Chester Apartments
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 Apartments in Chester
Long Trail House Studio at Stratton Mountain Resort
Stratton VT
When you stay at this apartment in Stratton, you'll be in the mountains, within a 5-minute walk of Stratton Mountain Resort and Green Mountain National ...
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Stratton VT
When you stay at this apartment in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
Deluxe Studio | Murphy Bed + Sofa
West Dover VT
The price is AU$705 per night from 22 Dec to 23 Dec
AU$705
22 Dec - 23 Dec
includes taxes & fees
When you stay at this apartment in West Dover, you'll be in the mountains, within a 5-minute walk of Mount Snow and Green Mountain National Forest.
Save an average of 15% on thousands of hotels when you're signed in
Efficient condo near slopes with kitchenette & great location
Ludlow VT
The price is AU$427 per night from 5 Jan to 6 Jan
AU$427
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this apartment, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Dorsey Park.
Let it Snow-Perfect Getaway! Cozy, Modern & convenience to everything!
Ludlow VT
With a stay at this apartment in Ludlow, you'll be in the mountains, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park.
Hawks Mountain Farm, full apartment on a working farm.
Baltimore VT
Located in Chester, this apartment is in the mountains, within a 15-minute drive of Springfield Art and Historical Society Museum and Stoughton Pond Recreation ...
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Ludlow VT
With a stay at this apartment, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park.
Nana's House
Bridgewater VT
Located in Bridgewater, this apartment is on a river, within a 15-minute drive of Long Trail Brewing Company and Union Arena Community Center.
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
Bridgewater VT
With a stay at this apartment in Bridgewater Corners, you'll be on a river, within a 5-minute drive of Killington Resort and Skyeship Express Gondola Stage ...
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 Apartments essential information
Accommodation | 174 Apartments |
|---|---|
Lowest Price | AU$291 |
Highest Price | AU$705 |
Popular accommodation | Long Trail House Studio at Stratton Mountain Resort, Stratton South Long Trail Studio Adjacent to the Village and Lifts, Deluxe Studio | Murphy Bed + Sofa, Efficient condo near slopes with kitchenette & great location, Let it Snow-Perfect Getaway! Cozy, Modern & convenience to everything!, Hawks Mountain Farm, full apartment on a working farm., Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly, Nana's House, Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily |
Top trending hotels in Chester
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is AU$597 per night from 19 Jan to 20 Jan
AU$597
19 Jan - 20 Jan 2026
includes taxes & fees
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is AU$291 per night from 4 Jan to 5 Jan
AU$291
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
Save an average of 15% on thousands of hotels when you're signed in
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
The price is AU$518 per night from 1 Jan to 2 Jan
AU$518
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at The Equinox Golf Resort & Spa in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and Golf ...
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.
More ways to explore Chester
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.