Vacation Homes in Chester
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Featured Vacation Homes in Chester

New Ludlow Village Home with Stunning Okemo Mountain View

☆ SKI ON/OFF! ☆ 2BR+ Trailside! Hot tub, pool, gym +more

The Dorothy-10 minutes from Okemo- freshly renovated

3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Shuttle or walk to village and lifts! Hot Tub + More!

Fabulous 4-bedroom house in Ludlow perfect for your ski getaway

Escape to Shadow Peak Retreat: Your Luxurious Vermont Getaway

Beautiful Waterfront , four season home on charming Crescent Lake!

Okemo Mountain Lodging by Vail Resorts

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Top trending hotels in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Vacation Rentals in Chester
What kind of vacation do you want in Chester? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Chester that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Chester, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Chester Vacation Homes essential information
Accommodation | 873 Vacation Homes |
|---|---|
Lowest Price | CA $133 |
Highest Price | CA $1,473 |
Popular accommodation | New Ludlow Village Home with Stunning Okemo Mountain View, ☆ SKI ON/OFF! ☆ 2BR+ Trailside! Hot tub, pool, gym +more, The Dorothy-10 minutes from Okemo- freshly renovated, 3 Levels w/ Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, ACs, Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Shuttle or walk to village and lifts! Hot Tub + More!, Fabulous 4-bedroom house in Ludlow perfect for your ski getaway, Escape to Shadow Peak Retreat: Your Luxurious Vermont Getaway, Beautiful Waterfront , four season home on charming Crescent Lake!, Okemo Mountain Lodging by Vail Resorts, Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!! |





