A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Chester Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

In two weeks

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In three months

In four months

Our top choices for Chester vacation rentals

1. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

$328 nightly

Nov 9 - Nov 10

Total with taxes and fees

A two-story house with a deck, surrounded by dense forest.

2. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

$831 nightly

Nov 9 - Nov 10

Total with taxes and fees

A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

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

Andover

Lorraine C.

$582 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

4. Cozy Village Condo-Okemo Shuttle

Ludlow

Vanessa W.

$221 nightly

Nov 9 - Nov 10

Total with taxes and fees

A red house with a covered porch and a chimney.

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

Grafton

Kathy H.

$323 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

6. Fat Sheep Farm & Cabins

Windsor

Brenda

$168 nightly

Nov 22 - Nov 23

Total with taxes and fees

A view of a grassy area with a ski lift and a building in the background.

7. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Clock Tower Base Area

Danna K.

$233 nightly

Nov 10 - Nov 11

Total with taxes and fees

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

8. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

$202 nightly

Nov 11 - Nov 12

Total with taxes and fees

A golf course with a winding path, trees, and a hilly landscape.

9. First-floor downtown studio near dining and gear shops, under a mile to Okemo

Ludlow

Brian

$270 nightly

Nov 11 - Nov 12

Total with taxes and fees

A golf course with a winding path, trees, and a distant mountain range.

10. Compact downtown studio condo with kitchenette near the Okemo slopes

Ludlow

Frank R.

$208 nightly

Nov 11 - Nov 12

Total with taxes and fees

A two-story house with a porch, a staircase, and a front door.

11. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Ludlow

Zach S.

$242 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

12. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Londonderry

Michael D.

$300 nightly

Nov 9 - Nov 10

Total with taxes and fees

13. Downtown studio with kitchenette, shuttle stop right across the street

Ludlow

Mikhail R.

$214 nightly

Nov 11 - Nov 12

Total with taxes and fees

A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

14. Long Trail House 368 condo in Stratton Village, walk to the lifts

Stratton

$225 nightly

Nov 9 - Nov 10

Total with taxes and fees

A wooden cabin interior with a staircase, a sofa, and a table.

15. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

$367 nightly

Nov 11 - Nov 12

Total with taxes and fees

A building with a sign reading 'Fire Tower Restaurant & Tavern.'

16. Fourth-floor Stratton Village studio with valley-view balcony

Stratton

$199 nightly

Nov 9 - Nov 10

Total with taxes and fees

A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

17. Village Fireplace Shuttle Boot Warmers

Ludlow

Justin P.

$375 nightly

Nov 30 - Dec 1

Total with taxes and fees

A covered porch with wicker furniture, a table, and chairs.

18. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

$433 nightly

Nov 9 - Nov 10

Total with taxes and fees

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

19. Cozy cabin in charming Londonderry

Londonderry

Eric H.

$225 nightly

Nov 9 - Nov 10

Total with taxes and fees

A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

20. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton

eric m.

$275 nightly

Nov 9 - Nov 10

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Chester Hotel Reviews

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

Fullerton Inn

Chester Depot

10/10 Excellent

Catherine

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

JULIA

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

Pointe at Castle Hill Resort

Cavendish

10/10 Excellent

This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...

Marion

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A large two-story house with a front porch and a well-maintained lawn.

The Landgrove

Londonderry

10/10 Excellent

The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the...

Rita

A large, snow-covered house with multiple windows and a well-lit porch.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

A restaurant with tables set for dining, chairs, and a fireplace in the background.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Anonymous traveler

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

A large stone building with a steep roof, surrounded by dense forest and hills.

Castle Hill Resort And Spa

Cavendish

10/10 Excellent

STAFF I want to start by pointing out that the staff at the hotel were above and beyond PHENOMENAL, and I mean ALL THE STAFF. I spent the weekend up there and got stuck with some car problems in a blizzard and dealt with everybody on the staff there. They were some of the nicest people I have ever dealt with in the hospitality industry. When I say all the staff, I mean all the staff! DAY 1. The plow guy helped me get my car out of a spot when my snow chain broke and I couldn’t move. DAY 2...

Steven

A hotel with a covered entrance, a clear sky, and a tree in the foreground.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Excellent

Anthony

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

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 $183 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.

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.

Chester Vacation Rentals

Check prices for these dates

Our top choices for Chester vacation rentals

1. Charming Chester Farmhouse near Near VT Slopes

2. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

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

4. Cozy Village Condo-Okemo Shuttle

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

6. Fat Sheep Farm & Cabins

7. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

8. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

9. First-floor downtown studio near dining and gear shops, under a mile to Okemo

10. Compact downtown studio condo with kitchenette near the Okemo slopes

11. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

12. Beautiful country cabin with hot tub and outdoor shower in Londonderry

13. Downtown studio with kitchenette, shuttle stop right across the street

14. Long Trail House 368 condo in Stratton Village, walk to the lifts

15. Adventure Cabin Hot Tub Sauna Trails Game Area

16. Fourth-floor Stratton Village studio with valley-view balcony

17. Village Fireplace Shuttle Boot Warmers

18. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

19. Cozy cabin in charming Londonderry

20. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Stone Hearth Inn and Eatery

10/10 Excellent

Find out more about Chester

Everything you need to know about Chester vacation rentals

Chester vacation rentals: An excellent choice for every season

How to find incredible deals on Chester rentals

Frequently Asked Questions

Are there vacation rentals in Chester?

What are some of the best vacation rentals in Chester?

How many vacation rentals will I find in Chester?

What’s there to see and do in Chester?

What’s a vacation rental in Chester like?

Explore a world of travel with Expedia