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Hotels in Chester

October 2026
10
November 2026

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Oct 16 - Oct 18
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Oct 23 - Oct 25

Where to stay in Chester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chester on Hotels.com. These Chester hotels consistently deliver on quality, location and traveler experience. Last updated on October 10, 2026.
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A large, two-story house with a wrap-around porch and a conservatory.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

1. Copper Beech Inn

Copper Beech Inn
Ivoryton
CNY1,867
CNY2,147 total
includes taxes & fees
Oct 20 - Oct 21
Copper Beech Inn
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.
A spacious lobby with a fireplace, a round table with a vase of flowers, and a reception desk.
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

2. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
CNY1,194
CNY1,489 total
includes taxes & fees
Nov 1 - Nov 2
Water's Edge Resort & Spa
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A hotel lobby with a reception desk, seating area, and a snack bar.
A hotel with a sign reading 'Quality Inn by Choice Hotels,' featuring a modern design with a prominent archway entrance, a parking lot, and landscaped areas with shrubs and flowers.

3. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
CNY649
CNY746 total
includes taxes & fees
Nov 10 - Nov 11
Quality Inn Old Saybrook - Westbrook
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.
A cozy room with floral-patterned furniture, a stone fireplace, and a view of trees through a window with a floral valance.
A purple door with a welcome sign, a white staircase with a patterned rug, and a view of a building through the window.
A sandy beach with footprints and a wooden structure extending into the water.

4. Westbrook Inn B&B

Westbrook Inn B&B
Westbrook Center
CNY1,984
CNY2,202 total
includes taxes & fees
Nov 10 - Nov 11
Westbrook Inn B&B
A cabin with a dining table set for two, a bicycle, and a small porch area.
A bedroom with a wooden headboard, a bed with white linens, a bedside table with a tray of breakfast items, and a window overlooking greenery.
A wooden interior with a table, chair, and a hanging lantern.
A small, black cabin in a forest with a large window.

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
East Haddam
CNY904
CNY1,347 total
includes taxes & fees
Nov 10 - Nov 11
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior
Front of property
A bedroom with a bed, two rugs, a nightstand, a lamp, and a wall clock.
Gazebo

6. The Scranton Seahorse Inn

The Scranton Seahorse Inn
Madison Center
CNY1,887
CNY2,095 total
includes taxes & fees
Nov 2 - Nov 3
The Scranton Seahorse Inn
A large hotel with multiple balconies and a beach area with sun loungers and umbrellas.
A covered porch with a view of the ocean, a wicker chair, and a small table.
A coastal hotel with a pier, beach, and boats.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.

7. Madison Beach Hotel

Madison Beach Hotel
Madison Center
CNY1,656
CNY1,904 total
includes taxes & fees
Nov 10 - Nov 11
Madison Beach Hotel
A parking lot with a building in the background.
A motel with a large parking lot and multiple rooms.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

8. Clinton Motel

Clinton Motel
Clinton
CNY522
CNY600 total
includes taxes & fees
Oct 13 - Oct 14
Clinton Motel
A marina with boats docked, a fire pit table, and outdoor seating.
A two-story Victorian-style house with a balcony, a porch, and a small tower.
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
Dining

9. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
CNY1,870
CNY2,385 total
includes taxes & fees
Nov 3 - Nov 4
Saybrook Point Resort & Marina
A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.
A living room with a fireplace, a television mounted above it, and two armchairs.
A two-story white house with black shutters, a covered porch, and a red umbrella.
A teal bicycle with a wicker basket parked in front of a white building with green shutters.

10. The Homestead

The Homestead
Madison Center
CNY1,668
CNY1,852 total
includes taxes & fees
Oct 13 - Oct 14
The Homestead
A living room with a stone fireplace, grey sofas, and a coffee table.
A bedroom with a large bed, a nightstand, a dresser, and a robe rack.
A modern lobby with a round gold table, a large framed floral painting, and a wooden desk.
A large, two-story house with a wrap-around porch, multiple windows, and a chimney.

11. The Captain Stannard

The Captain Stannard
Westbrook Center
CNY1,566
CNY1,738 total
includes taxes & fees
Oct 14 - Oct 15
The Captain Stannard
A breakfast bar with various food items and a coffee machine.
A hotel with a 'spark by Hilton' sign, a parking lot, and a covered entrance.
A hotel room with a bed, a desk, a chair, a TV, and a door.
A reception area with a wooden counter, a large abstract painting, and a green rug.

12. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
CNY609
CNY700 total
includes taxes & fees
Nov 1 - Nov 2
Spark by Hilton Guilford
A sign for Pier Blue Guesthouse with a logo and name.
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.
A train traveling along a river with autumn foliage in the background.

13. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CNY588
CNY676 total
includes taxes & fees
Nov 4 - Nov 5
Pier Blue Inn Old Saybrook - Essex
A garden with a fountain, various shrubs, and flower beds.
A reception area with a wooden counter, a bulletin board with various notices, a potted plant, and a door leading to another room.
A motel with a two-story structure, a covered parking area, and a landscaped front yard with various plants.
A hotel room with a large bed, two bedside lamps, a wooden nightstand, a desk with a chair, and a view of the outdoors through a window.

14. Liberty Inn

Liberty Inn
Old Saybrook
CNY596
CNY686 total
includes taxes & fees
Nov 10 - Nov 11
Liberty Inn
An outdoor patio area with seating, a fire pit, and umbrellas.
A spacious dining area with high tables and chairs, a patterned carpet, and pendant lighting.
A hotel room with a bed, a desk with a computer, a microwave, a small fridge, a chair, and a large window with curtains.
A modern room with white leather sofas, a small round table, a stone fireplace, and large windows.

15. Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven
Wallingford
CNY837
CNY963 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield by Marriott Inn & Suites Wallingford New Haven
Room
Balcony
Front of property
A room with a leather sofa, a television mounted on the wall, and a window with a decorative frame.

16. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
Old Saybrook
CNY530
CNY627 total
includes taxes & fees
Oct 11 - Oct 12
Motel 6 Old Saybrook, CT
A hotel room with a bed, a sofa, a table, and a lamp.
A hotel room with a bed, a desk, a chair, a sofa, and a window with curtains.
A parking lot with cars, a Sleep Inn & Suites building, and a clear blue sky.
An electric vehicle charging station with a sign indicating 'Electric Vehicle Parking Only While Charging.'

17. Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
Niantic
CNY677
CNY779 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Inn & Suites Niantic North
A modern bar area with a wooden bar counter, multiple stools, and a variety of liquor bottles.
A modern hotel entrance with a sign reading "Courtyard by Marriott."
A modern hotel lobby with a fireplace, comfortable seating, and a large window offering a view.
A modern hotel lobby with a large flat-screen TV, comfortable seating, a Starbucks coffee station, and a patterned carpet.

18. Courtyard New Haven Wallingford

Courtyard New Haven Wallingford
Wallingford
CNY959
CNY1,103 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard New Haven Wallingford
A modern lobby with a wooden ceiling, a large sofa, a coffee table, and a seating area with armchairs.
A reception area with a wooden reception desk, a modern light fixture, and a wall-mounted sign.
A spacious hotel lobby with a long row of blue chairs, a sofa, a TV mounted on the wall, and a wooden ceiling.
A kitchenette with a refrigerator stocked with beverages, a microwave, and a coffee machine.

19. Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
Niantic
CNY760
CNY874 total
includes taxes & fees
Oct 27 - Oct 28
Best Western Niantic - New London/Mystic Area
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A modern living room with a flat-screen TV, a red armchair, a grey sofa, a wooden entertainment unit, and a large window with curtains.
A hotel corridor with round tables, large windows, and a modern console table.
A modern hotel lobby with a central bar area, refrigerated beverage dispensers, and a seating area with tables and chairs.

20. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
Wallingford
CNY901
CNY1,037 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Wallingford/Meriden
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Go beyond your typical stay in Chester

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Pet friendly
Pet friendly
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Pool
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Hot tub
Hot tub
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Apart­ment
Apart­ment
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Spa
Spa
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Cottage
Cottage

Top neighborhoods in Chester

A plate of food with three square pieces topped with greens and caviar.
Photo by Annette Babek
A cocktail in a martini glass on a bar counter.
Photo by Annette Babek

Chester Center

The Chester Center neighborhood has lots to see including Norma Terris Theater and Connecticut Valley Railroad State Park Trail.

Top landmarks in Chester

Norma Terris Theater

If you want to see a show while you're in town, try and grab some tickets at Norma Terris Theater in Chester Center. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy the show and want to see another, Goodspeed Opera House and Ivoryton Playhouse are both not far.
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Chester Creek Marina

Imagine strolling along Chester Creek Marina for some great waterfront pics. It's located 2.8 mi (4.5 km) from central Chester.
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Learn more about Chester

Chester is well-known for its attractions such as Connecticut River and Chester Creek Marina.

See all hotels in Chester
A historic waterfront estate with a large white building featuring a balcony and a flagpole.

Check out reviews of Chester hotels guests love

A living room with a stone fireplace, grey sofas, and a coffee table.
A bedroom with a large bed, a nightstand, a dresser, and a robe rack.
A modern lobby with a round gold table, a large framed floral painting, and a wooden desk.
A large, two-story house with a wrap-around porch, multiple windows, and a chimney.

The Captain Stannard

The Captain Stannard
Westbrook Center

10/10 Exceptional

United States
Julie
The Captain Stannard
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.
A cozy room with floral-patterned furniture, a stone fireplace, and a view of trees through a window with a floral valance.
A purple door with a welcome sign, a white staircase with a patterned rug, and a view of a building through the window.
A sandy beach with footprints and a wooden structure extending into the water.

Westbrook Inn B&B

Westbrook Inn B&B
Westbrook Center

10/10 Exceptional

United States
david
Westbrook Inn B&B
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A large, two-story house with a wrap-around porch and a conservatory.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

Copper Beech Inn

Copper Beech Inn
Ivoryton

10/10 Exceptional

United States
Peter
Copper Beech Inn
A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.
A living room with a fireplace, a television mounted above it, and two armchairs.
A two-story white house with black shutters, a covered porch, and a red umbrella.
A teal bicycle with a wicker basket parked in front of a white building with green shutters.

The Homestead

The Homestead
Madison Center

10/10 Exceptional

United States
Mitchell
The Homestead
A large hotel with multiple balconies and a beach area with sun loungers and umbrellas.
A covered porch with a view of the ocean, a wicker chair, and a small table.
A coastal hotel with a pier, beach, and boats.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.

Madison Beach Hotel

Madison Beach Hotel
Madison Center

10/10 Exceptional

United States
Donald
Madison Beach Hotel
A marina with boats docked, a fire pit table, and outdoor seating.
A two-story Victorian-style house with a balcony, a porch, and a small tower.
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
Dining

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center

10/10 Exceptional

United States
Robin
Saybrook Point Resort & Marina
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.
A spacious lobby with a fireplace, a round table with a vase of flowers, and a reception desk.
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center

10/10 Exceptional

United States
Edyta
Water's Edge Resort & Spa
A cabin with a dining table set for two, a bicycle, and a small porch area.
A bedroom with a wooden headboard, a bed with white linens, a bedside table with a tray of breakfast items, and a window overlooking greenery.
A wooden interior with a table, chair, and a hanging lantern.
A small, black cabin in a forest with a large window.

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
East Haddam

10/10 Exceptional

United States
Marcus
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior
Front of property
A bedroom with a bed, two rugs, a nightstand, a lamp, and a wall clock.
Gazebo

The Scranton Seahorse Inn

The Scranton Seahorse Inn
Madison Center

10/10 Exceptional

United States
Torrey
The Scranton Seahorse Inn
A parking lot with a building in the background.
A motel with a large parking lot and multiple rooms.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

Clinton Motel

Clinton Motel
Clinton

10/10 Exceptional

United States
Amy
Clinton Motel
A cozy dining area with a brick fireplace, wooden chairs, and tables set for a meal.
A spacious lobby with a fireplace, seating area, and a reception desk.
A brick building with a sign that reads "Inn at Middletown."
An indoor swimming pool with clear water, a metal ladder, and a tiled floor.

Inn at Middletown

Inn at Middletown
Washington Street Historic District

10/10 Exceptional

United States
Anonymous traveler
Inn at Middletown
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A hotel lobby with a reception desk, seating area, and a snack bar.
A hotel with a sign reading 'Quality Inn by Choice Hotels,' featuring a modern design with a prominent archway entrance, a parking lot, and landscaped areas with shrubs and flowers.

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook

10/10 Exceptional

United States
Terry
Quality Inn Old Saybrook - Westbrook
A patio area with outdoor seating, a gazebo, and flags.
A spacious dining area with multiple tables and chairs, large windows with a marina view, and a modern kitchen with white cabinetry.
A large, two-story house with a wrap-around porch and a brick chimney.
A living room with blue upholstered chairs, a white fireplace, and a view of a gazebo through a large window.

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
Niantic

10/10 Exceptional

United States
NianticQuaint
Inn at Harbor Hill Marina
A modern lobby with a wooden ceiling, a large sofa, a coffee table, and a seating area with armchairs.
A reception area with a wooden reception desk, a modern light fixture, and a wall-mounted sign.
A spacious hotel lobby with a long row of blue chairs, a sofa, a TV mounted on the wall, and a wooden ceiling.
A kitchenette with a refrigerator stocked with beverages, a microwave, and a coffee machine.

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
Niantic

10/10 Exceptional

United States
Al
Best Western Niantic - New London/Mystic Area
An outdoor kitchen with a grill and a built-in stove, white chairs, and a red door.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.
A multi-story hotel with a central entrance, a parking lot, and landscaped areas with shrubs and flowers.
A hotel lobby with a stone fireplace, multiple seating areas including a sofa and chairs, and a television mounted on the wall.

Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
Wallingford

10/10 Exceptional

United States
Anonymous traveler
Homewood Suites by Hilton Wallingford-Meriden
A modern bar area with a wooden bar counter, multiple stools, and a variety of liquor bottles.
A modern hotel entrance with a sign reading "Courtyard by Marriott."
A modern hotel lobby with a fireplace, comfortable seating, and a large window offering a view.
A modern hotel lobby with a large flat-screen TV, comfortable seating, a Starbucks coffee station, and a patterned carpet.

Courtyard New Haven Wallingford

Courtyard New Haven Wallingford
Wallingford

10/10 Exceptional

United States
Michelle
Courtyard New Haven Wallingford

Frequently Asked Questions

How much does a hotel room cost in Chester?

You can find top hotels in Chester from CNY449 with options to suit your budget and needs. If you're looking for an affordable hotel in Chester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Chester hotels?

Discover great deals on Chester hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. And make sure to check out our last-minute deals on Chester hotels.

Can I book Chester hotels with free cancellation?

It's easy to book a refundable Chester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

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