House vacation rentals in Cheshire County
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Top-rated house rentals in Cheshire County
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cheshire County house rentals
House rentals with a pool
Home in Winchendon
The Perfect Spot at the Lake @ Tatum's Place
Home in Troy
5 out of 5 average rating, 3 reviewsMountain View escape
Home in Surry
4.71 out of 5 average rating, 34 reviewsBright, Large, Spacious Family Home
Home in Rindge
New place to stayThe Shoreline
Home in Keene
Dog friendly, Immaculate!
Home in Winchendon
Amazing Lakefront Home with Pool- Tatum's Place
Weekly house rentals
Home in Keene
4.96 out of 5 average rating, 55 reviewsKeene Center Farmhouse: Large & Cozy + Hot Tub
Home in Chesterfield
4.92 out of 5 average rating, 88 reviewsGoverner's Brook Camp - 2 Bedroom
Home in Swanzey
4.92 out of 5 average rating, 25 reviewsHillside Haven: Luxe Farm Escape | 5BR-2 King Beds
Home in Keene
4.98 out of 5 average rating, 44 reviewsWinfield & Boots Downtown Retreat
Home in Rindge
5 out of 5 average rating, 81 reviewsWaterfront escape
Home in Rindge
5 out of 5 average rating, 65 reviewsThe Crowcroft House
Home in Keene
4.9 out of 5 average rating, 68 reviewsSweet Home
Home in Rindge
5 out of 5 average rating, 29 reviewsLake house on walking trail near mountain
Private house rentals
Home in Spofford
5 out of 5 average rating, 8 reviewsA-Frame Cottage at Lake Spofford
Home in Washington
5 out of 5 average rating, 82 reviewsNewer Home on quiet 200 acre lake - sleeps 6
Home in Hillsboro
5 out of 5 average rating, 22 reviewsYour private lake retreat awaits
Home in Brattleboro
5 out of 5 average rating, 8 reviewsSunny Garden House
Home in Putney
4.9 out of 5 average rating, 10 reviewsBeautiful 5-Bedroom Country Home with Home Theater
Home in Hillsboro
4.87 out of 5 average rating, 15 reviewsCottage -Lake and ski!
Home in Spofford
4.71 out of 5 average rating, 34 reviewsPenthouse, steps to the sandy beach & clear water
Home in Hancock
4.94 out of 5 average rating, 80 reviewsLarge Home in Peaceful Historical Village
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