House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester house rentals
House rentals with a pool
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
Nov 18 – 25
Home in Plainfield
4.89 out of 5 average rating, 118 reviewsHistoric Home on 17 acres of land. Go escape!
Nov 22 – 29
Home in Keene
4.93 out of 5 average rating, 182 reviewsThe Brick House on Washington Street
Mar 13 – 20
Home in Mendon
4.88 out of 5 average rating, 210 reviewsRanch at Mendon Mt Orchards
Sep 11 – 18
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
Jun 3 – 10
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
Aug 11 – 18
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Oct 2 – 9
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Feb 21 – 28
Weekly house rentals
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
Jun 17 – 24
Home in Mount Holly
4.9 out of 5 average rating, 116 reviewsNewly renovated. Minutes to Slopes & Trails
Dec 1 – 8
Home in Danby
4.97 out of 5 average rating, 198 reviewsComfortable farmhouse with stunning views
Sep 10 – 17
Home in Shaftsbury
4.92 out of 5 average rating, 103 reviewsCheerful 1 bedroom cottage
Mar 4 – 11
Home in Newfane
4.95 out of 5 average rating, 170 reviewsAdorable home in Newfane
Mar 31 – Apr 7
Home in Pownal
4.99 out of 5 average rating, 213 reviewsCozy Vermont mini-house
Dec 14 – 21
Home in Granville
4.85 out of 5 average rating, 152 reviewsHome by the Mettowee River- Simply the best!
Sep 25 – Oct 2
Home in Jamaica
5.0 out of 5 average rating, 100 reviewsStratton Spa House with Man Cave
May 28 – Jun 4
Private house rentals
Home in Chester
4.91 out of 5 average rating, 11 reviewsCharming Chester Farmhouse
Jun 18 – 25
Home in Chester
4.96 out of 5 average rating, 24 reviewsFarmhouse w/ views close to skiing sauna EV CHRGR
Sep 25 – Oct 2
Home in Chester
4.88 out of 5 average rating, 77 reviewsSpacious Victorian Farmhouse-20 min to Okemo!
Apr 3 – 10
Home in West Windsor
4.96 out of 5 average rating, 56 reviewsBirdie's Nest Guesthouse
Feb 19 – 26
Home in Chester
5.0 out of 5 average rating, 14 reviewsMeadow's End Farm: Spring Promotion!
Nov 3 – 10
Home in Grafton
4.92 out of 5 average rating, 59 reviewsGrafton Artist Retreat With Pond Near Skiing
Nov 16 – 23
Home in Chester
4.93 out of 5 average rating, 28 reviewsStunning farmhouse in historical village
Sep 29 – Oct 6
Home in Chester
4.94 out of 5 average rating, 16 reviewsModern & Cozy Chalet near Okemo Mountain
Aug 30 – Sep 6
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
€ 65 before taxes and fees
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