Chester Cottages ￥25,674

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Our top choices for Chester cottages

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

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

Cavendish

Mark G.

￥79,164 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with two chairs and a small table, overlooking a green landscape.

2. Game Room, Fire Pit & Views! Spacious Ludlow Home

Ludlow

￥127,460 total

includes taxes & fees

Nov 10 - Nov 11

3. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Stratton

￥114,370 total

includes taxes & fees

Nov 10 - Nov 11

A green wooden house with a sloped roof and a front porch.

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Ludlow

￥340,824 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester

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

Top reviews in Chester

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 two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

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 two-story white house with a porch, a front yard, and a mailbox.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A brick building with a covered patio area, a large tree, and a sign indicating no parking.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

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 red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

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 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 calm lake reflecting a forest with autumn foliage.

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 white two-story house with a front porch, a covered patio, and a well-maintained garden.

The Weston

Weston

10/10 Excellent

astrid

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

A two-story wooden building with a garage, a covered outdoor area, and a car parked in front.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A two-story building with a porch, American flag, and two white rocking chairs.

The Reluctant Panther Inn and Restaurant

Manchester Village Historic District

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

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What is there to do in Chester near my cottage?

Once you've unpacked your suitcases, venture out and discover the incredible things Chester has on offer. DaVallia Art & Accents is a top attraction to add to your must-do list.

Search Chester Cottage Rentals

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Chester cottages

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

2. Game Room, Fire Pit & Views! Spacious Ludlow Home

3. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Learn more about Chester

Top reviews in Chester

Stone Hearth Inn and Eatery

10/10 Excellent

Frequently Asked Questions

Why book your cottage in Chester with Expedia?

How can I find cheap cottages in Chester?

What is there to do in Chester near my cottage?