Book Holiday Homes in Chester

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chester

Historic Charm, Located On the River - Rustic Chic

Historic Charm, Located On the River - Rustic Chic

Woodstock VT
Stay at this holiday home in Woodstock. Enjoy a garden, laundry facilities and balconies. Popular attractions Quechee Gorge Bridge and Taftsville Covered Bridge ...
Opens in a new windowHistoric Charm, Located On the River - Rustic Chic
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT
Stay at this holiday home in Cavendish. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Okemo Mountain Resort and ...
Opens in a new windowThe Dorothy-10 minutes from Okemo- freshly renovated
Okemo Mountain Lodging  by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
77 Okemo Ridge Rd Ludlow VT
Stay at this holiday home in Ludlow. Enjoy free parking, laundry facilities and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet ...
Opens in a new windowOkemo Mountain Lodging by Vail Resorts
Save an average of 15% on thousands of hotels when you're signed in
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT
Stay at this holiday home in Jamaica. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stratton Mountain Resort and Solstice Ski Lift are ...
Opens in a new windowStarry Skies: 7min to SkiStratton+PikesFalls+DogOK
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 VT
The price is NZ$573 per night from 19 May to 20 May
NZ$573
19 May - 20 May
includes taxes & fees
Stay at this holiday home in Ludlow. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Okemo Mountain Resort and Dorsey Park are located ...
Opens in a new windowGorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Manchester Center VT
Stay at this family-friendly holiday home in Manchester Center. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in ...
Opens in a new windowHistoric Renovated Barn at Boorn Brook Farm - Manchester Vermont
LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath 
Private Lake Views

LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views

Peru VT
Stay at this family-friendly holiday home in Peru. Enjoy free Wi-Fi, a fitness centre and a garden. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowLUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views
Sunlit VT Country Home w/Hot Tub.  Ideal location near Woodstock village

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Woodstock VT
Stay at this family-friendly holiday home in Woodstock. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Union Arena Community Center ...
Opens in a new windowSunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica VT
Stay at this holiday home in Jamaica. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Hot Glass Works and Ball Mountain State ...
Opens in a new windowPotter's Place | House in Jamaica with mountain views
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
966 Holiday Homes
Lowest Price
NZ$241
Highest Price
NZ$917
Popular accommodation
Historic Charm, Located On the River - Rustic Chic, The Dorothy-10 minutes from Okemo- freshly renovated, Okemo Mountain Lodging by Vail Resorts, Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont, LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views, Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village, Potter's Place | House in Jamaica with mountain views

Top trending hotels in Chester

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
The price is NZ$241 per night from 26 May to 27 May
NZ$241
26 May - 27 May
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
Opens in a new windowFullerton Inn
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Chester VT
The price is NZ$917 per night from 16 June to 17 June
NZ$917
16 June - 17 June
includes taxes & fees
Stay at this farm stay in Chester. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions DaVallia Art & Accents and Bonnie's Bundles Dolls ...
Opens in a new windowHistoric 150-year-old farmhouse, Jacuzzi included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$676 per night from 25 May to 26 May
NZ$676
25 May - 26 May
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowWoodstock Inn & Resort
Save an average of 15% on thousands of hotels when you're signed in
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is NZ$330 per night from 19 May to 20 May
NZ$330
19 May - 20 May
includes taxes & fees
Stay at this spa hotel in Cavendish. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowPointe at Castle Hill Resort
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.