Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cabin in Weare
Lakefront with 2 paddle boards & kayaks
Come relax in this gorgeous, peaceful spot on the lake! 2 decks and fire pit. 2 paddle boards & 2 kayaks. 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
Nov 3 – 10
ﺩ.ﺇ474 per night
4.92 out of 5 average rating, 250 reviews
Guest favorite
Tiny home in Bennington
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.
May 11 – 18
ﺩ.ﺇ551 per night
4.93 out of 5 average rating, 212 reviews
Guest favorite
Home in Antrim
Relaxing Hot Tub Getaway
Come stay at our secluded fully renovated historic home with all new Samsung appliances & furniture. All the necessities for a long or short stay with fully stocked kitchen. A mile from Gregg Lake Beach Professionally cleaned 24/7 Property Manger High speed WiFi ALL YEAR PRIVATE/SECLUDED HOT TUB Fire Pit, Grill, Hammock, Gym equipment Life Size Janga,Yahtzee,Darts,Corn Hole Electric Heating/cooling each room 2 KING PURPLE mattresses 55' Amazon Fire TV 4K in Living Room Vizio 55’ TV in Bedroom
Nov 18 – 25
ﺩ.ﺇ614 per night
4.98 out of 5 average rating, 138 reviews

Popular amenities for Bennington vacation rentals

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

Superhost
Cabin in Stoddard
Waterfront Cabin on Beautiful Highland Lake!
Jun 2 – 9
ﺩ.ﺇ480 per night
4.8 out of 5 average rating, 218 reviews
Guest favorite
Apartment in Hillsboro
Private apartment close to skiing
May 8 – 15
ﺩ.ﺇ317 per night
5.0 out of 5 average rating, 34 reviews
Guest favorite
Cottage in Antrim
Modern Quiet Lakeside Retreat
Sep 3 – 10
ﺩ.ﺇ2,278 per night
4.98 out of 5 average rating, 42 reviews
Guest favorite
Guest suite in Greenfield
Welcome to Merry Hill!
May 31 – Jun 7
ﺩ.ﺇ338 per night
4.93 out of 5 average rating, 59 reviews
Guest favorite
Chalet in Antrim
Direct Waterfront A-Frame, Close to 3 Ski Areas!
Nov 3 – 10
ﺩ.ﺇ809 per night
5.0 out of 5 average rating, 36 reviews
Guest favorite
Guest suite in Weare
Cozy in-law Suite tucked away in the woods
Nov 28 – Dec 5
ﺩ.ﺇ350 per night
4.92 out of 5 average rating, 65 reviews
Guest favorite
Home in Hillsboro
Cottage -Lake and ski!
Apr 18 – 25
ﺩ.ﺇ852 per night
4.91 out of 5 average rating, 11 reviews
Superhost
Cabin in Deering
Secluded Lakeside Cabin
Jun 1 – 8
ﺩ.ﺇ1,047 per night
4.84 out of 5 average rating, 25 reviews
Superhost
Home in Antrim
Quiet House in the Woods
Mar 28 – Apr 4
ﺩ.ﺇ606 per night
4.8 out of 5 average rating, 82 reviews
Guest favorite
Barn in Hancock
4 Bedroom Rustic Home for Special Gatherings
Jul 4 – 9
ﺩ.ﺇ903 per night
4.94 out of 5 average rating, 99 reviews
Guest favorite
Cabin in Deering
The Cabin At Lockehaven Farm
Feb 10 – 17
ﺩ.ﺇ404 per night
4.95 out of 5 average rating, 95 reviews
Guest favorite
Home in Weare
Lakefront -Kayaks,Ski Pats Peak,Fish,Dock
Oct 23 – 30
ﺩ.ﺇ1,473 per night
4.95 out of 5 average rating, 59 reviews

Destinations to explore