Chester Hotels from €72 - Fully Refundable Options

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Pet friendly

Hot tub

Apartment

Pool

Spa

Condo

Apart hotel

Chalet

Cottage

Cabin

Waterpark

Family friendly

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chester hotels

Pet-friendly

Breakfast included

Hotel

Bed & breakfast

Reserve now, pay later

Iron/ironing board (on request), free WiFi, bed sheets

1. Fullerton Inn

Chester Depot

Kirsty

€130

includes taxes & fees

8 Sept - 9 Sept

2. Stone Hearth Inn and Eatery

Chester

Olena

€195

includes taxes & fees

7 Sept - 8 Sept

Sauna, aromatherapy, hot stone massages, deep-tissue massages

Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen

3. Pointe at Castle Hill Resort

Cavendish

David

€114

includes taxes & fees

28 Aug - 29 Aug

Exclusive Suite, Multiple Beds, Kitchenette, Mountain View

4. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

€87

includes taxes & fees

3 Sept - 4 Sept

Suite, 1 King Bed, Non Smoking, Jetted Tub

5. Best Western Springfield Hotel

Springfield

Gerry

€152

includes taxes & fees

3 Sept - 4 Sept

Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed

6. Bromley View Inn

Bondville

William

€72

includes taxes & fees

1 Sept - 2 Sept

7. The Inn at Weathersfield

Perkinsville

Rula

€207

includes taxes & fees

30 Aug - 31 Aug

Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave

8. Claremont Motor Lodge

Claremont

Sergio

€102

includes taxes & fees

30 Aug - 31 Aug

9. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

€140

includes taxes & fees

2 Sept - 3 Sept

10. Harvest Barn Inn

Bellows Falls

Michael

€162

includes taxes & fees

31 Aug - 1 Sept

11. Main and Mountain Bar & Motel

Ludlow

Kristina

€138

includes taxes & fees

2 Sept - 3 Sept

12. The Black Bear Lodge at Stratton Mountain Resort

Stratton

Roberta

€135

includes taxes & fees

1 Sept - 2 Sept

13. The Hartness House

Springfield

Dan

€167

includes taxes & fees

30 Aug - 31 Aug

Premium bedding, desk, blackout curtains, iron/ironing board

14. The Common Man Inn & Restaurant

Claremont

Denis

€125

includes taxes & fees

7 Sept - 8 Sept

15. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Charlene

€120

includes taxes & fees

17 Sept - 18 Sept

Desk, blackout curtains, iron/ironing board, free WiFi

Combined shower/bathtub, hair dryer, towels

16. Royal Inn Claremont

Claremont

Eva

€101

includes taxes & fees

30 Aug - 31 Aug

17. The Manchester View

Manchester Center

Edward

€93

includes taxes & fees

31 Aug - 1 Sept

Signature Suite, Kitchen, Mountain View | Living area

18. Brittany Motel

Manchester Center

Elizabeth

€81

includes taxes & fees

31 Aug - 1 Sept

19. Sleep Woodstock Motel

Woodstock

John

€79

includes taxes & fees

31 Aug - 1 Sept

20. Otherland Hotel

Newfane

Omar

€158

includes taxes & fees

30 Aug - 31 Aug

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Where to stay in Chester

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

Chester Depot

A forest with autumn foliage in various colors.

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

Bonnie's Bundles Dolls

7.6/10 (4 reviews)

This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.

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DaVallia Art & Accents

10.0/10 (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.

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

Top Chester Hotel Reviews

Kimpton Taconic Hotel by IHG

10/10 Excellent

"Rooms were clean and comfortable ,staff was pleasant. Love the Manchester such a beautiful town."

Hampton Inn and Suites Manchester

10/10 Excellent

"Would have liked a safe in my room. Rooms were large and clean."

Hampton Inn Brattleboro

8/10 Good

"Very clean. Good full breakfast."

Best Western Plus Keene Hotel

8/10 Good

"Clean room breakfast was good"

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It was good!"

The Shire Woodstock

8/10 Good

"It was a nice and cozy place to stay and experience Woodstock VT."

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"👍"

Colonial Motel

8/10 Good

"X"

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good

"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

€91

14 Sept - 15 Sept

includes taxes & fees

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

€111

6 Sept - 7 Sept

includes taxes & fees

8.6/10 Excellent! (849 reviews)

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

€113

10 Sept - 11 Sept

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

€114

30 Aug - 31 Aug

includes taxes & fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

€125

10 Sept - 11 Sept

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

€146

2 Sept - 3 Sept

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Chester?

Located 25.2 mi (40.5 km) from the heart of Chester, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Kimpton Taconic Hotel by IHG and Holiday Inn Club Vacations Mount Ascutney Resort by IHG. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Mountainside 5-BR Ski-In/Out Okemo Villa: This holiday home rental outside of Chester is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 1 hot tub. See all 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 family accommodation in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Also, attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for children of all ages. Find more child-friendly accommodations in Chester.

What's the best place to stay for a romantic holiday in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favourite guest house for couples, and features free WiFi and a garden. See all romantic hotels in Chester.

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

Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top dog-friendly option for your stay. Motel in the Meadow is another option for a stay with your pet. 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. Kimpton Taconic Hotel by IHG and Keene Elm City Hotel, an Ascend Collection Hotel 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 Lowell Lake State Park 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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Dorset Holiday Rentals

Chester Hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Pointe at Castle Hill Resort

4. The Upper Pass Lodge at Magic Mountain

5. Best Western Springfield Hotel

6. Bromley View Inn

7. The Inn at Weathersfield

8. Claremont Motor Lodge

9. Blue Gentian Lodge at Magic Mountain

10. Harvest Barn Inn

11. Main and Mountain Bar & Motel

12. The Black Bear Lodge at Stratton Mountain Resort

13. The Hartness House

14. The Common Man Inn & Restaurant

15. Sun Lodge near Manchester VT, Ascend Collection Hotel

16. Royal Inn Claremont

17. The Manchester View

18. Brittany Motel

19. Sleep Woodstock Motel

20. Otherland Hotel

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

Bonnie's Bundles Dolls

DaVallia Art & Accents

Learn more about Chester

Top Chester Hotel Reviews

Kimpton Taconic Hotel by IHG

Hampton Inn and Suites Manchester

Hampton Inn Brattleboro

Best Western Plus Keene Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

The Shire Woodstock

The Palmer House Resort, an Ascend Collection Hotel

Colonial Motel

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

Latchis Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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