Search Apartments in Chester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 117 Apartments in Chester with updated reviews, rates, and availability.

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Exterior
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
10.0 out of 10, Exceptional, (4)
"We adored this place! Such a peaceful getaway while still close to town. We (stupidly) did not save the access instructions which was only an issue as there is no cell service while there. Thankfully I was able to pull up the email anyways but just a heads up for those visiting! Would 110% come back!"
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Well-appointed studio right downtown - less than a mile to Okemo Mountain
9.2 out of 10, Wonderful, (7)
"The room was exactly as advertised, small but nicely done, updated and the kitchen was well stocked. Great accommodations and super close to Okemo."
The price is AED 191
AED 893 total
includes taxes & fees
25 Sep - 26 Sep
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Cozy Studio Condo with Great Location, WiFi & Kitchenette
8.8 out of 10, Excellent, (23)
"Conveniently located within a 5 min. drive to Okemo Mountain Resort and within walking distance of a number of restaurant/bars. Has all the necessities for a weekend in Ludlow."
The price is AED 224
AED 700 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Hawks Mountain Farm, full apartment on a working farm.
Hawk Mountain Farm
Hawks Mountain Farm, full apartment on a working farm.
9.8 out of 10, Exceptional, (26)
"The apartment is clean, cozy and welcoming. Set on an out of the way road, but close to Springfield. The property is beautiful. David and Carol and great hosts. We got the farm tour, and met the donkeys, yaks, grass and chickens. We will be back! "
Hawks Mountain Farm, full apartment on a working farm.
New! Charming 1BR Hideaway in Hartland VT!
New! Charming 1BR Hideaway in Hartland VT!
6.0 out of 10, (1)
"apartment itself was good for what we needed but unfortunately the check in process was horrendous. the address listed was incorrect and dropped us in the middle of two roads. when we called multiple times for customer service and field service representatives were very unhelpful with the situation. It would have been helpful to be able to speak with the actual owner of the property. "
New! Charming 1BR Hideaway in Hartland VT!
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
Exterior
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
9.8 out of 10, Exceptional, (11)
"Bob was an incredible host and very responsive! This was a perfect getaway for me and the property was great. I'd stay again in a heartbeat. Thanks Bob for the great stay!"
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Living area
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
8.8 out of 10, Excellent, (5)
"This property is fine, but you should understand it’s not in the base area of Killington. I guess we did not read the fine print close enough or maybe it wasn’t included. This is a standalone property on a little hilltop a short drive to the extension gondola area, not at the base of Killington. One major issue is that the owner should replaced the mattress in the queen bed in the second room. It’s way too saggy other than that the property is fine clean and easy to."
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.2 out of 10, Wonderful, (23)
"Great space, very clean and cozy! We enjoyed the neighborhood, the cleanliness, and the peace and quiet we wanted to disconnect from the busy daily life. Would stay again 10/10! "
The price is AED 397
AED 1,066 total
includes taxes & fees
22 Sep - 23 Sep
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Queen sized bed, extra blankets, Roku TV and plenty of locally inspired charm.
Minutes to Woodstock | Hiking | Ben & Jerry Suite
9.6 out of 10, Exceptional, (4)
"Older building on the outside and yard. But rooms were remodeled and very nice. No contact with any staff except by text and emails. They give you a code for the doors. A little different."
The price is AED 459
AED 904 total
includes taxes & fees
22 Oct - 23 Oct
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
#68 Pleasant Street Ludlow ,Vt.
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
9.8 out of 10, Exceptional, (160)
"Helpful, as I am hoping to land on my feet"
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!
Manchester Center Vacation Rental | 1BR | 1BA | 2,000 Sq Ft | Stairs Required
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!
10.0 out of 10, Exceptional, (32)
"We loved staying at this cozy barn! The beds are so comfortable and the location was ideal! Will definitely be coming back for a longer stay! Highly recommend!"
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!
Okemo | Spacious Executive Room w Amenities Nearby
Immerse in breathtaking scenery at this location.
Okemo | Spacious Executive Room w Amenities Nearby
Okemo | Spacious Executive Room w Amenities Nearby
Cozy private apartment with winter views of Mt Equinox
Dining
Cozy private apartment with winter views of Mt Equinox
10.0 out of 10, Exceptional, (16)
"First time traveling East & we picked a perfect spot to stay. Plenty of room for myself & husband. Great kitchen & kitchen ware for meals. We especially enjoyed the deck outside. Good location to town, that we walked & explored around town. Bed was comfortable as well as having plenty of seating room. Easy check in process & communication."
Cozy private apartment with winter views of Mt Equinox
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Living area
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
10.0 out of 10, Exceptional, (2)
"We had a great weekend staying in this wonderful little vrbo. A great surprise was a general store that had everything we needed right across the street, and beautiful hiking and places to eat within a half hour. I also appreciated the updated and very comfortable king size mattress and bed! Hosts were very accommodating and had great communication. We would definitely stay here again."
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Comfortable Dover Apartment: Walk to Mt Snow!
Living area
Comfortable Dover Apartment: Walk to Mt Snow!
3.0 star property
9.0 out of 10, Wonderful, (2)
Comfortable Dover Apartment: Walk to Mt Snow!
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Living area
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
3.0 star property
10.0 out of 10, Exceptional, (1)
"I decided to stay a bit out of town for a ski trip....and it was perfect. Just a 10 min ride down the hill to OKEMO and LUDLOW. It is absolutely beautiful and quiet...the sunsets and sunrises are amazing from the top of that hill. It is secluded and you really get a slice of VT. The unit is very large and spacious. It has everything you need for a short stay...for some, not having a microwave is an issue, but not for me. Toaster over, full stove, fridge, electric water kettle, coffee maker,...
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
Terrace/patio
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
3.0 star property
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Ludlow Vacation Rental | Studio | 1BA | Step-Free Entry | 1,100 Sq Ft
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
10.0 out of 10, Exceptional, (3)
"Place was much bigger than expected, perfect set up for what we needed. Tons of privacy and great communication by the owner."
Charming Ludlow Studio - 8 Mi to Okemo Mtn!
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Living area
Sunny Stratton Townhome ~ 1 Mi to Skiing!
3.0 star property
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Efficient condo near slopes with kitchenette & great location
Efficient condo near slopes with kitchenette & great location
9.0 out of 10, Wonderful, (24)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
Efficient condo near slopes with kitchenette & great location
Don't see what you're looking for?
See all available properties in Chester
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Long Trail House at Stratton Mountain Resort
Living room
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (71)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (13)
"We liked the cottage and the tasteful renovations which preserved its historic nature. Loved the location's privacy and nature surrounding us. It was very warm over our stay and the AC units upstairs and down gave us more comfort. The linens were lovely, even if the mattress was a bit uncomfortable. There were no chairs on the deck and we wanted to sit outside often, so we bought inexpensive chairs and left them there. Our biggest complaint was with Vacasa's oversight. The cleaning crew did not...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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.

Frequently asked questions

What's it like to stay at an apartment in Chester?
You’ll find a lot of options for your stay in Chester with 67 accommodations. Though there aren’t many apartments, we can help you find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as vacation homes, condos, or cabins. During your trip, you can check out this relaxing area’s ski slopes and shops.
Are you thinking about apartments over traditional hotel rooms?
Often more spacious than a traditional hotel room, an apartment includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay in a quieter area.
What's a favorite apartment I should consider for a stay in Chester?
Here are some of the favorite apartments in the area: Hawks Mountain Farm, full apartment on a working farm.: Includes free WiFi, private patios, and sofa beds. Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly: Located 10.4 mi/16.7 km away in Ludlow. Private patios and sofa beds are included. Access to a spa tub is available on site. Efficient condo near slopes with kitchenette & great location: It’s situated in Ludlow, 10.9 mi/17.5 km away. Includes sofa beds.
What will the weather be like during my trip to Chester?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chester. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and April, with each month seeing an average of 15 inches of snowfall.
What should I see and do in Chester?
Chester is known for its ski slopes and shops. DaVallia Art & Accents and Bonnie’s Bundles Dolls are a couple of family-friendly sights. Vermont Country Store and Lowell Lake State Park are a couple of places you’ll find in the larger area.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the heart of the city. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.