Search Holiday Rentals in Chester

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Chester holiday rentals

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 10.605.330 ₫
13.182.426 ₫ total
includes taxes & fees
23 Mar - 24 Mar
Long Trail House at Stratton Mountain Resort
Condo, 4 Bedrooms | Sauna

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
The price is 17.328.062 ₫
36.086.265 ₫ total
includes taxes & fees
5 Mar - 6 Mar
Sunrise Bear Ridge C4 4 Bedroom Condo
House (5 Bedrooms) | Interior

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is 28.700.868 ₫
44.637.540 ₫ total
includes taxes & fees
8 Mar - 9 Mar
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Simple rooms, but it was clean and staff was friendly. Good for the price"
Christophe 2-night trip
Posted 4 days ago
Comfort Inn & Suites Brattleboro I-91

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.

How many holiday rentals will I find in Chester?

Choose from 35 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. While in the area, you can also visit popular places such as Okemo Mountain Resort and Stratton Mountain Resort.

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.