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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester vacation rentals

Dining

1. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is CA $296
CA $605 total
includes taxes & fees
Nov 1 - Nov 2
Charming Chester Farmhouse near Near VT Slopes
Exterior

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is CA $396
CA $1,001 total
includes taxes & fees
Oct 20 - Oct 21
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A two-story house with a deck, surrounded by dense forest.

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is CA $762
CA $1,429 total
includes taxes & fees
Oct 21 - Oct 22
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A red house with a covered porch and a chimney.

4. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (173 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is CA $240
CA $526 total
includes taxes & fees
Oct 20 - Oct 21
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

5. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $73
CA $325 total
includes taxes & fees
Oct 20 - Oct 21
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

6. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is CA $79
CA $414 total
includes taxes & fees
Oct 25 - Oct 26
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A view of a grassy area with a ski lift and a building in the background.

7. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is CA $105
CA $377 total
includes taxes & fees
Oct 20 - Oct 21
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

8. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is CA $159
CA $251 total
includes taxes & fees
Nov 3 - Nov 4
Fat Sheep Farm & Cabins
A golf course with a winding path, trees, and a distant mountain range.

9. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is CA $141
CA $325 total
includes taxes & fees
Oct 20 - Oct 21
Efficient condo near slopes with kitchenette & great location
A two-story house with a porch, a staircase, and a front door.

10. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is CA $141
CA $333 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Studio Condo with Great Location, WiFi & Kitchenette
A two-story house with a porch, a staircase, and a front door.

11. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...
United States
William
The price is CA $148
CA $384 total
includes taxes & fees
Oct 20 - Oct 21
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

12. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is CA $197
CA $392 total
includes taxes & fees
Oct 20 - Oct 21
Cozy cabin in charming Londonderry
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

13. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is CA $281
CA $573 total
includes taxes & fees
Nov 11 - Nov 12
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A picnic table and a fire pit by a lake with a forest in the background.

14. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $263
CA $480 total
includes taxes & fees
Oct 20 - Oct 21
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A rustic cabin with a covered porch, a small shed, and outdoor seating.

15. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $127
CA $222 total
includes taxes & fees
Oct 25 - Oct 26
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

16. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is CA $105
CA $316 total
includes taxes & fees
Oct 22 - Oct 23
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

17. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is CA $141
CA $291 total
includes taxes & fees
Nov 3 - Nov 4
Bridgewater Living - Ben&Jerry Suite
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

18. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is CA $105
CA $367 total
includes taxes & fees
Oct 20 - Oct 21
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A modern living room with a fireplace, a television, and a ceiling fan.

19. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is CA $260
CA $722 total
includes taxes & fees
Oct 21 - Oct 22
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
A cozy living room with a fireplace, comfortable seating, and a television.

20. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is CA $256
CA $576 total
includes taxes & fees
Oct 20 - Oct 21
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
Adriana 2-night trip
Posted 1 hour ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $251 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near DaVallia Art & Accents, or you can select a more remote option if you want 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 coffeehouses and restaurants.

What are some of the best vacation rentals in Chester?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Chester is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Chester?

Choose from 31 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

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 a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.