Bennington has many things to do on offer, and if there’s one thing you have to know about the place, it’s not your usual American vacation haunt. The county is well known for its cheese trails, with more than 45 cheesemakers (and a fair share of award-winning cheesemakers) covering the vicinity. Sample cheese made from the milk of goat, cow, and even sheep while you explore its other sights, which include the amazing architectural work featured across the city, the Bennington Battle Monument, and the Old First Church. For booking comfy accommodations that are bound to give you the best in price and comfort while you’re away from home, continue reading to find out more about the top Airbnb vacation rentals in Bennington, Vermont.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 06, 2024.
1. The Old Academy
One of the best places to stay in Bennington, Vermont, this spacious house is nestled in the midst of lush greenery on the historic street of Monument Avenue. Bennington Battle Monument and the Old First Church are only a stone’s throw away.
The house was constructed in 1821 and has witnessed a carefully curated restoration over the past years to incorporate modern amenities while keeping its old-world charm intact. Best suited for families, the exquisite house features cosy beds for a restful night of sleep after a long day of exploration. A crib is also parked inside for toddlers.
Guests can stay toasty by the comforting embers of the fireplace and curl up with a book on chilly evenings. A high-speed internet connection coupled with a workspace ensures a smooth day of remote work if needed. A kitchen also awaits should you want to fix meals when hunger strikes.
Bennington, Vermont, United States
380 meters (0.3 ft) from Bennington Battle MonumentSuperhost
Accommodates: 6
Top guest reviews
Amenities & Room:
the beds were super comfythe waffle mix and iron were much appreciated as was the delicious vermont maple syrup he providedthe space is handsomely decorated and furnished with period antiques yet the kitchen is modern and well-equippedgreat spot right next to the monument beds were comfy and it worked great for two families with kidsthe beds were all comfortable and cozyCleanliness:
everything was cleanthe home was very clean and well furnishedhome was spacious well laid out perfectly appointed and spotlessHost:
james is a wonderful hostjames was a wonderful hostour host was very helpful and made us feel at homejames was a very thoughtful and accommodating hostjames was very communicative and helpfulRead more reviewsLocation:
the location is incredible - so close to historic sites and downtown easy access to the highwaythe location of the property is fantasticthe location was amazing located in a very well kept and manicured historic districtit is such a unique find and located perfectly in a historic walkable areait’s a great location and has everything you will need for your stay
2. The Octopus's Garden (from USD 84)
Found in Bennington, Vermont, this one-bedroom apartment is only a 15-minute walk from downtown, which is bustling with shops, art galleries, and restaurants. An ideal fit for two guests on a romantic getaway, this charming and cosy accommodation rests on the first floor.
You can unwind on the queen-sized bed and watch a movie or two on the high-definition TV that is equipped with Roku. A whirlpool tub also awaits should you fancy a relaxing soak right after.
Out in the beautiful backyard, enjoy soaking up the sun while sipping on a glass of wine with your partner. If you are craving good food during your stay here, you can head to the nearby Madison Brewing Company Pub & Restaurant for great spreads and drinks. Stop by Henry’s Market and pick up fresh meat for rustling up a flavourful meal in the equipped kitchen of the Airbnb.
Top guest reviews
Amenities & Room:
octopus’s garden is spacious meticulously cared for with amenities for a relaxing comfortable convenient overnightfrom the huge bathroom to the jacuzzi in the bedroom it's a very nice and cozy spaceno stove or burners but we could easily have breakfast and make sandwichesnice towels extras in the cabinets in the bathroom and a garbage and container for recyclablesthe shower was a little tight but very clean and well stocked with shampoo and conditioner and soapCleanliness:
very clean and i would definitely returnthe space was clean and matched the descriptionclean and perfect for a quick ski getawaysuper clean it's evident gail takes good care of her placewell appointed comfortable bed and bath spacious and cleanHost:
didn’t meet our host but everything was smooth and lovelygail was a wonderful host at the octopus gardena beautiful place and a nice hostthank you for hosting usgail and her daughter made us feel very welcome and were helpful with recommendationsRead more reviewsLocation:
beautiful place right in towngreat location when xc skiing at prospect mountainbeautiful area and place was located right in town and private entrance a pluswalking distance to restaurants gail was very responsivethis was a super easy booking the location was perfect walkable to town and restaurants
3. Spacious and spectacular master suite (from USD 195)
Located in Old Bennington, Vermont, this lodging comes with a queen-sized bed and a private bathroom. There are tons of outdoor sports to be explored, as well as the Bennington Battle Monument and Bennington Museum. You will be able to use the outdoor grill, screened porch, chef’s kitchen, and music room to entertain yourself. Other amenities include free WiFi and parking, heating, and a hot tub.
Top guest reviews
Amenities & Room:
this is a beautiful old house the room is large with a lovely view of the bennington monumentthis large master suite has glorious ambient light and comfortable furnishings(there was plenty of complimentary tea and coffee in the kitchenoh and i loved the ceiling fan that looked like a lee bontique designthe room was clean bright and airy with a view of the bennington monumentCleanliness:
the bathroom was large and it was all clean and tidyit was quiet and comfortable clean and beautifulthe bedroom and bath are well appointed clean comfortable and gorgeouswe had a nice stay the accomodation was very large and spaciousHost:
gorgeous home and very friendly hostkathy was attentive and helpful regarding our questions and she gave some great restaurant suggestionsthe hosts are great - very welcoming generous and helpfulthey were both very accommodating and helpful about our needs and i couldn’t ask for better hostsall in all this place and the hosts do not disappointRead more reviewsLocation:
the location is in a lovely neighborhoodit's a great location close to town but very privategreat location in a beautiful and historic townwonderful location for exploring benningtonkathy's place is in a perfect location for exploring bennington
4. Studio retreat (from USD 97)
This cheap Airbnb in Bennington is located between the skiing slopes on the southern end of Vermont and the cultural segments of North Adams and Williamstown. You’d be living in a modern basement apartment, which makes up part of a 1860s farmhouse. The unit has its own bed and bathroom, as well as a washer and a dryer, WiFi, heating and free parking. There is a kitchen you could use to make a meal for yourself. Do note that no pets are allowed.
Top guest reviews
Amenities & Room:
we loved the views and the amazing bathroomthe wifi was good when we needed ita comfortable modern apartment with lovely viewsthe view from the apartment is beautiful and the bathroom is very uniqueloved this place waterfall shower heated floors very privateCleanliness:
very clean and convenientspotless and super quietnice clean place to staythe place was sparkling clean and very cozypeaceful quiet clean and comfortable studio apartmentHost:
thank you barbara for being such a great hostvery warm host and lovely accomodationsbarbara is an outstanding hostbarbara is a lovely host with a wonderful bnb spaceshe was super friendly and made sure we had what we neededRead more reviewsLocation:
beautiful location overlooking the surrounding hillsthe location is absolutely beautiful and very peacefulbeautiful location warm and cozy spacethe studio is a great location between prospect mtbarbara's apartment was an ideal location for our trip to see vermont's fall color
5. Off-the-grid cabin in Vermont (from USD 180)
Located in Woodford, this wooden cabin can take in four guests at a time, with two bedrooms, a king-sized bed, a queen-sized bed, and a bathroom. You won’t be able to tear your gaze away from the unrestricted view of Vermont’s mountains, which are truly a sight to behold. Facilities are pretty basic here, with an outhouse that does not have a shower or running water. Showers are, however, available at the Bennington Recreational Center on Gage Street for 1 USD. You and your fellow guests will be able to use the TV, heating, complimentary parking and kitchen within the cabin area. A no-smoking rule applies.
Top guest reviews
Amenities & Room:
unbelievable views and super cozyviews were unreal showering down at the rec center was easy and quickcozy cabin with a gorgeous viewbeautiful cabin with picturesque views & generator that provides (if necessary) power for essentials very comfortable living spacegreat cozy cabin with enough amenities to be more than comfortableCleanliness:
out house was cleanalthough there is only an out house for a bathroom it was clean and privateeverything was nice and cozy clean easythe cabin was adorable clean and had wonderful viewsthe place was clean (especially the linen and bedrooms) but could be somewhat cleanerHost:
the owner is very responsive if you have any questionscarson was very responsive when we had questionsone can tell he is an absolutely amazing host as he went out of his way to helpcarson was very accommodating and helpfulcarson is very responsive if you have any questions during your stayRead more reviewsLocation:
the cabin and location are beautifulhope to return again also close to a cute friendly town with good eatscarson’s cabin is located in one of the best placesthe cabin is located in a beautiful and quiet spotamazing location will be coming back for sure
6. Bennington barn (from USD 150)
This spacious home can take in seven guests at one go and is made up of three bedrooms, four beds, and a bath. You will be able to easily access Vermont’s covered bridges and ski areas, as well as Bennington Center for the Arts and the Bennington Monument. The house comes with cable TV, WiFi, a washer and a dryer, breakfast and a travel crib. There is an indoor fireplace, a patio and a gas grill that is also made available to you. Do note that smoking and pets are not allowed.
Top guest reviews
Amenities & Room:
the three bedrooms had comfortable mattresses and high quality sheets and pillowsperfect location for exploring south vermont and the place itself was very homely and very comfortablethe shower was a delight - as was the large refrigerator well stocked with bottled watergood quality beds and bedding were much appreciatedat eleanor's we had plenty of room to spread out regroup and relaxCleanliness:
very nice clean convenient placeeleanor's place was warm clean and cozybeautiful cozy and spotless clean houseclean comfortable spacious and quietthe house was very cleanHost:
mike and eleanor were perfect hostsowners are super friendlyeleanor is also a wonderful host who is kind and responsiveeleanor & mike were very kind and welcomingeleanor and mike were terrific hostsRead more reviewsLocation:
great location comfortable bedslocation was perfect with grocery stores restaurants gas stations within 2 miles from the barnexcellent location right off the highwaycharming place and beautiful locationclose to highway and easy trip into sweet little nearby towns
7. The Nest
The Nest is an apartment that’s spacious enough for four people and made up of two beds and a bath. It’ll take you no more than a 10-minute walk to reach the local diners, shops, and museums. Within, there’s a comfy queen-sized bed and a couch for sleeping arrangements. Other facilities extended include WiFi, a washer and a dryer, air-conditioning, a TV and a kitchen. There are a couple of ski areas nearby, including Prospect Mountain and Jiminy Peak. Do note that this home is not suitable for children below the age of two years.
Bennington, Vermont, United States
2.15 km (1.4 mi) from Bennington Battle MonumentAccommodates: 2
Top guest reviews
Amenities & Room:
we especially enjoyed her book collection and all the positive vibes that emanate from the apartment" it was comfortable cozy and had all the amenities you could hope forwe enjoyed the tea and coffee and sitting at the sweet kitchen tablethe bonus of having some breakfast treats available (coffee tea fruit) made our mornings run more smoothlythis little apartment was perfect for a mother-daughter visit to bennington collegeCleanliness:
very clean and comfortableeverything was very cleaneverything was clean and in perfect orderit is clean and welcomingthe apartment was very clean and charmingHost:
lovely touches and hostgail is a wonderful hostgail is a great hostgail was a super responsive hostthanks gail for being such a great hostRead more reviewsLocation:
it's located in a great neighborhood and is walking distance to benningtons main streetbeautiful apartment with a great locationcomfortable with a good location in the center of towngreat location- close to everything in the city and for wildernessideally situated within walking distance of the heart of bennington downtown highly recommend
8. Guest room in Bennington village home
This private room in Bennington is highly ranked for its super-host, location, and check-in experiences. You’d be living atop a hill that overlooks the Green Mountains of Vermont and Bennington Village. Within, the room comes with a double bed, and 1.5 shared baths. The living room, kitchen, and yard is available for use. Amenities provided include a washer and a dryer, a TV, WiFi, hot water and a hair dryer. Do note that no parties are allowed.
2.73 km (1.7 mi) from Bennington Battle Monument
9. A farmhouse in Bennington
This massive home can fit nine people and is made up of five bedrooms, five beds, and three bathrooms. It is essentially a wonderfully renovated colonial farmhouse that dates back to the 1920s and lies on a 5acre (2.02-hectare) farm. Location wise, you’d be able to drive out to the covered bridges, The Appalachian Trail and the Old Castle Theater. Facilities within include cable TV, a washer and a dryer, WiFi, a kitchen, a patio, and a backyard. The only pets permitted in the unit are dogs, with certain rules in place.
4.39 km (2.8 mi) from Bennington Battle Monument
10. Home with a view of the Green Mountains
This huge home can take in eight guests and is made up of three bedrooms, three bed, and 1.5 baths. You will be able to take a walk down to the restaurants, Bennington Village, museums and breweries too. MassMoca and North Adam can be accessed with a half-hour drive. As far as amenities go, you will be provided with a TV, a washer and a dryer, WiFi, a kitchen and free parking. Do note that there are dogs living on the premise.
2.85 km (1.8 mi) from Bennington Battle Monument
11. Little cottage paradise
This comfortable cottage is ideal for six guests, with three bedrooms, three beds, and a bath. You will be close to all things art and culture, including the Clark Art Museum, Mass MoCA and Robert Frost’s grave. Wake up to the stunning views of the meadow and garden, and enjoy a cup of hot coffee on its porch. Facilities include an indoor fireplace, WiFi, a bathtub, a travel crib, breakfast, kitchen, and barbecue grill. Do note that a no-smoking rule applies.
Bennington, Vermont, United States
1.88 km (1.2 mi) from Bennington Battle Monument
12. Second floor apartment in the town
This sparkling clean apartment comes with two bedrooms, two beds and baths, and is able to fit right up to six guests. What makes it truly strategic is that it’s just 10 minutes away by foot to the village of Bennington, where you’ll have access to galleries, cafes, breweries and the Old Castle. The amenities provided include WiFi, a washer and a dryer, a TV and a kitchenette. Do note that no parties or pets are permitted.
2.01 km (1.3 mi) from Bennington Battle MonumentAccommodates: 6
Top guest reviews
Amenities & Room:
the kitchen was fully stocked and in perfect working orderexcellent welcome and a supremely comfortable apartment close to local amenitiesgreat comfortable space—funky art and lots of spaceCleanliness:
very clean and welcoming environmentthe apartment was exceptionally clean and roomysuch a wonderful space clean and comfortablethe house was roomy very clean and very well decoratedwe were so grateful for a cozy and clean place in the heart of townHost:
friendly and very helpful hostann was a perfect host and she answered ours need in advancethe owner is sweet and left us snacks tips and welcome notesann provided plenty of helpful tips and made sure our stay was enjoyableRead more reviewsLocation:
easy walking distance to main street benningtoneasy drive to places like mass moca and the clark art institute
Have you made up your mind on Bennington yet
It sure looks lovely, doesn’t it? Maybe it’s high time you got to making your travel plans to Bennington, especially as the Airbnb prices are really good right now.
Should you also decide to venture out further into the neighbouring towns, you can check in to some of the best Airbnb vacation rentals in Brattleboro, which is only about an hour’s drive away.
Frequently asked questions about Airbnb vacation rentals in Bennington, Vermont
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
-
Swimming Holes In Vermont, USAHeyleena -
-
-
-
-
-
-
-
-
-
Create an account to