Chester vacation rentals
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Top-rated vacation rentals in Chester
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Apartment in Springfield
4.9 out of 5 average rating, 221 reviewsFarm Barn apt. 3 bedr, 2 bath, fiberoptic internet
Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.
Apr 16 – 23
Cabin in Londonderry
4.93 out of 5 average rating, 308 reviewsStone Fence Cabin
Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!
Oct 4 – 11
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.
Dec 31 – Jan 7
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 4 – 11
Tiny home in Jamaica
4.84 out of 5 average rating, 210 reviewsHot Tub Farmhouse - Buttercup Studio - Jamaica VT.
Oct 19 – 26
Cottage in Reading
4.95 out of 5 average rating, 128 reviewsShattuck Hill Cottage
Mar 15 – 22
Home in Putney
4.94 out of 5 average rating, 332 reviewsVermont Botanical Studio Apartment
Nov 25 – Dec 2
Apartment in Weston
4.86 out of 5 average rating, 128 reviewsCozy Guesthouse in Heart of VT
Jul 8 – 15
Apartment in Weathersfield
4.97 out of 5 average rating, 109 reviewsCute VT Bungalow With 180 Degree View of NH
Jun 19 – 26
Apartment in Town of Rockingham
4.82 out of 5 average rating, 158 reviewsApartment on Main Street
Apr 27 – May 4
Tiny home in Athens
4.95 out of 5 average rating, 144 reviewsLuxury “Tiny” House, Immersed In Nature (Timbery)
May 4 – 11
Guest suite in West Windsor
4.91 out of 5 average rating, 100 reviewsNewly renovated private space on Ascutney Trails
Sep 14 – 21
Cabin in Grafton
4.98 out of 5 average rating, 170 reviewsPeaceful log cabin retreat...
Dec 12 – 19
Cabin in West Windsor
4.98 out of 5 average rating, 205 reviewsSunset Cabin - your private romantic hideaway
Sep 5 – 12
Guest suite in Brattleboro
4.94 out of 5 average rating, 515 reviewsCharming studio in renovated 19th century church.
Oct 17 – 24
Other great vacation rentals in Chester
Farm stay in Chester
4.97 out of 5 average rating, 37 reviewsRivers Edge Farm’s Cozy Cabin
Sep 16 – 21
Place to stay in Town of Rockingham
4.92 out of 5 average rating, 61 reviewsRomantically cheerful one-bedroom suite
May 10 – 17
Home in Chester
4.92 out of 5 average rating, 26 reviewsStunning farmhouse in historical village
Aug 20 – 27
Guesthouse in Grafton
4.89 out of 5 average rating, 90 reviewsVT Sugar House-Guesthouse
Oct 22 – 29
Tiny home in Chester
5.0 out of 5 average rating, 18 reviewsZen of the Woods Tiny Cabin in Okemo Valley
May 3 – 10
Farm stay in Baltimore
4.93 out of 5 average rating, 94 reviewsHawk Mtn Farm's lovely one bedroom apartment!
Apr 10 – 17
Loft in Town of Rockingham
5.0 out of 5 average rating, 31 reviewsSaxtons River Studio apartment
Nov 28 – Dec 5
Home in Chester
5.0 out of 5 average rating, 16 reviewsMountain Views, hiking, biking, 4 bedroom 6 acres
Apr 15 – 22
Condo in Cavendish
5.0 out of 5 average rating, 20 reviewsOne Bedroom Suite Near Okemo
Apr 20 – 27
Cabin in Cavendish
4.88 out of 5 average rating, 17 reviewsCaretaker’s Cottage
Jun 13 – 20
Cottage in Chester
4.93 out of 5 average rating, 59 reviewsQuaint stone house!
Sep 19 – 26
Vacation home in Town of Rockingham
4.96 out of 5 average rating, 51 reviewsCozy studio at Leslie's Tavern in Rockingham
Jul 14 – 21
Quick stats about vacation rentals in Chester
Total rentals | 80 properties |
---|---|
Rentals with dedicated workspaces | 30 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 | 2.7K reviews |
Nightly prices starting at | € 74 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 30 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 $90 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 40 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 50 homes with wireless internet, over 20 homes with a bbq area, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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