Chester Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Chester holiday rentals

Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is S$672
includes taxes & fees
1 Apr - 2 Apr
Outdoor Adventure Hub! Family Home in West Dover
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 S$525
includes taxes & fees
15 Apr - 16 Apr
Long Trail House at Stratton Mountain Resort
Exterior

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts
3.5 star property
Clock Tower Base Area
7.8 out of 10, Good, (28 reviews)
"I had an amazing time with my family, I will definitely be coming back "
United States
Yenifer
The price is S$2,458
includes taxes & fees
1 Apr - 2 Apr
Okemo Mountain Lodging by Vail Resorts
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 S$741
includes taxes & fees
8 Apr - 9 Apr
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is S$2,038
includes taxes & fees
1 May - 2 May
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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

8/10 Good
"Have stayed here many times. Close to town and Okemo. Very convenient."
Richard 2-night trip
Posted 19 hours ago
Pointe at Castle Hill Resort

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.

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.