Chester Holiday Rentals, Vermont: Private House Rentals

Our top choices for Chester hotels

Fullerton Inn

Chester Depot

Rob

฿4,945 total

includes taxes & fees

29 May - 30 May

Stone Hearth Inn and Eatery

Chester

Olena

฿7,430 total

includes taxes & fees

9 Jun - 10 Jun

Signature Suite, Kitchen, Mountain View | Living area | 42-inch TV with cable channels

Brittany Motel

Manchester Center

Andrew

฿2,692 total

includes taxes & fees

2 Jun - 3 Jun

Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Woodstock

Elisabeth

฿4,477 total

includes taxes & fees

3 Jun - 4 Jun

Bromley View Inn

Bondville

Donna

฿3,055 total

includes taxes & fees

2 Jun - 3 Jun

Four Columns Inn

Newfane

Mark

฿4,642 total

includes taxes & fees

3 Jun - 4 Jun

Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, individually decorated

Claremont Motor Lodge

Claremont

Eric

฿3,895 total

includes taxes & fees

31 May - 1 Jun

The Burrell House

Keene

Charles

฿4,524 total

includes taxes & fees

2 Jun - 3 Jun

Chalet 239

West Dover

Patrick

฿4,814 total

includes taxes & fees

17 Jun - 18 Jun

The Jackson

West Woodstock

Courtney

฿5,654 total

includes taxes & fees

4 Jun - 5 Jun

Colonel Williams Inn

Brattleboro

Billie

฿5,654 total

includes taxes & fees

2 Jun - 3 Jun

The Inn at Weathersfield

Perkinsville

LUDJANE

฿7,505 total

includes taxes & fees

31 May - 1 Jun

Hampton Inn Brattleboro

Brattleboro

Savanna

฿4,547 total

includes taxes & fees

14 Jun - 15 Jun

Latchis Hotel

Brattleboro

Sharon

฿4,473 total

includes taxes & fees

2 Jun - 3 Jun

Stanford House

Manchester Center

Benjamin

฿4,411 total

includes taxes & fees

2 Jun - 3 Jun

Lincoln Inn & Gallery

West Woodstock

Elisabeth

฿6,785 total

includes taxes & fees

1 Jun - 2 Jun

The Putney Inn

Putney

Lori

฿3,376 total

includes taxes & fees

31 May - 1 Jun

Best Western Springfield Hotel

Springfield

Adina

฿6,107 total

includes taxes & fees

4 Jun - 5 Jun

Standard Room, 2 Double Beds | Desk, blackout curtains, iron/ironing board, free WiFi

Royal Inn Claremont

Claremont

Carolina

฿3,541 total

includes taxes & fees

29 May - 30 May

The Black Bear Lodge at Stratton Mountain Resort

Stratton

Paul

฿5,884 total

includes taxes & fees

31 May - 1 Jun

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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.

Chester Depot

panoramic view of colorful foliage in White mountain national forest in New Hampshire along Kancamagus highway

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

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Stay near popular Chester attractions

DaVallia Art & Accents

5.0/5 (2 reviews)

This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.

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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

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

On The River Inn

10/10 Excellent

"We had one of the apartments out back and it was really nice. The staff was very responsive and helpful. We had dinner at the restaurant and the food was very good and the waiter, Brian I think, was a very nice deadpan comedian. We enjoyed the hot tub too! The only thing we didn't appreciate was that it took about 10 minutes of running the water to get hot water for the sinks and showers. Not really a problem to wait, but it seems a waste of water."

Hampton Inn Brattleboro

8/10 Good

"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. It was really hard getting an early check in, much harder than one would expect given the occupancy. We did end up getting it in plenty of time, which we appreciated. (It seemed like there were challenges with staffing.) We enjoyed our stay and would stay there again."

The Covered Bridge Inn

4/10 Poor

"I don’t know where to begin. The place smelled like cigarette smoke. When I tried to check in I had to ring a bell and was to come back as the front desk staff seemed to all go out to lunch. After finally checking in, the tv didn’t work, the iron is broken and spilled water everywhere when I tried to iron my clothes. The bathroom showers had mold everywhere and I was genuinely afraid to step on the carpet, barefooted or touch anything in the room. I had to put my own bedsheets and pillowcases on the bed and pillows in order to sleep the other night. At night, there’s a door right outside my window that bangs every 45 minutes due to people going in and out to smoke. I was up all night. There were questionable people outside at all times, outside of the place was super dirty and trashy. Had i known this place was like that I wouldn’t have stayed. Needless to say I will not be returning turning and in fact if I could ask for my money back, I would."

Best Western Plus Keene Hotel

2/10 Terrible

"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR AGAIN I even left a day early because I refused to raid a shower there"

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

฿3,218

฿3,491 total

11 Jun - 12 Jun

includes taxes & fees

7/10 Good! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Chester?

Based on our traveller data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Other good choices for your stay in the area are Woodstock Inn & Resort and Pointe at Castle Hill Resort. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What's the best dog-friendly accommodation option in Chester?

Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.

What are some accommodation options with pools in Chester?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Pointe at Castle Hill Resort and Kimpton Taconic Hotel by IHG are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 62 hotels and other accommodation options to choose from. Find out more about Chester.

What should I do while I'm visiting Chester?

A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and The Nature Museum in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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Our top choices for Chester hotels

Fullerton Inn

Stone Hearth Inn and Eatery

Brittany Motel

Sleep Woodstock Motel

Bromley View Inn

Four Columns Inn

Claremont Motor Lodge

The Burrell House

Chalet 239

The Jackson

Colonel Williams Inn

The Inn at Weathersfield

Hampton Inn Brattleboro

Latchis Hotel

Stanford House

Lincoln Inn & Gallery

The Putney Inn

Best Western Springfield Hotel

Royal Inn Claremont

The Black Bear Lodge at Stratton Mountain Resort

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

DaVallia Art & Accents

Learn more about Chester

Top Chester Hotel Reviews

On The River Inn

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Frequently asked questions

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