Chester Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chester holiday rentals

Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is HK$4,219
HK$7,828 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Vermont Cabin · Mountain Views · Near Okemo
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is HK$1,626
HK$3,327 total
includes taxes & fees
29 Mar - 30 Mar
Charming Chester Farmhouse near Near VT Slopes
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (20 reviews)
"Amazing place, cozy, clean and organized. I loved it and I want to come back again."
United States
Alex F.
The price is HK$2,150
HK$2,562 total
includes taxes & fees
13 Apr - 14 Apr
Owl's Nest Treehouse
Outdoor spa tub

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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,537
HK$3,154 total
includes taxes & fees
19 Apr - 20 Apr
Long Trail House at Stratton Mountain Resort
Exterior

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, (168 reviews)
"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 HK$1,329
HK$2,758 total
includes taxes & fees
31 Mar - 1 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (21 reviews)
"The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "
United States
Ashley P.
The price is HK$1,407
HK$2,927 total
includes taxes & fees
1 Apr - 2 Apr
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Interior

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is HK$1,759
HK$4,497 total
includes taxes & fees
28 Mar - 29 Mar
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is HK$1,173
HK$1,471 total
includes taxes & fees
1 Apr - 2 Apr
Treehouse at Wise Pines- NoBo
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Amazing place! "
United States
Tara
The price is HK$2,345
HK$4,212 total
includes taxes & fees
28 Mar - 29 Mar
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,252
HK$4,648 total
includes taxes & fees
30 Mar - 31 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,611
HK$1,986 total
includes taxes & fees
29 Mar - 30 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is HK$1,740
HK$3,512 total
includes taxes & fees
30 Mar - 31 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is HK$1,761
HK$3,545 total
includes taxes & fees
31 Mar - 1 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is HK$1,471
HK$5,010 total
includes taxes & fees
1 Apr - 2 Apr
Romantic Riverbed Treehouse - hot tub & new sauna!
Exterior

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is HK$1,055
HK$2,005 total
includes taxes & fees
31 Mar - 1 Apr
Wellness Getaway with a Personal Sauna, and Private River Beach!
Property grounds

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4 reviews)
"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$844
HK$2,698 total
includes taxes & fees
31 Mar - 1 Apr
Lake Front Family Friendly Escape
Exterior

Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is HK$3,096
HK$6,855 total
includes taxes & fees
30 Mar - 31 Mar
Insanely romantic treehouse perched next to a stream and rolling hills.
Outdoor spa tub

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.
Killington
9.6 out of 10, Exceptional, (72 reviews)
"Amazing ski-in/out property slope-side! We enjoyed our stay very much! "
United States
Jason
Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is HK$1,409
HK$4,224 total
includes taxes & fees
26 Apr - 27 Apr
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Indoor pool

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Okemo Village
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time , the location was amazing and the owner responded very quickly for any questions or concerns "
United States
Thomas B.
The price is HK$1,759
HK$4,099 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"There's a cute little town nearby with a great coffee shop. "
Brendan 2-night trip
Posted 19 hours ago
Pointe at Castle Hill Resort

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 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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: 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 12 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chester?

Choose from 36 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.