Chester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Chester

Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$181 nightly
The price is $203
Dec 7 - Dec 8
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$295 nightly
The price is $330
Dec 7 - Dec 8
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo

Chester
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
$890 nightly
The price is $997
Dec 5 - Dec 6
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!

2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Dec 9 - Dec 10
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking

3.0 star property
Ludlow
$333 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ludlow Ski Cabin 2 Mi to Ski Parking
Exterior
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
$171 nightly
The price is $187
Dec 10 - Dec 11
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$317 nightly
The price is $346
Dec 8 - Dec 9
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior
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, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$327 nightly
The price is $366
Dec 15 - Dec 16
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
$488 nightly
The price is $546
Dec 7 - Dec 8
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (57)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$236 nightly
The price is $265
Dec 9 - Dec 10
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry

2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
$320 nightly
The price is $361
Dec 8 - Dec 9
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$289 nightly
The price is $327
Dec 21 - Dec 22
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Cozy Bromley Retreat

Bromley Mountain
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
$288 nightly
The price is $325
Dec 7 - Dec 8
Total with taxes and fees
Cozy Bromley Retreat
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Dec 7 - Dec 8
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
$309 nightly
The price is $335
Dec 14 - Dec 15
Total with taxes and fees
Owl's Nest Treehouse
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$386 nightly
The price is $436
Dec 7 - Dec 8
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Iron/ironing board, WiFi, bed sheets
Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Woodstock Suite | 10 Min to Mountains |A/C| Hiking

Bridgewater
10.0 out of 10, Exceptional, (5)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
$215 nightly
The price is $235
Dec 8 - Dec 9
Total with taxes and fees
Woodstock Suite | 10 Min to Mountains |A/C| Hiking
Fridge, microwave, oven, stovetop
Lake Front Family Friendly Escape

Lake Front Family Friendly Escape

Newport
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
$343 nightly
The price is $372
Dec 8 - Dec 9
Total with taxes and fees
Lake Front Family Friendly Escape
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$249 nightly
The price is $282
Dec 7 - Dec 8
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole
10.0 out of 10, Exceptional, (50)
"Worked out perfectly for us!"
United States
Andrew P.
$510 nightly
The price is $553
Dec 9 - Dec 10
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Wonderful place to stay!"
Robin 1-night trip
Posted 1 day ago
The Shire Woodstock

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $260 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home rental near Chester is located on the waterfront and has a balcony, a garden, 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. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals will I find in Chester?

Choose from 34 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. Stratton Mountain Resort and Grafton Historical Society 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.