Chester vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chester
Guests agree: these vacation rentals 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 vacation rentals
Other great vacation rentals in Chester
Apartment in Claremont
4.88 out of 5 average rating, 110 reviewsBeautiful 1 bedroom apartment with balcony
Jul 15 – 22
Condo in Ludlow
4.99 out of 5 average rating, 100 reviewsUpdated Main St Condo in downtown Ludlow!
Jun 2 – 9
Cabin in Rochester
4.95 out of 5 average rating, 391 reviewsBlack haus: a hip, cool house hidden in a forest.
Jan 16 – 23
Tiny home in Athens
4.95 out of 5 average rating, 148 reviewsLuxury “Tiny” House, Immersed In Nature (Timbery)
Feb 15 – 22
Guesthouse in Wallingford
4.98 out of 5 average rating, 588 reviewsVermont Home Central to Ski Areas-No Cleaning Fees
Nov 20 – 27
Cabin in Jamaica
4.99 out of 5 average rating, 185 reviewsNew Cabin in Jamaica
Jun 24 – Jul 1
Cabin in West Windsor
4.98 out of 5 average rating, 205 reviewsSunset Cabin - your private romantic hideaway
Jul 2 – 9
Barn in Andover
4.98 out of 5 average rating, 109 reviewsFat Cat Barn - Close Okemo & Magic, Vermont
May 9 – 16
Other great vacation rentals in Chester
Guest suite in Chester
4.84 out of 5 average rating, 44 reviewsAdorable, Cozy 2 bedroom apartment walk to village
Mar 6 – 13
Guest suite in Chester
4.93 out of 5 average rating, 14 reviewsStone Village Private Studio
Sep 28 – Oct 5
Farm stay in Chester
4.98 out of 5 average rating, 40 reviewsRivers Edge Farm’s Cozy Cabin
Jul 5 – 10
Tiny home in Chester
5.0 out of 5 average rating, 80 reviewsBearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Jan 19 – 26
Home in Chester
5.0 out of 5 average rating, 16 reviewsCozy 1850 farmhouse in Stone Village of Chester
Dec 25 – Jan 1
Home in Chester
4.92 out of 5 average rating, 26 reviewsPrivate Home in Chester, VT
May 15 – 22
Guesthouse in Grafton
4.89 out of 5 average rating, 91 reviewsVT Sugar House-Guesthouse
May 8 – 15
Loft in Town of Rockingham
5.0 out of 5 average rating, 32 reviewsSaxtons River Studio apartment
Feb 14 – 21
Quick stats about vacation rentals in Chester
Total rentals
90 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.1K reviews
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Frequently Asked Questions
Are there pet-friendly vacation rentals in Chester?
Four-legged friends are welcome in Chester. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 40 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chester have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chester?
Chester has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chester have wireless internet?
Absolutely! We offer over 50 house rentals with wireless internet in Chester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with a bbq area, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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