Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Guest favorite

Yurt in Bennington

4.95 out of 5 average rating, 184 reviews

Experience a Romantic Yurt!-Relax by the Water!

Waterfront oasis. Relax in cozy yurt fully equipped with wifi, cable tv, private bath & outdoor shower tucked in wooded setting overlooking small waterfall in nature's paradise on Powder Mill Pond and Contoocook River. Hike, Swim, Fish, Kayak, Canoe, Paddle boat. Private fire pit. Hot tub. Eclectic dining, 4 golf courses, shops, breweries, skiing all nearby. Just outside of Peterborough in Southern New Hampshire, only 1.5 hrs from Boston or 2.25 hrs. from Hartford in legendary Monadnock Region.

Dec 3 – 10

G$32,518 GYD per night

Guest favorite

Cabin in Weare

4.92 out of 5 average rating, 253 reviews

Lakefront with 2 paddle boards

Come relax in our gorgeous, peaceful spot on the lake! No children. decks and fire pit. 2 paddle boards. One bedroom w double bed plus one loft w double bed. Cozy living room stocked w boards games, Roku & DVDs. Great WiFi, full kitchen and full bath. 10 minutes from Pats Peak, 30 minutes from Concord. 15 minutes from either direction, are small charming towns w locally owned businesses. No smoking. 3 guest limit! Special packages available. See photos. Fines will be levied for rules broken

Sep 2 – 9

G$32,110 GYD per night

Guest favorite

Apartment in Dublin

4.96 out of 5 average rating, 182 reviews

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Oct 12 – 19

G$22,731 GYD per night

Guest favorite

Cabin in Bradford

4.98 out of 5 average rating, 332 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

Dec 25 – Jan 1

G$30,495 GYD per night

Guest favorite

Guest suite in Deering

5.0 out of 5 average rating, 223 reviews

Elegant Lodging in the Woods ~Privacy & Comfort!

Come relax and unwind in this nicely appointed secluded, guest suite. Privacy guaranteed in this smoke free “home away from home”. Country setting surrounded by mountains, lakes, hiking, golfing, Pat's Peak, Crotched Mtn. and Mt. Sunapee. Convenient location for day trips to the seacoast, Concord or Peterborough. Cozy cathedral ceiling bedroom/living room studio, private bathroom, kitchenette/workroom. Super clean! Private locked entrance. FREE onsite parking. Only 75 minutes from Boston.

Sep 1 – 8

G$19,208 GYD per night

Guest favorite

Cabin in Marlow

4.97 out of 5 average rating, 109 reviews

The Birches Cabin, at home in the woods!

The Birches is situated on 10 secluded acres, where guests will enjoy the privacy and scenery the cabin offers. Built in 2020 and designed to accommodate guests. During your stay take a walk on the property, read a book, enjoy a glass a wine, cook a fine meal, and stare at the stars. Centrally between Keene and the Sunapee region, guests have many options on how to enjoy their days such as Skiing, Hiking, Paddling, and Snow tubing. This is a vacation spot, that can be enjoyed all year.

Dec 4 – 11

G$24,830 GYD per night

Guest favorite

Guesthouse in Wilton

4.95 out of 5 average rating, 572 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Oct 28 – Nov 4

G$31,529 GYD per night

Superhost

Cabin in Stoddard

4.82 out of 5 average rating, 111 reviews

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Sep 16 – 23

G$27,020 GYD per night

Guest favorite

Guesthouse in New Ipswich

4.94 out of 5 average rating, 296 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out at, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person rentals. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome!

Nov 5 – 12

G$17,654 GYD per night

Guest favorite

Chalet in Stoddard

4.95 out of 5 average rating, 195 reviews

Highland Haus- Cozy 70s AFrame- two wood stoves

Cozy 1975 A-frame chalet cabin sleeps 4 with a comfortable living space, two wood stoves, and a full kitchen. Located in the rural community of Stoddard. Enjoy the peace and quiet that this area has to offer. Many local hiking, swimming and fishing nearby. It is less than a 2-hour drive from Boston to the Highland Haus! Winter Guests- please note that Shedd Hill rd is very hilly and can be difficult to drive after a fresh snowstorm, all-wheel drive or 4-wheel drive is recommended.

Jul 11 – 18

G$33,857 GYD per night

Guest favorite

Loft in Peterborough

4.96 out of 5 average rating, 268 reviews

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

May 5 – 12

G$28,328 GYD per night

Guest favorite

Home in Greenfield

4.93 out of 5 average rating, 119 reviews

Charming House on 7 Acres in Rural New Hampshire

This magical place has been our home away from home for twenty years and we are excited to share it with you. We hope you'll experience the same time-out-of-time feeling we get when sitting out on the deck in the early morning or looking up on a moonless night as the Milky Way snakes its way across the dark sky. The house sits on seven mostly wooded acres that abut a scenic beaver pond. The property is located on a quiet unpaved road in rural New Hampshire.

Jan 2 – 9

G$36,630 GYD 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

Rick & Diane's5 locals recommend

Alberto's Italian Restaurant3 locals recommend

Tenney Farm4 locals recommend

Other great vacation rentals in Bennington

Guest favorite

Home in Mont Vernon

4.96 out of 5 average rating, 134 reviews

Serenity on the Pond ~ Private Waterfront, Hot Tub

Sep 13 – 20

G$167,218 GYD per night

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 196 reviews

Cozy cottage loft and retreat

Jul 22 – 29

G$18,764 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

Sep 4 – 11

G$21,418 GYD per night

Guest favorite

Cottage in Weare

4.94 out of 5 average rating, 259 reviews

Seasonal lake side cottage

Feb 5 – 12

G$34,813 GYD per night

Guest favorite

Cabin in Washington

4.9 out of 5 average rating, 191 reviews

Cozy Camp in the woods surrounded by nature.

Mar 1 – 8

G$30,208 GYD per night

Guest favorite

Guest suite in Greenfield

4.94 out of 5 average rating, 62 reviews

Welcome to Merry Hill!

Jul 9 – 16

G$21,955 GYD per night

Guest favorite

Home in Antrim

5.0 out of 5 average rating, 88 reviews

Private Hot Tub Suite

Jan 28 – Feb 4

G$35,646 GYD per night

Guest favorite

Guest suite in Weare

4.93 out of 5 average rating, 67 reviews

Cozy in-law Suite tucked away in the woods

Dec 25 – Jan 1

G$23,878 GYD per night

Show all

Quick stats about vacation rentals in Bennington

Total rentals
10 properties
Local attractions
Rick & Diane's, Alberto's Italian Restaurant, and Common Place Eatery
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
580 reviews
Nightly prices starting at
G$8,339 GYD before taxes and fees

Vacation rentals in Bennington

Top-rated vacation rentals in Bennington

Yurt in Bennington

Cabin in Weare

Apartment in Dublin

Cabin in Bradford

Guest suite in Deering

Cabin in Marlow

Guesthouse in Wilton

Cabin in Stoddard

Guesthouse in New Ipswich

Chalet in Stoddard

Loft in Peterborough

Home in Greenfield

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

Home in Mont Vernon

Guesthouse in Putney

Barn in Chester

Cottage in Weare

Cabin in Washington

Guest suite in Greenfield

Home in Antrim

Guest suite in Weare

Quick stats about vacation rentals in Bennington

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore