House holiday rentals in Chester
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Top-rated house rentals in Chester
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chester
House rentals with a pool
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
22–29 Sep
Home in Plainfield
4.89 out of 5 average rating, 119 reviewsHistoric Home on 17 acres of land. Go escape!
4–11 Apr
Home in Keene
4.93 out of 5 average rating, 182 reviewsThe Brick House on Washington Street
21–28 Apr
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
6–13 Jun
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
18–25 Jun
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
8–15 Aug
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
12–19 Jan
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
18–25 Dec
Weekly house rentals
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
12–19 Jul
Home in Danby
4.97 out of 5 average rating, 198 reviewsComfortable farmhouse with stunning views
10–17 Sep
Home in Mount Holly
4.9 out of 5 average rating, 116 reviewsNewly renovated. Minutes to Slopes & Trails
1–8 Dec
Home in Shaftsbury
4.92 out of 5 average rating, 103 reviewsCheerful 1 bedroom cottage
4–11 Mar
Home in North Adams
4.99 out of 5 average rating, 266 reviewsSteps to MoCA private house + SAUNA!
16–23 Dec
Home in Newfane
4.95 out of 5 average rating, 171 reviewsAdorable home in Newfane
31 Mar – 7 Apr
Home in Jamaica
5.0 out of 5 average rating, 101 reviewsStratton Spa House with Man Cave
28 May – 4 Jun
Home in Granville
4.85 out of 5 average rating, 152 reviewsHome by the Mettowee River- Simply the best!
23–30 Sep
Private house rentals
Home in Chester
4.88 out of 5 average rating, 77 reviewsSpacious Victorian Farmhouse-20 min to Okemo!
9–16 May
Home in Chester
4.92 out of 5 average rating, 26 reviewsPrivate Home in Chester, VT
19–24 May
Home in Chester
4.91 out of 5 average rating, 11 reviewsCharming Chester Farmhouse
18–25 Jun
Home in Chester
4.94 out of 5 average rating, 18 reviewsGetaway at Great Brook
29 Jun – 6 Jul
Home in Chester
4.96 out of 5 average rating, 25 reviewsFarmhouse w/ views close to skiing sauna EV CHRGR
25 Sep – 2 Oct
Home in Chester
4.94 out of 5 average rating, 16 reviewsModern & Cozy Chalet near Okemo Mountain
7–14 May
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
7–14 Jan
Home in Chester
5.0 out of 5 average rating, 14 reviewsMeadow's End Farm: Spring Promotion!
5–12 May
Quick stats about house rentals in Chester
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
$95 SGD before taxes and fees
Destinations to explore
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