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 Putney
4.94 out of 5 average rating, 345 reviewsVermont Botanical Studio Apartment
Guest suite in Brownsville/West Windsor
4.99 out of 5 average rating, 161 reviewsCozy Guest Suite in Charming Farmhouse
Cabin in Jamaica
4.99 out of 5 average rating, 190 reviewsNew Cabin in Jamaica
Barn in Andover
4.98 out of 5 average rating, 110 reviewsFat Cat Barn - Close Okemo & Magic, Vermont
Apartment in Weathersfield
4.97 out of 5 average rating, 113 reviewsCute VT Bungalow With 180 Degree View of NH
Guesthouse in Putney
4.94 out of 5 average rating, 325 reviewsA Vermont Carriage House
Home in Chester
5.0 out of 5 average rating, 17 reviewsCozy 1850 farmhouse in Stone Village of Chester
Guest suite in Chester
4.84 out of 5 average rating, 44 reviewsAdorable, Cozy 2 bedroom apartment walk to village
Other great vacation rentals in Chester
Home in Chester
4.93 out of 5 average rating, 14 reviewsCharming Chester Farmhouse
Home in Chester
4.94 out of 5 average rating, 31 reviewsStunning farmhouse in historical village
Place to stay in Town of Rockingham
4.92 out of 5 average rating, 62 reviewsRomantically Cheerful Country Cottage apt.
Farm stay in Baltimore
4.92 out of 5 average rating, 98 reviewsHawk Mtn Farm's lovely one bedroom apartment!
Cottage in Ludlow
5.0 out of 5 average rating, 13 reviewsThe Little House
Home in Chester
5.0 out of 5 average rating, 16 reviewsMountain Views, hiking, biking, 4 bedroom 6 acres
Vacation home in Town of Rockingham
4.96 out of 5 average rating, 54 reviewsCozy studio at Leslie's Tavern in Rockingham
Home in Chester
5.0 out of 5 average rating, 14 reviewsSpectacular VT Farmhouse on 11 Private Acres!
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
$60 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 10 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 10 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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