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
Home in Ludlow
4.92 out of 5 average rating, 139 reviews149 Upper Crossroad Unit A
Jun 18 – 25
Tiny home in Athens
4.95 out of 5 average rating, 147 reviewsLuxury “Tiny” House, Immersed In Nature (Timbery)
Jul 12 – 19
Home in Putney
4.94 out of 5 average rating, 336 reviewsVermont Botanical Studio Apartment
Dec 5 – 12
Apartment in Town of Rockingham
4.82 out of 5 average rating, 159 reviewsApartment on Main Street
Sep 29 – Oct 6
Guest suite in West Windsor
4.9 out of 5 average rating, 102 reviewsNewly renovated private space on Ascutney Trails
Dec 9 – 16
Home in S Londonderry
4.95 out of 5 average rating, 270 reviewsCozy barn apartment in So. Vermont
Mar 5 – 12
Apartment in Weston
4.86 out of 5 average rating, 128 reviewsCozy Guesthouse in Heart of VT
Jul 30 – Aug 6
Home in Chester
5.0 out of 5 average rating, 16 reviewsCozy 1850 farmhouse in Stone Village of Chester
Jan 27 – Feb 3
Other great vacation rentals in Chester
Home in Chester
4.91 out of 5 average rating, 11 reviewsCharming Chester Farmhouse
Jul 2 – 9
Vacation home in Cavendish
4.84 out of 5 average rating, 32 reviewsCozy 1 bd Apt Minutes to Okemo & Pet Friendly
Jun 1 – 8
Home in Chester
4.92 out of 5 average rating, 26 reviewsPrivate Home in Chester, VT
Jan 4 – 11
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
Sep 27 – Oct 4
Cottage in Ludlow
5.0 out of 5 average rating, 13 reviewsThe Little House
Jul 10 – 17
Farm stay in Baltimore
4.92 out of 5 average rating, 96 reviewsHawk Mtn Farm's lovely one bedroom apartment!
Jun 25 – Jul 2
Cottage in Chester
4.92 out of 5 average rating, 60 reviewsQuaint stone house!
Nov 27 – Dec 4
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
R1,150 ZAR 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 20 homes with a bbq area, over 30 homes with air conditioning, over 50 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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