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.

Guest favorite

Apartment in Springfield

4.9 out of 5 average rating, 221 reviews

Farm 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

€ 107 per night
Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone 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

€ 112 per night
Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut 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

€ 96 per night

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Country Girl Diner29 locals recommend
MacLaomainn's Scottish Pub31 locals recommend
The Pizza Stone VT.27 locals recommend
Fullerton Inn12 locals recommend
Southern Pie Cafe18 locals recommend
the Free Range15 locals recommend

Other great vacation rentals in Chester

Guest favorite

Home in Ludlow

4.92 out of 5 average rating, 139 reviews

149 Upper Crossroad Unit A

Jun 4 – 11

€ 117 per night
Guest favorite

Tiny home in Jamaica

4.84 out of 5 average rating, 210 reviews

Hot Tub Farmhouse - Buttercup Studio - Jamaica VT.

Oct 19 – 26

€ 113 per night
Guest favorite

Cottage in Reading

4.95 out of 5 average rating, 128 reviews

Shattuck Hill Cottage

Mar 15 – 22

€ 124 per night
Guest favorite

Home in Putney

4.94 out of 5 average rating, 332 reviews

Vermont Botanical Studio Apartment

Nov 25 – Dec 2

€ 119 per night
Superhost

Apartment in Weston

4.86 out of 5 average rating, 128 reviews

Cozy Guesthouse in Heart of VT

Jul 8 – 15

€ 117 per night
Guest favorite

Apartment in Weathersfield

4.97 out of 5 average rating, 109 reviews

Cute VT Bungalow With 180 Degree View of NH

Jun 19 – 26

€ 180 per night
Superhost

Apartment in Town of Rockingham

4.82 out of 5 average rating, 158 reviews

Apartment on Main Street

Apr 27 – May 4

€ 66 per night
Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 144 reviews

Luxury “Tiny” House, Immersed In Nature (Timbery)

May 4 – 11

€ 266 per night
Guest favorite

Guest suite in West Windsor

4.91 out of 5 average rating, 100 reviews

Newly renovated private space on Ascutney Trails

Sep 14 – 21

€ 122 per night
Guest favorite

Cabin in Grafton

4.98 out of 5 average rating, 170 reviews

Peaceful log cabin retreat...

Dec 12 – 19

€ 231 per night
Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 205 reviews

Sunset Cabin - your private romantic hideaway

Sep 5 – 12

€ 165 per night
Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 515 reviews

Charming studio in renovated 19th century church.

Oct 17 – 24

€ 101 per night

Other great vacation rentals in Chester

Guest favorite

Farm stay in Chester

4.97 out of 5 average rating, 37 reviews

Rivers Edge Farm’s Cozy Cabin

Sep 16 – 21

€ 97 per night
Guest favorite

Place to stay in Town of Rockingham

4.92 out of 5 average rating, 61 reviews

Romantically cheerful one-bedroom suite

May 10 – 17

€ 96 per night
Guest favorite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Stunning farmhouse in historical village

Aug 20 – 27

€ 359 per night
Guest favorite

Guesthouse in Grafton

4.89 out of 5 average rating, 90 reviews

VT Sugar House-Guesthouse

Oct 22 – 29

€ 78 per night
Guest favorite

Tiny home in Chester

5.0 out of 5 average rating, 18 reviews

Zen of the Woods Tiny Cabin in Okemo Valley

May 3 – 10

€ 183 per night
Guest favorite

Farm stay in Baltimore

4.93 out of 5 average rating, 94 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

Apr 10 – 17

€ 117 per night
Guest favorite

Loft in Town of Rockingham

5.0 out of 5 average rating, 31 reviews

Saxtons River Studio apartment

Nov 28 – Dec 5

€ 120 per night
Guest favorite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Mountain Views, hiking, biking, 4 bedroom 6 acres

Apr 15 – 22

€ 429 per night
Guest favorite

Condo in Cavendish

5.0 out of 5 average rating, 20 reviews

One Bedroom Suite Near Okemo

Apr 20 – 27

€ 114 per night
Guest favorite

Cabin in Cavendish

4.88 out of 5 average rating, 17 reviews

Caretaker’s Cottage

Jun 13 – 20

€ 47 per night
Guest favorite

Cottage in Chester

4.93 out of 5 average rating, 59 reviews

Quaint stone house!

Sep 19 – 26

€ 229 per night
Guest favorite

Vacation home in Town of Rockingham

4.96 out of 5 average rating, 51 reviews

Cozy studio at Leslie's Tavern in Rockingham

Jul 14 – 21

€ 156 per night

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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Chester