Chester Holiday Rentals

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Check prices for these dates

Tonight
1 Aug - 2 Aug
Tomorrow
2 Aug - 3 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Experience the airy atmosphere of this room with a high ceiling and large skylight, offering a view of the outdoors.

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
Situated in a serene evergreen forest, this cabin features a symmetrical design with a central chimney and large windows.

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (45)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort
Relax by the pool surrounded by lush trees and a distant church spire.

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 HK$2,437
HK$3,030 total
includes taxes & fees
6 Aug - 7 Aug
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Step up to a charming country retreat with a deck and comfortable seating area.

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (212)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Relax by the campfire in a serene wooded setting, surrounded by Adirondack chairs and a rustic picnic table.

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

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Cozy cabin retreat with a high ceiling, central fireplace, and comfortable seating area.

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

9.6 out of 10, Exceptional, (25)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Quaint lakefront home with a fire pit and beautiful views
Enjoy breathtaking views of the snowy landscape from this deck overlooking the serene surroundings.

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
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Enjoy cooking in this well-equipped kitchen with a wooden dining table and chairs.

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (39)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cozy space with a high ceiling, round table, and four chairs, surrounded by large windows and a decorative wreath.

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

9.6 out of 10, Exceptional, (225)
"Very cozy cabin for a weekend getaway. Multiple fireplaces with plenty of firewood available. Great place to curl up with a book or lots of shopping / restaurants in the area. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Cozy cabin-style bedroom with a wood-burning stove, stone wall, and comfortable seating area.

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
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cozy cabin interior with a dining area, wooden dining table, and comfortable sofa.

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

10.0 out of 10, Exceptional, (18)
"Thanks for a great stay!"
The price is HK$1,405
HK$2,479 total
includes taxes & fees
11 Aug - 12 Aug
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Fully equipped kitchen with stainless steel appliances, dark cabinets, and a white tiled backsplash.

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Situated amidst a serene landscape, this charming house features a covered porch, a chimney, and a small front porch with a bench.

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (158)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is HK$1,334
HK$2,875 total
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Solitude Village at Okemo
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, toaster, and oven.

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (26)
"Beautiful Area. "
Solitude Village at Okemo
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Escape to a serene cabin retreat surrounded by trees and a seasonal touch.

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
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Stunning two-story house with a steeply pitched roof and inviting front porch, set amidst a beautifully manicured lawn and lush garden.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (218)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Relax in a serene hot tub surrounded by a wooded area and a wooden deck.

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is HK$1,589
HK$5,055 total
includes taxes & fees
17 Aug - 18 Aug
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Treehouse at Wise Pines- NoBo
Escape to a serene forest retreat with a cozy cabin featuring a balcony and hammock nestled among the trees.

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is HK$1,295
HK$1,623 total
includes taxes & fees
8 Aug - 9 Aug
Treehouse at Wise Pines- NoBo
The Mountain Escape!
Relax in a hot tub on a snow-covered deck.

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is HK$1,662
HK$5,372 total
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Relax in this serene bedroom with a large bed, nightstand, and dresser, surrounded by natural light and large windows.

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.6 out of 10, Exceptional, (11)
"Excellent location"
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
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 2 days ago
The Covered Bridge Inn

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to DaVallia Art & Accents, or you can select a more secluded option if you're looking for 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 coffee shops and restaurants.

What are some of the best holiday rentals that Chester has to offer?

Quaint lakefront home with a private deck, firepit, and dock: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Chester?

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

What’s there to see and do in Chester?

DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of the family-friendly sights. Vermont Museum of Mining and Minerals and Vermont Country Store are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals feature extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.