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.

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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!

Nov 5 – 12

G$21,367 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 337 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Oct 23 – 30

G$21,066 GYD 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.

Feb 26 – Mar 5

G$19,035 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

May 12 – 19

G$19,473 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Sep 4 – 11

G$21,418 GYD per night

Guest favorite

Guest suite in Chester

4.91 out of 5 average rating, 155 reviews

Chester Carriage House-Cozy-Quintessential Vermont

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Jun 5 – 12

G$31,574 GYD per night

Guest favorite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Dec 9 – 16

G$25,567 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 318 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Nov 18 – 25

G$28,283 GYD per night

Guest favorite

Apartment in Chester

4.92 out of 5 average rating, 126 reviews

Lovely 2 Bedroom Apartment w/deck & pond view

The perfect Vermont getaway. Lovely new apartment behind retail store on main road to Okemo and Killington for winter skiing and summer adventure. Bedroom, living room, bunk room, fully equipped kitchen, laundry and mudroom. Large deck with pond view, easy access to vacation sites, mountain hiking and biking, discovering Vermont small towns. Experienced, welcoming Airbnb Super Hosts providing all the amenities for a comfortable stay.

Jan 24 – 31

G$39,445 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Aug 10 – 17

G$20,998 GYD per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 22 – 29

G$23,383 GYD per night

Guest favorite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

May 8 – 15

G$23,280 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chester vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Apartment in Springfield

4.91 out of 5 average rating, 222 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Jun 2 – 9

G$21,546 GYD per night

Guest favorite

Apartment in Claremont

4.88 out of 5 average rating, 110 reviews

Beautiful 1 bedroom apartment with balcony

Mar 1 – 8

G$18,146 GYD per night

Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 148 reviews

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

Aug 2 – 9

G$52,359 GYD per night

Guest favorite

Condo in Ludlow

4.99 out of 5 average rating, 100 reviews

Updated Main St Condo in downtown Ludlow!

Jun 4 – 11

G$23,291 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 588 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Oct 26 – Nov 2

G$28,384 GYD per night

Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 205 reviews

Sunset Cabin - your private romantic hideaway

Jul 22 – 29

G$32,371 GYD per night

Superhost

Apartment in Weston

4.86 out of 5 average rating, 128 reviews

Cozy Guesthouse in Heart of VT

Aug 5 – 12

G$20,052 GYD per night

Guest favorite

Home in Putney

4.95 out of 5 average rating, 307 reviews

Cozy Train Depot in Putney Vermont

May 13 – 20

G$20,122 GYD per night

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Other great vacation rentals in Chester

Guest favorite

Farm stay in Chester

4.98 out of 5 average rating, 40 reviews

Rivers Edge Farm’s Cozy Cabin

Aug 19 – 24

G$19,305 GYD per night

Guest favorite

Tiny home in Chester

5.0 out of 5 average rating, 82 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Aug 31 – Sep 7

G$53,271 GYD per night

Guest favorite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Private Home in Chester, VT

May 16 – 23

G$63,566 GYD per night

Guest favorite

Guesthouse in Grafton

4.89 out of 5 average rating, 91 reviews

VT Sugar House-Guesthouse

May 8 – 15

G$15,081 GYD per night

Guest favorite

Tiny home in Chester

5.0 out of 5 average rating, 19 reviews

Zen of the Woods Tiny Cabin in Okemo Valley

May 17 – 24

G$30,529 GYD per night

Guest favorite

Loft in Town of Rockingham

5.0 out of 5 average rating, 32 reviews

Saxtons River Studio apartment

Feb 16 – 23

G$23,897 GYD per night

Guest favorite

Home in West Windsor

4.96 out of 5 average rating, 55 reviews

Birdie's Nest Guesthouse

Jan 27 – Feb 3

G$28,380 GYD per night

Guest favorite

Vacation home in Town of Rockingham

4.96 out of 5 average rating, 53 reviews

Cozy studio at Leslie's Tavern in Rockingham

Sep 6 – 13

G$31,727 GYD per night

Show all

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
G$12,509 GYD 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.

Chester vacation rentals

Top-rated vacation rentals in Chester

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Other great vacation rentals in Chester

Apartment in Springfield

Apartment in Claremont

Tiny home in Athens

Condo in Ludlow

Guesthouse in Wallingford

Cabin in West Windsor

Apartment in Weston

Home in Putney

Other great vacation rentals in Chester

Farm stay in Chester

Tiny home in Chester

Home in Chester

Guesthouse in Grafton

Tiny home in Chester

Loft in Town of Rockingham

Home in West Windsor

Vacation home in Town of Rockingham

Quick stats about vacation rentals in Chester

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Chester?

Are there vacation rentals with a dedicated workspace in Chester?

How much does it cost to stay in house rentals in Chester?

Do house rentals in Chester have a bbq area?

Do house rentals in Chester have air conditioning?

Are there family-friendly house rentals in Chester?

Do house rentals in Chester have wireless internet?

What are the most popular amenities for House Rentals in Chester?

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