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

4.92 out of 5 average rating, 249 reviews

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

Sep 21 – 28

R2,816 ZAR per night
Guest favorite

Yurt in Bennington

4.95 out of 5 average rating, 180 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.

May 5 – 12

R2,954 ZAR per night
Guest favorite

Apartment in Dublin

4.96 out of 5 average rating, 177 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.

Aug 31 – Sep 7

R2,099 ZAR per night

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

Guest favorite

Guest suite in Fitzwilliam

4.96 out of 5 average rating, 283 reviews

The Carriage House in Historic Fitzwilliam

Dec 22 – 29

R1,756 ZAR per night
Guest favorite

Guest suite in Merrimack

4.99 out of 5 average rating, 144 reviews

Guest suite with king bed and private entrance

May 17 – 24

R1,738 ZAR per night
Guest favorite

Guest suite in Milford

5.0 out of 5 average rating, 126 reviews

Spacious Souhegan Getaway

Jun 25 – Jul 2

R2,040 ZAR per night
Guest favorite

Guest suite in Greenfield

4.93 out of 5 average rating, 59 reviews

Welcome to Merry Hill!

May 18 – 25

R1,796 ZAR per night
Guest favorite

Apartment in Hillsboro

5.0 out of 5 average rating, 34 reviews

Private apartment close to skiing

Apr 19 – 26

R1,878 ZAR per night
Guest favorite

Guest suite in Weare

4.92 out of 5 average rating, 66 reviews

Cozy in-law Suite tucked away in the woods

Sep 30 – Oct 7

R2,084 ZAR per night
Guest favorite

Cabin in Deering

4.95 out of 5 average rating, 95 reviews

The Cabin At Lockehaven Farm

Feb 28 – Mar 7

R2,383 ZAR per night
Guest favorite

Chalet in Antrim

5.0 out of 5 average rating, 35 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

Nov 1 – 8

R4,773 ZAR per night
Guest favorite

Farm stay in Stoddard

5.0 out of 5 average rating, 77 reviews

Upton Farm and Forest

Aug 14 – 21

R3,241 ZAR per night
Guest favorite

Apartment in Peterborough

5.0 out of 5 average rating, 19 reviews

Studio Apt with Full Kitchen

May 2 – 9

R2,189 ZAR per night
Guest favorite

Cottage in Antrim

4.98 out of 5 average rating, 42 reviews

Modern Quiet Lakeside Retreat

Aug 26 – Sep 2

R14,859 ZAR per night
Guest favorite

Home in Antrim

5.0 out of 5 average rating, 82 reviews

Private Hot Tub Suite

Mar 1 – 8

R3,354 ZAR per night

Destinations to explore