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.

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Home in Antrim

Private Hot Tub Suite

Fully renovated in laws suite with private entrance & fully fenced in secluded hot tub. All the necessities for a long or short stay. New Samsung appliances & furniture. Fully stocked kitchen with tons of appliances & Large bathroom A mile from Gregg Lake Beach Professionally cleaned 24/7 Property Manger High speed WiFi XBox Series S ALL YEAR PRIVATE/SECLUDED HOT TUB with gazebo & Hammock 2 KING PURPLE mattresses 55' Amazon Fire TV 4K in Living Room Roku TV in Bedroom Electric Heating/cooling

$152 per night

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Condo in Bennington

Cozy Mountain Retreat, in the Monadnock Region!

Enjoy our cozy, 4 season, condo. Spring and summers invite hiking, kayaking, golfing & good old fashioned relaxing in this light, bright, home located right on the mountainside. The end unit, opens up to panoramic views of the trees and ski slopes from every angle. This is a cozy 1 bedroom (sleeps 4), 1.5 bath condo with gas fireplace, full kitchen & all of the amenities. Scenic Crotched Mtn. Golf Course is next door, offering 18 holes. Enjoy entertainment & dine at historic Toll Booth Tavern!

$110 per night

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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.

$150 per night