Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (20 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is CA $272
CA $567 total
includes taxes & fees
May 21 - May 22
Charming Chester Farmhouse near Near VT Slopes

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is CA $417
CA $662 total
includes taxes & fees
May 19 - May 20
LUXE Forest Retreat

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is CA $309
CA $788 total
includes taxes & fees
May 19 - May 20
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Brand New Luxury “Tiny” House, Immersed In Nature

Brand New Luxury “Tiny” House, Immersed In Nature
Athens
10.0 out of 10, Exceptional, (1 review)
"This is by far the most beautiful home I’ve ever stayed! So clean and amazing views of nature. We can’t wait to come back."
United States
Mia G.
The price is CA $378
CA $613 total
includes taxes & fees
May 19 - May 20
Brand New Luxury “Tiny” House, Immersed In Nature

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $741
CA $1,389 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Vermont Cabin · Mountain Views · Near Okemo

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (12 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is CA $234
CA $508 total
includes taxes & fees
May 20 - May 21
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (80 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
The price is CA $103
CA $357 total
includes taxes & fees
May 19 - May 20
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $67
CA $306 total
includes taxes & fees
May 19 - May 20
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (18 reviews)
"It was an amazing experience! "
United States
Gruha
The price is CA $217
CA $398 total
includes taxes & fees
May 19 - May 20
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
JAMAICA
10.0 out of 10, Exceptional, (1 review)
"Had a great couple days at the "glamping cabin." The ride to get there on a dark foggy night was a bit thrilling, but could immediately relax once I got into the cabin. Place has everything needed for a semi-primitive cabin experience. Enjoyed the sauna and thencozy bed. "
United States
Brittney C.
The price is CA $96
CA $218 total
includes taxes & fees
May 25 - May 26
Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is CA $94
CA $448 total
includes taxes & fees
May 24 - May 25
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is CA $234
CA $414 total
includes taxes & fees
May 25 - May 26
Wellness Getaway with a Personal Sauna, and Private River Beach!

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is CA $109
CA $265 total
includes taxes & fees
May 20 - May 21
Vermont Suite | 10 Min to Woodstock & Killington

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is CA $378
CA $464 total
includes taxes & fees
Jun 1 - Jun 2
Owl's Nest Treehouse

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is CA $103
CA $339 total
includes taxes & fees
May 26 - May 27
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is CA $183
CA $374 total
includes taxes & fees
May 20 - May 21
The Studio with a View. Bring your dog, too!

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is CA $117
CA $280 total
includes taxes & fees
May 31 - Jun 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (35 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is CA $98
CA $424 total
includes taxes & fees
May 19 - May 20
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is CA $125
CA $450 total
includes taxes & fees
May 19 - May 20
Cozy Bromley Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near DaVallia Art & Accents, or you can select a more remote option if you want a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffeehouses and restaurants.

What are some of the best vacation rentals in Chester?

Mountainside 5-BR Ski-In/Out Okemo Villa: This vacation home near Chester is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals will I find in Chester?

Choose from 32 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of family-friendly sights. Vermont Country Store and Lowell Lake State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.