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Chester Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chester holiday rentals

Dining

1. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is HK$1,639
HK$3,311 total
includes taxes & fees
8 Nov - 9 Nov
Charming Chester Farmhouse near Near VT Slopes
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is HK$2,196
HK$5,516 total
includes taxes & fees
5 Nov - 6 Nov
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story house with a deck, surrounded by dense forest.

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,228
HK$7,845 total
includes taxes & fees
6 Nov - 7 Nov
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

4. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
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 HK$404
HK$1,820 total
includes taxes & fees
2 Nov - 3 Nov
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A red house with a covered porch and a chimney.

5. 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, (174 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
The price is HK$1,333
HK$2,872 total
includes taxes & fees
29 Oct - 30 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A building with multiple floors, a red curved structure, and a flower bed with purple flowers.

6. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is HK$585
HK$2,088 total
includes taxes & fees
2 Nov - 3 Nov
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

7. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (14 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is HK$883
HK$1,390 total
includes taxes & fees
3 Nov - 4 Nov
Fat Sheep Farm & Cabins
A two-story house with a porch, a staircase, and a front door.

8. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is HK$782
HK$2,421 total
includes taxes & fees
6 Nov - 7 Nov
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A two-story house with a covered porch, a staircase, and a front door with a wreath.

9. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is HK$782
HK$1,819 total
includes taxes & fees
6 Nov - 7 Nov
Compact downtown studio condo with kitchenette near the Okemo slopes
A two-story house with a porch, a staircase, and a front door.

10. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is HK$823
HK$2,129 total
includes taxes & fees
6 Nov - 7 Nov
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A two-story house with a porch, a staircase, and a front door.

11. Downtown studio with kitchenette, shuttle stop right across the street

Downtown studio with kitchenette, shuttle stop right across the street
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is HK$782
HK$1,872 total
includes taxes & fees
6 Nov - 7 Nov
Downtown studio with kitchenette, shuttle stop right across the street
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

12. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is HK$1,094
HK$2,149 total
includes taxes & fees
29 Oct - 30 Oct
Cozy cabin in charming Londonderry
A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

13. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
The price is HK$1,165
HK$2,876 total
includes taxes & fees
28 Oct - 29 Oct
Beautiful country cabin with hot tub and outdoor shower in Londonderry
A two-story house with a covered porch, a staircase, and a front door with a wreath.

14. First-floor downtown condo, less than a mile from Okemo Mountain

First-floor downtown condo, less than a mile from Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
The price is HK$1,029
HK$2,534 total
includes taxes & fees
28 Oct - 29 Oct
First-floor downtown condo, less than a mile from Okemo Mountain
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

15. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is HK$585
HK$2,008 total
includes taxes & fees
2 Nov - 3 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A wooden cabin interior with a staircase, a sofa, and a table.

16. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"A very clean and modern cabin. Loved the amenities like the paddle boards, kayaks and hot tub.!"
United States
Katherine B.
The price is HK$1,561
HK$3,186 total
includes taxes & fees
18 Nov - 19 Nov
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

17. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,460 total
includes taxes & fees
28 Oct - 29 Oct
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
A modern living room with a fireplace, a dining area, and a kitchen in the background.

18. Building C ground-floor ski-in/ski-out condo with Clock Tower views

Building C ground-floor ski-in/ski-out condo with Clock Tower views
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
The price is HK$1,235
HK$3,224 total
includes taxes & fees
9 Nov - 10 Nov
Building C ground-floor ski-in/ski-out condo with Clock Tower views
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

19. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is HK$663
HK$1,145 total
includes taxes & fees
28 Oct - 29 Oct
Yurt Oasis in the woods of Hinsdale, NH
A large house with a fire pit and outdoor seating.

20. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is HK$784
HK$1,616 total
includes taxes & fees
9 Nov - 10 Nov
Bridgewater Living - Ben&Jerry Suite
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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"We enjoyed our stay at The Shire. We chose a room with a river view, so we were located in a nicely restored house located right next to the main Inn. Our room was very spacious, clean and comfortable. The location was perfect for walking into town, and a quick drive to the Marsh-Billings-Rockefeller National Historic Park."
Judy 1-night trip
Posted 12 hours ago
The Shire Woodstock

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 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?

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 31 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 Country Store and Lowell Lake State Park 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.