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House vacation rentals in Bennington

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Top-rated house rentals in Bennington

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Home in Putney

4.88 out of 5 average rating, 170 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Home in Petersburg

5 out of 5 average rating, 103 reviews

Private Mountain Lodge-Amazing views, cozy vibes

Book your holiday get away! An incredible "wrapped in nature" experience in your own private lodge! Just 3 hours from NYC and Boston, perfect for those looking for privacy, views and luxury conveniences and events. Outdoor hot tub, sauna, game room/bar area, kitchen, large yard, fire pit, Peloton bike, local lake access and skiing! Something for everyone! All season fun-hiking, concerts, shopping, skiing, fishing, and world class art. Near Williamstown, MA, Southern VT, and so much more.

Home in Bennington

4.88 out of 5 average rating, 126 reviews

Bennington Guest Farmhouse 5 Bedrooms

Large Gracious Victorian Farmhouse 1 mile from Benningtgon College lovingly restored to accommodate nine guests in a quaint relaxed convenient atmosphere. Fully restored farmhouse with all new mattresses, bedding and ample amenities to make your stay an enjoyable and memorable experience. Within a short drive you will find other colleges, museums ski areas and attractions. Tour our beautiful maple syrup countryside and sites that keep people coming back to our beautiful state of Vermont.

Home in Putney

4.94 out of 5 average rating, 369 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Home in Winhall

4.95 out of 5 average rating, 194 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Home in Shaftsbury

4.85 out of 5 average rating, 118 reviews

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Home in Bennington

4.99 out of 5 average rating, 124 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.

Home in Bennington

4.99 out of 5 average rating, 268 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.

Home in North Adams

4.98 out of 5 average rating, 341 reviews

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis right above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate that belonged to the owners of APW factory (now the museum). Steps to downtown & restaurants. 10 min drive to Williams & Clark. Now part of @chasehillartistretreat. Your stay enables us to host refugee & immigrant musicians pro bono year-round.

Home in New Lebanon

4.99 out of 5 average rating, 360 reviews

The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.

Home in Albany

4.82 out of 5 average rating, 716 reviews

Alb hospital area studio bath wifi. (Red)

Spacious warm studio in 1840 house close to hospitals and downtown. Own bath flat screen cable tv wireless internet ground floor. Double bed coffee tea fridge microwave and parking. Suit 1. On park walk to post office cvs Chinese sports bar. Comfortable and decorated with taste. Irish host

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Popular amenities for Bennington house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

Home in Colrain

4.89 out of 5 average rating, 121 reviews

The 1770 House

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Ghent

4.88 out of 5 average rating, 301 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Home in Corinth

4.99 out of 5 average rating, 197 reviews

Beautiful HotTub and Pool Home Adirondacks

Home in Granville

4.95 out of 5 average rating, 102 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

Home in Queensbury

4.8 out of 5 average rating, 311 reviews

Rustic Lake George Mega-Lodge+Indr🔥Tub+Sauna+Pool

Home in Wilmington

4.83 out of 5 average rating, 162 reviews

The Vermont Barn (Mount Snow)

Weekly house rentals

Home in Schenectady

4.98 out of 5 average rating, 189 reviews

Bright & Clean ~Tons of Upgrades ~Office Space

Home in Williamstown

4.98 out of 5 average rating, 125 reviews

Quality, Comfort, Charm in Williamstown Center

Home in Brattleboro

4.95 out of 5 average rating, 166 reviews

Frosted Willows

Home in Bennington

5 out of 5 average rating, 35 reviews

The Vermont Farmhouse+Holidays+Skiing+Dog Friendly

Home in Londonderry

4.98 out of 5 average rating, 114 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

Home in Ballston Spa

4.93 out of 5 average rating, 123 reviews

Legend Ln Saratoga Track Rental

Home in Bennington

5 out of 5 average rating, 10 reviews

Green Mountain Getaway

Home in Newfane

4.94 out of 5 average rating, 181 reviews

Adorable home in Newfane

Private house rentals

Home in Bennington

4.97 out of 5 average rating, 76 reviews

Bright and Cozy Home in Town!

Home in Shaftsbury

4.99 out of 5 average rating, 67 reviews

VT Mountain House Epic Views 350 Acre Farm Hot Tub

Home in Pownal

4.91 out of 5 average rating, 23 reviews

Modern Farmhouse Retreat

Home in Woodford

4.92 out of 5 average rating, 25 reviews

Green Mountains Lake Retreat - Hidden Gem

Home in Woodford

5 out of 5 average rating, 14 reviews

Bright airy cottage w/ lake view

Home in Bennington

4.79 out of 5 average rating, 19 reviews

Farmhouse w Creek View Village of North Bennington

Home in Bennington

4.99 out of 5 average rating, 68 reviews

Stylish dreamy VT cabin with fast & reliable wifi

Home in Bennington

4.89 out of 5 average rating, 27 reviews

Cozy Ski Stay w/Bar Room, Hot Tub Near Mt. Snow

Quick stats about house rentals in Bennington

Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
890 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore