Chester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Chester

Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Vacation Home in Chester

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is ￥84,197
￥157,797 total
includes taxes & fees
Dec 2 - Dec 3
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior
Whimsical Room & Private Bathroom in Historic Inn

Vacation Home in Chester Depot

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is ￥20,147
￥31,661 total
includes taxes & fees
Dec 2 - Dec 3
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Vacation Home in Chester Depot

9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is ￥23,271
￥54,401 total
includes taxes & fees
Dec 2 - Dec 3
Chester Farmhouse Ski Retreat near Slopes
Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is ￥6,072
￥39,865 total
includes taxes & fees
Dec 8 - Dec 9
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is ￥58,606
￥72,849 total
includes taxes & fees
Dec 8 - Dec 9
Long Trail House at Stratton Mountain Resort
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is ￥21,084
￥39,707 total
includes taxes & fees
Dec 5 - Dec 6
Wellness Getaway with a Personal Sauna, and Private River Beach!
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Cottage in Ludlow

3.0 star property
The price is ￥31,705
￥60,620 total
includes taxes & fees
Dec 2 - Dec 3
Ludlow Ski Cabin 2 Mi to Ski Parking
Smart TV, fireplace, books
Private cabin: 7 mins to slopes, wood fireplace

Chalet in Dover

2.0 star property
9.6 out of 10, Exceptional, (5)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is ￥60,910
￥130,421 total
includes taxes & fees
Dec 2 - Dec 3
Private cabin: 7 mins to slopes, wood fireplace
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

2.0 star property
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ￥29,830
￥51,595 total
includes taxes & fees
Dec 2 - Dec 3
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Chalet in Plymouth

2.0 star property
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is ￥28,253
￥85,345 total
includes taxes & fees
Dec 7 - Dec 8
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥31,962
￥39,085 total
includes taxes & fees
Dec 2 - Dec 3
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is ￥42,950
￥53,380 total
includes taxes & fees
Dec 3 - Dec 4
Owl's Nest Treehouse
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Apartment in Bromley Mountain

9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
The price is ￥14,156
￥50,774 total
includes taxes & fees
Dec 10 - Dec 11
Cozy Bromley Retreat
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin in Londonderry

2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is ￥23,193
￥56,919 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Exterior
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
The price is ￥23,427
￥29,209 total
includes taxes & fees
Dec 2 - Dec 3
Treehouse at Wise Pines- NoBo
Golf
Efficient condo near slopes with kitchenette & great location

Apartment in Ludlow

8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is ￥14,837
￥35,467 total
includes taxes & fees
Dec 2 - Dec 3
Efficient condo near slopes with kitchenette & great location
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Condo in Clock Tower Base Area

9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥12,338
￥40,661 total
includes taxes & fees
Dec 8 - Dec 9
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV, fireplace
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Condo in Stratton

8.6 out of 10, Excellent, (27)
"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 ￥11,245
￥43,830 total
includes taxes & fees
Dec 2 - Dec 3
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Iron/ironing board, WiFi, bed sheets
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Apartment in Bridgewater

10.0 out of 10, Exceptional, (5)
"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 ￥12,494
￥30,234 total
includes taxes & fees
Dec 2 - Dec 3
Woodstock Suite | 10 Min to Mountains |A/C| Hiking
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Cabin in Grafton

9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is ￥26,551
￥57,200 total
includes taxes & fees
Dec 15 - Dec 16
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good. "
William 2-night trip
Posted 6 hours ago
Jackson Gore Village

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chester!

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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home rental near Chester is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals will I find in Chester?

Choose from 34 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. Stratton Mountain Resort and Grafton Historical Society 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.