Chester Vacation Rentals

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Check prices for these dates

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Aug 13 - Aug 14
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Aug 14 - Aug 15
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Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Interior

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Solitude Village at Okemo
Solitude Village Two Bedroom Suite Mountainside | Private kitchen | Fridge, microwave, stovetop, toaster

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very Good, (26)
"Beautiful Area. "
Solitude Village at Okemo
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
TV, fireplace, video games

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

9.4 out of 10, Exceptional, (26)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
3 bedrooms, internet, bed sheets

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (26)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Dining

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (226)
"Beautiful little cabin, very nice location quiet and secluded. Easy access to main road near to town."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is ￥47,652
￥59,233 total
includes taxes & fees
Aug 19 - Aug 20
Long Trail House at Stratton Mountain Resort
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (174)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Treehouse at Wise Pines- SoBo
Property grounds

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is ￥24,296
￥30,276 total
includes taxes & fees
Aug 17 - Aug 18
Treehouse at Wise Pines- SoBo
Treehouse at Wise Pines- NoBo
Exterior

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is ￥24,296
￥30,441 total
includes taxes & fees
Aug 22 - Aug 23
Treehouse at Wise Pines- NoBo
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

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

10.0 out of 10, Exceptional, (5)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is ￥29,262
￥50,148 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Interior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is ￥48,372
￥83,448 total
includes taxes & fees
Aug 20 - Aug 21
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

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

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is ￥11,044
￥37,464 total
includes taxes & fees
Aug 18 - Aug 19
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (53)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Quaint lakefront home with a fire pit and beautiful views
Property grounds

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (54)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, foosball, table tennis

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (51)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
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

The Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"All good"
richard 1-night trip
Posted 1 day ago
The Covered Bridge Inn

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?

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond: This vacation home near Chester is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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. Grafton Historical Society and Vermont Country Store 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.