Chester Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Chester

Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

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 HK$622
HK$1,132 total
includes taxes & fees
20 Nov - 21 Nov
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

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 HK$1,158
HK$2,708 total
includes taxes & fees
23 Nov - 24 Nov
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo

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 HK$4,191
HK$7,750 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior
Ben & Jerry Suite | Skiing | Hiking | Biking

Ben & Jerry Suite | Skiing | Hiking | Biking

Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is HK$622
HK$1,505 total
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking
Property grounds
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, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$622
HK$2,024 total
includes taxes & fees
23 Nov - 24 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$599
HK$2,256 total
includes taxes & fees
23 Nov - 24 Nov
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
TV, DVD player
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, (25)
"Loved the location"
United States
Steven W.
The price is HK$529
HK$1,895 total
includes taxes & fees
2 Dec - 3 Dec
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is HK$972
HK$1,977 total
includes taxes & fees
24 Nov - 25 Nov
Family Friendly Hilltop House In Putney Vermont
Pool
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is HK$2,343
HK$2,912 total
includes taxes & fees
20 Nov - 21 Nov
Long Trail House at Stratton Mountain Resort
Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ludlow
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is HK$1,081
HK$2,250 total
includes taxes & fees
20 Nov - 21 Nov
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Interior
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ludlow
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is HK$614
HK$1,812 total
includes taxes & fees
2 Dec - 3 Dec
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

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

2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,050
HK$1,977 total
includes taxes & fees
1 Dec - 2 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Cozy Bromley Retreat

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 HK$705
HK$2,527 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Bromley Retreat
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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

2.0 star property
Cavendish
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 HK$1,360
HK$2,403 total
includes taxes & fees
20 Nov - 21 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior detail
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is HK$614
HK$1,812 total
includes taxes & fees
2 Dec - 3 Dec
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Fridge, microwave, oven, stovetop
Lake Front Family Friendly Escape

Lake Front Family Friendly Escape

Newport
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is HK$980
HK$2,893 total
includes taxes & fees
2 Dec - 3 Dec
Lake Front Family Friendly Escape
Microwave, oven, stovetop, coffee/tea maker
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Ludlow
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
The price is HK$614
HK$2,015 total
includes taxes & fees
2 Dec - 3 Dec
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Golf
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

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 HK$614
HK$1,590 total
includes taxes & fees
1 Dec - 2 Dec
Efficient condo near slopes with kitchenette & great location
Beach
Pet-friendly winter retreat in the woods near Okemo + Killington

Pet-friendly winter retreat in the woods near Okemo + Killington

2.0 star property
Plymouth
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 HK$1,392
HK$3,492 total
includes taxes & fees
20 Nov - 21 Nov
Pet-friendly winter retreat in the woods near Okemo + Killington
Internet, bed sheets
Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow
8.8 out of 10, Excellent, (29)
"Great location and great place!"
United States
Linda G.
The price is HK$614
HK$1,664 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Condo with Great Location, WiFi & Kitchenette
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

Mountaineer Inn

Mountaineer Inn

10/10 Excellent
"Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again "
Joseph 1-night trip
Posted 15 hours ago
Mountaineer Inn

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:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

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

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Bonnie's Bundles Dolls, 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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Chester?

Choose from 34 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of the family-friendly sights. Stratton Mountain Resort 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.