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

Home in Weston

4.95 out of 5 average rating, 226 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

May 30 – Jun 6

G$28,230 GYD 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!

Aug 21 – 28

G$21,784 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.

Mar 14 – 21

G$19,079 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 492 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.

May 31 – Jun 7

G$20,773 GYD per night

Guest favorite

Home in Ludlow

4.92 out of 5 average rating, 139 reviews

149 Upper Crossroad Unit A

Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps 8 and has been beautifully appointed, with 2 Family rooms, 3 bedrooms, 2 bathrooms, a large open concept Kitchen, and Dining room with Gas Stove. The kitchen boasts granite countertops, dishwasher, with essentials. A short 5-minute walk to the Okemo Clock Tower Base Lodge, or a weekend/holiday shuttle that stops at the home for those who prefer not to walk it.

Nov 4 – 11

G$20,755 GYD per night

Guest favorite

Guest suite in Chester

4.92 out of 5 average rating, 154 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!

Jul 21 – 28

G$30,359 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.

Sep 4 – 11

G$25,626 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 316 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 13 – 20

G$28,318 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 23 – 30

G$39,537 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 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.

May 3 – 10

G$20,467 GYD 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

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Apr 22 – 29

G$32,615 GYD per night

Guest favorite

Apartment in Claremont

4.88 out of 5 average rating, 110 reviews

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

Jul 15 – 22

G$18,188 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

Apr 30 – May 7

G$20,983 GYD per night

Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 147 reviews

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

Jan 27 – Feb 3

G$52,480 GYD per night

Superhost

Condo in Ludlow

4.92 out of 5 average rating, 121 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

May 19 – 26

G$23,045 GYD per night

Superhost

Apartment in Weston

4.86 out of 5 average rating, 128 reviews

Cozy Guesthouse in Heart of VT

Jul 27 – Aug 3

G$21,134 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 334 reviews

Vermont Botanical Studio Apartment

Jan 20 – 27

G$24,079 GYD per night

Guest favorite

Home in S Londonderry

4.95 out of 5 average rating, 270 reviews

Cozy barn apartment in So. Vermont

Mar 5 – 12

G$30,615 GYD per night

Guest favorite

Home in Weston

4.86 out of 5 average rating, 106 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

Sep 29 – Oct 6

G$26,453 GYD per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Jan 24 – 31

G$26,485 GYD per night

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Other great vacation rentals in Chester

Guest favorite

Home in Chester

4.9 out of 5 average rating, 10 reviews

Charming Chester Farmhouse

Jun 22 – 29

G$59,049 GYD per night

Superhost

Vacation home in Cavendish

4.84 out of 5 average rating, 32 reviews

Cozy 1 bd Apt Minutes to Okemo & Pet Friendly

May 29 – Jun 5

G$17,988 GYD per night

Guest favorite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Private Home in Chester, VT

Dec 20 – 27

G$67,485 GYD per night

Guest favorite

Cottage in Chester

4.92 out of 5 average rating, 60 reviews

Quaint stone house!

Mar 30 – Apr 6

G$43,758 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$15,116 GYD per night

Guest favorite

Loft in Town of Rockingham

5.0 out of 5 average rating, 32 reviews

Saxtons River Studio apartment

Nov 26 – Dec 3

G$23,952 GYD per night

Guest favorite

Farm stay in Baltimore

4.92 out of 5 average rating, 96 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

Jun 22 – 29

G$23,819 GYD per night

Guest favorite

Home in Chester

4.93 out of 5 average rating, 28 reviews

Stunning farmhouse in historical village

Oct 4 – 11

G$74,060 GYD per night

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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$12,538 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 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.

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

Tiny home in Athens

Condo in Ludlow

Apartment in Weston

Home in Putney

Home in S Londonderry

Home in Weston

Home in Chester

Other great vacation rentals in Chester

Home in Chester

Vacation home in Cavendish

Home in Chester

Cottage in Chester

Guesthouse in Grafton

Loft in Town of Rockingham

Farm stay in Baltimore

Home in Chester

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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