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Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Tiny home in Bennington

4.93 out of 5 average rating, 215 reviews

Waterfront Tiny House-Swim, Canoe, Hike, Golf,MORE

Waterfront oasis. Relax in fully equipped Tiny House with wifi, cable tv, bath & shower tucked in a private wooded setting overlooking a 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 hours from Boston or 2.25 hrs. from Hartford in legendary Monadnock Region.

Aug 25 – Sep 1

G$36,220 GYD per night

Cabin in Weare

4.92 out of 5 average rating, 254 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

Apr 11 – 18

G$35,856 GYD per night

Apartment in Dublin

4.96 out of 5 average rating, 184 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 15 – 22

G$22,794 GYD per night

Cabin in Bradford

4.98 out of 5 average rating, 334 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

Jan 10 – 17

G$30,154 GYD per night

Guest suite in Deering

5.0 out of 5 average rating, 225 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.

Dec 13 – 20

G$18,973 GYD per night

Cabin in Marlow

4.97 out of 5 average rating, 111 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.

Mar 27 – Apr 3

G$26,205 GYD per night

Cottage in Weare

4.94 out of 5 average rating, 259 reviews

Seasonal lake side cottage

Cottage comes with the use of two kayak's, a canoe, two stand up paddle boards, an outside fire place to roast s'mores. (Please do not use fireplace until dusk). Refrigerator & freezer, microwave, keurig, toaster, basic pots and pans, outside grill,a clean lake with swimming area. Tv/DVD player & DVD’s(no cable). We supply towels,linens & beach towels. Friendly neighbors on either side of cottage. Water is fine to use, but not to drink. No wifi. A perfect relaxing, unplugged weekend getaway.

Mar 9 – 16

G$34,820 GYD per night

Guesthouse in Wilton

4.95 out of 5 average rating, 573 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.

Sep 20 – 27

G$31,535 GYD per night

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 3 – 10

G$27,025 GYD per night

Guest suite in Merrimack

4.99 out of 5 average rating, 150 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

Jun 9 – 16

G$19,142 GYD per night

Chalet in Stoddard

4.95 out of 5 average rating, 195 reviews

Highland Haus- Cozy 70s AFrame- short walk to lake

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. In warmer months, guests will have access to our canoe. 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 all-wheel drive or 4-wheel drive is recommended.

Jul 24 – 31

G$34,470 GYD per night

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.

Dec 7 – 14

G$36,638 GYD per night

Vacation rentals for every style

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Stylish accommodations and amenities

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Homes

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Popular amenities for Bennington vacation rentals

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

Home in Mont Vernon

4.96 out of 5 average rating, 136 reviews

Serenity on the Pond ~ Private Waterfront, Hot Tub

Aug 23 – 30

G$193,851 GYD per night

Guesthouse in New Ipswich

4.94 out of 5 average rating, 299 reviews

"The Porch" Your cozy home away from home!

Nov 21 – 28

G$17,657 GYD per night

Barn in Chester

4.99 out of 5 average rating, 496 reviews

Inviting studio apartment above barn in Vermont

Sep 28 – Oct 5

G$21,625 GYD per night

Home in Peterborough

4.97 out of 5 average rating, 102 reviews

Cozy New England Cape (2mi from town)

Jul 21 – 28

G$50,801 GYD per night

Guest suite in Greenfield

4.94 out of 5 average rating, 63 reviews

Welcome to Merry Hill!

Aug 31 – Sep 7

G$22,419 GYD per night

Guest suite in Weare

4.93 out of 5 average rating, 68 reviews

Cozy in-law Suite tucked away in the woods

Dec 8 – 15

G$23,204 GYD per night

Farm stay in Stoddard

5.0 out of 5 average rating, 78 reviews

Upton Farm and Forest

Sep 26 – Oct 3

G$35,695 GYD per night

Cabin in Deering

4.95 out of 5 average rating, 98 reviews

The Cabin At Lockehaven Farm

Apr 15 – 22

G$26,239 GYD per night

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$8,341 GYD before taxes and fees

Destinations to explore