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

The 1770 House
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!

Moon Valley Country Retreat no clean fee pets yes
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

Modern Barn on 12 acres w Sauna, FirePit+swimming
there was lots to do inside the house as well as outside. everything was amazing

Beautiful rustic woods and fields retreat.
This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!

Need a Getaway??
Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

Country Getaway Tiny House in Woods w/Pool/Sauna.
House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Private, pet-friendly home rentals

Cute Cool Cabin! Plymouth, Vermont.
Alecia and John were meticulous hosts from the well curated guide book to their responsiveness when we had questions. All made for a wonderful family fourth of july! We look forward to returning.

Little Red House Vermont
What an amazing place to visit Vermont. I had a great time at the little red house. The place is beautiful and quiet. It is a 12 min drive to Mount Snow. Joe has a bunch of classic DVDs and we enjoyed some of them during our stay. The place is very clean and there is warm water and WiFi.

2 Bedroom Cottage-Green Haven Resort-Lake George
Couldn’t recommend Green Haven anymore. Barbara and Gregory were fantastic hosts, were extremely hands on and accommodating to make it a perfect stay for my family and dog. Everything in the listing is described perfectly and the property and cabins are super clean. Location is fantastic as well, just a very short drive into Lake George village.

Lake George Getaway with SAUNA!
Ali was an amazing host! The location was great, about 5 minutes from the lake. Super cute place and we felt right at home. Check in was smooth and so was check out. She had clear communication and was extremely friendly and kind. I would definitely recommend staying here not only because of the location but just the warm cozy feeling of being at home and feeling valued by the host.

Hudson: MV Buren 2 bedroom cottage Lake Property
Everything was exactly as it was in the Description. It was a bit tricky finding the exact location reason being it was dark out when we arrived. However, Ann & Francois were great and responded quickly and stood on the phone with us and guided us until we arrived at the front door. all-inall it was a very pleasant stay and experience. We will definitely look forward to another visit. I recommend this place to all who enjoy these types of experiences.

Private cottage in the woods
We enjoyed our stay so much! The place was nice and clean and quiet, perfectly organised and thought through. Karen was a welcoming, friendly, and helpful host. I wish more AirBnBs were like this! Would be happy to return someday.

Sowilo Pine House. All-inclusive food and drinks.
Great place for a getaway in the mountains!Hunor and his family are very kind and accommodating. The tiny home was so nice and cozy, the views were amazing, the food was delicious, and the service was 10/10. There’s so much to do in the area and there are also great amenities at Sowilo. I would come again.

Quaint Suite in Center of Adams
Really great spot for a smaller group, has everything you need in one go. Great bed to sleep on too!
Quick stats about vacation rentals that are pet-friendly in Bennington
Total rentals
10 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
490 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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