Hotels in Chester

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Where to stay in Chester?

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 formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

A spacious lobby with a fireplace, a round table with a vase of flowers, and a reception desk.

1. Water's Edge Resort & Spa

Westbrook Center

$209

$258 total

includes taxes & fees

Nov 1 - Nov 2

A modern lobby with leather sofas, a wooden reception desk, and a large abstract painting.

A multi-story hotel with a glass entrance and a sign reading "HYATT PLACE".

An indoor swimming pool with metal ladders and a tiled edge.

A hotel room with a large bed, two bedside tables, a nightstand, a window with a view of greenery, and wall-mounted lights.

2. Hyatt Place Uncasville - Casino Area

Montville

$109

$125 total

includes taxes & fees

Nov 10 - Nov 11

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

3. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$84

$97 total

includes taxes & fees

Nov 5 - Nov 6

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach bar with wooden chairs and a small table, overlooking the sea.

A coastal building with large windows, a deck, and a view of the sea at sunset.

A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

4. Sound View Greenport

Greenport

$192

$248 total

includes taxes & fees

Nov 2 - Nov 3

A hotel room with a large bed, a desk, a chair, a window with curtains, and a television.

A compact room with a kitchenette, a sofa, a small table, and a window with curtains.

A compact hotel room with a kitchenette, a bed with a green bedspread, a sofa, a bedside table, and a window with curtains.

A multi-story hotel with a symmetrical facade, a covered entrance, and an American flag.

5. Microtel Inn & Suites by Wyndham Uncasville Casino Area

Montville

$77

$89 total

includes taxes & fees

Oct 26 - Oct 27

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 hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

A bar area with a long counter, multiple stools, and a well-stocked bar.

6. Copper Beech Inn

Ivoryton

$279

$321 total

includes taxes & fees

Oct 12 - Oct 13

A spacious lobby with a sofa, armchairs, and a coffee table. There is a fireplace and a wall-mounted artwork.

A modern kitchen with stainless steel appliances, wooden cabinets, and a wine display.

A modern hotel lobby with a reception desk, a coffee station, and a store named "The Market" with various items on display.

A modern living room with a blue sofa, white ottoman, and a grey armchair. There are two lamps on side tables, and a framed artwork on the wall.

7. New Haven Hotel

Downtown New Haven

$135

$155 total

includes taxes & fees

Oct 27 - Oct 28

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

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.

8. Quality Inn Old Saybrook - Westbrook

Old Saybrook

$97

$111 total

includes taxes & fees

Nov 1 - Nov 2

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.

9. The Captain Stannard

Westbrook Center

$234

$260 total

includes taxes & fees

Oct 12 - Oct 13

A corner market with a refrigerated beverage display, snack shelves, and a sign reading "The Corner Market".

A hotel room with a bed, a sofa, a desk with a chair, a TV, and a small table.

A modern reception area with a wooden reception desk, a large blue decorative wall, and a colorful rug.

A buffet counter with various food items and kitchen appliances.

10. Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Montville

$125

$144 total

includes taxes & fees

Nov 2 - Nov 3

A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.

A house with a porch, a stone foundation, and a lawn.

A purple door with a welcome sign, a white staircase with a patterned rug, and a view of a building through the window.

A cozy room with floral-patterned furniture, a stone fireplace, and a view of trees through a window with a floral valance.

11. Westbrook Inn B&B

Westbrook Center

$296

$329 total

includes taxes & fees

Oct 12 - Oct 13

A white building with a porch, columns, and a flag.

A spacious living room with a piano, a sofa, and a coffee table. There is a door leading to another room and a window with a view.

A table set for dining with candles, glasses, and floral centerpieces.

A large white house with a front porch, a fire pit in the center, and a staircase leading to the entrance.

12. Old Lyme Inn

Old Lyme

A garden with a fountain, various shrubs, and flower beds.

A kitchen with wooden cabinets, a refrigerator, a coffee maker, and a fruit bowl.

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.

13. Liberty Inn

Old Saybrook

$89

$102 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with a large bed, two bedside lamps, a desk with a chair, a large window with curtains, and an air conditioning unit.

A vending machine with a glass front, a refrigerated display case, and a snack shelf.

A bathroom with a pedestal sink, a bathtub, a shower curtain, and a mirror with a towel rack.

A beverage cooler with various drinks and a snack wall with assorted snacks and beverages.

14. The Capitol Hotel

Downtown Hartford

$109

$125 total

includes taxes & fees

Nov 1 - Nov 2

A living room with a piano, a sofa, a plaid armchair, and a fireplace.

A historic building with a mural, a well-maintained lawn, and vibrant pink flowers.

A room with a wooden staircase, green walls, and a wall covered with framed photographs.

A room with a wooden bench, a table with a lamp, a mirror, and a fireplace.

15. Higganum House B&B

Higganum

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.

A storefront with a sign reading "THE SHOALS".

16. The Shoals Suites and Slips

Southold

$269

$332 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with tables and chairs, large windows with curtains, and a view of a cityscape.

A hotel room with two sofas, a coffee table, and a chair. There are large windows with curtains and a view of the city.

A spacious lobby with a central seating area, a chandelier, and wooden paneling.

A hotel room with a large bed, a television, a desk, and a view of the city.

17. Omni New Haven Hotel at Yale

Downtown New Haven

$161

$185 total

includes taxes & fees

Oct 11 - Oct 12

A parking lot with a building in the background.

A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

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.

18. Clinton Motel

Clinton

$78

$90 total

includes taxes & fees

Oct 13 - Oct 14

A marina with boats docked, a fire pit table, and outdoor seating.

An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.

An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.

A two-story Victorian-style house with a balcony, a porch, and a small tower.

19. Saybrook Point Resort & Marina

Old Saybrook Center

$279

$356 total

includes taxes & fees

Nov 3 - Nov 4

A two-story house with a balcony, outdoor seating area, and a variety of plants.

A restaurant with a signboard listing its hours of operation.

A bar area with stools, a shelf with glasses, and decorative plants.

A bathroom with a bathtub, green tiled walls, and windows with white blinds.

20. Zey Hotel

Greenport

$203

$231 total

includes taxes & fees

Oct 12 - Oct 13

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Go beyond your typical stay in Chester

Pet friendly

Pool

Spa

Hot tub

Family friendly

Top neighborhoods in Chester

Chester Center

A plate of food with three square pieces topped with greens and caviar.

A cocktail in a martini glass on a bar counter.

Chester Center

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

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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

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent

"Nice place to stay."

Mohegan Sun

10/10 Excellent

"Wonderful overnight stay!!"

Best Western Plus New England Inn & Suites

8/10 Good

"The lady who does breakfast is exceptional. Friendly and keeps her station spotless and loaded up with items. The hotel should be very proud to have her. I didn't see her name, but having stayed at this hotel a few times she is the regular lady here."

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Great experience. Nice clean and quiet."

Hilton Garden Inn Wallingford/Meriden

10/10 Excellent

"We were there for only 1 night for a concert, but the grounds, public areas and rooms were clean, comfortable and relaxing. The staff was friendly, kind and helpful. Would stay again and I would recommand you to friends and relatives. Food wise was okay, but pricey."

Clarion Inn North Haven - New Haven North

10/10 Excellent

"Room and bedding super clean. Staff very friendly and helpful. Property was messy because of construction. Not great for walking your dog."

Frequently asked questions

What hotels do travelers like in Chester?

Guests like Pier Blue Inn Old Saybrook - Essex, Water's Edge Resort & Spa and Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy.

Can I book refundable accommodations in Chester?

If you need the flexibility to change your plans to Chester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

What will the weather in Chester be like during my vacation?

July and August are typically the warmest months in Chester when the average temp is 70°F. January and February are the coldest months when the average temperature is 35°F. October and December are the months with the most rain.

Why should I book my Chester accommodation with Hotels.com?

There are plenty of reasons to book your Chester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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