Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Guest favorite

Apartment in Bennington

4.94 out of 5 average rating, 154 reviews

NEW Escape the City- Vermont Studio

Our newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Jan 23 – 30

R1,753 ZAR per night

Superhost

Cottage in North Bennington

4.9 out of 5 average rating, 289 reviews

Romantic Private Vermont Cottage - Waterfront

Welcome to beautiful Southern VT! This is a private cottage located in Bennington, VT. The setting is picturesque, on a private lake with diverse wildlife, waterfall and covered bridge. Full kitchen, covered porch, loft bedroom and additional sofa bed. We provide every conceivable amenity for a comfortable stay. A unique retreat for a cozy and peaceful getaway. There is no other vacation property of this quality and character in southern Vermont. Enjoy mornings on your own private lake.

Jul 10 – 15

R4,192 ZAR per night

Superhost

Home in Bennington

4.85 out of 5 average rating, 153 reviews

Bennington Guest Barn 3 Bedrooms

Really sweet 3 complete bedrooms with 1 rollout bed. New & decorated in typical Vermont decor. Many amenities provided to make your stay feel like home. Convenient location: 1 mile to Bennington College, 20 miles to Mass MOCA, Mt. Snow, Jiminy Peak and Bromley are within 30 miles and 8 miles to Cross Country Ski at Prospect Mt. Robert Frost, Bennington Museums along with three unique Covered Bridges are 1 – 3 miles away. Find out why people love Vermont and keep coming back.

Apr 25 – May 2

R2,548 ZAR per night

Guest favorite

Guesthouse in North Bennington

4.98 out of 5 average rating, 150 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned light space with cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. Please note that due to a severe allergy, we cannot accommodate animals.

Oct 8 – 15

R3,133 ZAR per night

Guest favorite

Guest suite in Shaftsbury

4.98 out of 5 average rating, 131 reviews

Country Getaway with a Spa/Birds of a Feather Farm

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. A spa is available and infrared sauna.

Aug 25 – Sep 1

R2,307 ZAR per night

Guest favorite

Cottage in Shaftsbury

4.99 out of 5 average rating, 597 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Nov 12 – 19

R8,251 ZAR per night

Superhost

Cabin in Shaftsbury

4.9 out of 5 average rating, 381 reviews

The LoveNest -Charming private cabin on 65 acres

The Love Nest has returned! We’re high up on the hill yet close to art and culture, great views, restaurants and dining, family-friendly activities, skiing, Bennington, Manchester VT close by. Williamstown Mass not far. A huge yard. You’ll love my place because of the coziness, the light, the comfy bed, the well equipped kitchen, privacy and views, the extreme quiet and relaxation. Waterfalls! My place is good for couples, solo adventurers, and dog guests. 420 friendly!

Aug 20 – 27

R3,183 ZAR per night

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Jun 4 – 11

R1,903 ZAR per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 109 reviews

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

May 2 – 9

R7,117 ZAR per night

Guest favorite

Apartment in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Aug 16 – 23

R1,916 ZAR per night

Guest favorite

Home in Bennington

4.99 out of 5 average rating, 238 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Dec 18 – 25

R5,609 ZAR per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Aug 25 – Sep 1

R1,880 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Bennington vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Bennington's top sights

Bennington Battle Monument72 locals recommend

The Blue Benn40 locals recommend

Madison Brewing Company Pub & Restaurant42 locals recommend

Ramunto's Brick Oven Pizza16 locals recommend

Apple Barn Country Bake Shop10 locals recommend

Sunny Side Diner3 locals recommend

Other great vacation rentals in Bennington

Guest favorite

Cabin in Pownal

4.97 out of 5 average rating, 174 reviews

Historic Cozy Cabin Six

May 16 – 23

R2,039 ZAR per night

Guest favorite

Apartment in Stamford

4.86 out of 5 average rating, 274 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Mar 4 – 11

R2,246 ZAR per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 136 reviews

Beautiful Timber Frame Retreat

Sep 10 – 17

R4,081 ZAR per night

Guest favorite

Home in Pownal

4.99 out of 5 average rating, 211 reviews

Cozy Vermont mini-house

May 20 – 27

R4,072 ZAR per night

Guest favorite

Cabin in Woodford

4.91 out of 5 average rating, 132 reviews

Lakeview Cabin in the Mountains - beautiful

May 23 – 30

R3,422 ZAR per night

Guest favorite

Cabin in Shaftsbury

4.99 out of 5 average rating, 200 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

Jan 10 – 17

R6,427 ZAR per night

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Nov 26 – Dec 3

R1,857 ZAR per night

Guest favorite

Apartment in North Adams

4.97 out of 5 average rating, 405 reviews

See MoCA from your mansion+Sauna! Ski nearby!

Jan 13 – 20

R2,884 ZAR per night

Show all

Quick stats about vacation rentals in Bennington

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
R570 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Bennington?
Yes! Work meets play with ease at over 20 vacation rentals in Bennington featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Bennington?
Four-legged friends are welcome in Bennington. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Bennington?
Bennington has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Bennington have wifi?
Absolutely! We offer over 10 house rentals with wifi in Bennington. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Bennington?
Experience the best of Bennington with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Bennington have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Bennington. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Bennington?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Bennington have free parking?
Absolutely! We offer over 10 house rentals with free parking in Bennington. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Bennington

Top-rated vacation rentals in Bennington

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Bennington vacation rentals

Stay near Bennington's top sights

Other great vacation rentals in Bennington

Cabin in Pownal

Apartment in Stamford

Tiny home in Wilmington

Home in Pownal

Cabin in Woodford

Cabin in Shaftsbury

Guest suite in Williamstown

Apartment in North Adams

Quick stats about vacation rentals in Bennington

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Bennington?

Are there pet-friendly vacation rentals in Bennington?

Are there family-friendly vacation rentals in Bennington?

Do house rentals in Bennington have wifi?

How much does it cost to stay in apartment rentals in Bennington?

Do house rentals in Bennington have air conditioning?

What are the most popular amenities for House Rentals in Bennington?

Do house rentals in Bennington have free parking?

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