Chester Hotel & Accommodation Deals 2026 from NZ$136 - Fully Refundable Options

A calm river with boats, wooden docks, and buildings along the shore.

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Our top choices for Chester hotels

A cabin with a dining table set for two, a bicycle, and a small porch area.

A wooden interior with a table, chair, and a hanging lantern.

A compact kitchen with wooden walls, a window with a view of greenery, a built-in dishwasher, and a sink.

A small, black cabin in a forest with a large window.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Stephanie

NZ$359

includes taxes & fees

2 Nov - 3 Nov

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

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

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

2. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Amy

NZ$199

includes taxes & fees

1 Nov - 2 Nov

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 spacious room with a large bed, a staircase, and a door leading to another room.

3. Copper Beech Inn

Ivoryton

Gregg

NZ$570

includes taxes & fees

15 Oct - 16 Oct

A parking lot with a building in the background.

A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

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.

4. Clinton Motel

Clinton

Selena

NZ$160

includes taxes & fees

28 Oct - 29 Oct

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

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

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

An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

5. Water's Edge Resort & Spa

Westbrook Center

Toni and Zak

NZ$353

includes taxes & fees

4 Oct - 5 Oct

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.

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

6. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

virginia

NZ$160

includes taxes & fees

5 Oct - 6 Oct

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 modern living room with a flat-screen TV, a small table, a yellow armchair, a rocking chair, and a mini-fridge stocked with snacks.

7. Spark by Hilton Guilford

Guilford

LAURETTA

NZ$187

includes taxes & fees

1 Nov - 2 Nov

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

A motel with a two-story structure, a covered parking area, and a landscaped front yard with various plants.

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

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.

8. Liberty Inn

Old Saybrook

Grace

NZ$164

includes taxes & fees

1 Nov - 2 Nov

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.

9. Westbrook Inn B&B

Westbrook Center

Diane

NZ$584

includes taxes & fees

8 Oct - 9 Oct

A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

A multi-story residential building with blue trim and large windows.

A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.

A hotel lobby with a reception desk, a flat-screen TV mounted above a fireplace, and comfortable seating areas.

10. Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Laurie

NZ$138

includes taxes & fees

25 Oct - 26 Oct

A sunset over a body of water with a boat and a tree silhouetted against the sky.

A white building with a sign that reads "Solano Inn".

A hotel lobby with a reception desk, a black sofa, and a glass coffee table.

A bedroom with a large bed, a desk with chairs, and a dining area.

11. Solano Inn

Portland

Douglas

NZ$186

includes taxes & fees

5 Oct - 6 Oct

A cozy dining area with a brick fireplace, wooden chairs, and tables set for a meal.

An indoor swimming pool with clear water, a metal ladder, and a tiled floor.

A grand spiral staircase with a chandelier, marble flooring, and blue armchairs in a spacious lobby area.

A spacious lobby with a fireplace, seating area, and a reception desk.

12. Inn at Middletown

Washington Street Historic District

Diego

NZ$311

includes taxes & fees

20 Oct - 21 Oct

A living room with a stone fireplace, grey sofas, and a coffee table.

A dining room with a wooden table, six chairs, and a large window with curtains.

A modern lobby with a round gold table, a large framed floral painting, and a wooden desk.

A bedroom with a large bed, a nightstand, a dresser, and a robe rack.

13. The Captain Stannard

Westbrook Center

Deborah

NZ$394

includes taxes & fees

11 Oct - 12 Oct

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

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

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

14. Saybrook Point Resort & Marina

Old Saybrook Center

Christa

NZ$656

includes taxes & fees

1 Nov - 2 Nov

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 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.

A living room with a fireplace, a television mounted above it, and two armchairs.

15. The Homestead

Madison Center

Sherry

NZ$465

includes taxes & fees

12 Oct - 13 Oct

A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.

A sign for Lamplighter Motel with a 'VACANCY' sign next to it.

A hotel room with a bed, a small table, a chair, a painting on the wall, and a window with a curtain.

16. Lamplighter Motel - Clinton, Connecticut

Clinton

Steven

NZ$141

includes taxes & fees

6 Oct - 7 Oct

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 spacious living area with a fireplace, a reception desk, and a large window.

A modern room with white leather sofas, a small round table, a stone fireplace, and large windows.

17. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

samuel

NZ$246

includes taxes & fees

12 Oct - 13 Oct

A multi-story hotel with balconies and a beach view.

A coastal hotel with a pier, beach, and boats.

A covered porch with a view of the ocean, a wicker chair, and a small table.

A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.

18. Madison Beach Hotel

Madison Center

Michael

NZ$583

includes taxes & fees

2 Nov - 3 Nov

A modern lobby with a wooden ceiling, a large sofa, a coffee table, and a seating area with armchairs.

A spacious hotel lobby with a long row of blue chairs, a sofa, a TV mounted on the wall, and a wooden ceiling.

A reception area with a wooden reception desk, a modern light fixture, and a wall-mounted sign.

A modern hotel room with a wooden bed, a desk, and a chair.

19. Best Western Niantic - New London/Mystic Area

Niantic

Steven

NZ$233

includes taxes & fees

27 Oct - 28 Oct

A hotel room with a bed, a sofa, a table, and a lamp.

A cafe with a counter, coffee machines, and a seating area with tables and chairs.

An electric vehicle charging station with a sign indicating 'Electric Vehicle Parking Only While Charging.'

A parking lot with cars, a Sleep Inn & Suites building, and a clear blue sky.

20. Sleep Inn & Suites Niantic North

Niantic

alexander

NZ$176

includes taxes & fees

25 Oct - 26 Oct

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Our guide on where to stay in Chester

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

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

If you're spending some time in Chester Center, Norma Terris Theater and Connecticut Valley Railroad State Park Trail are top sights worth seeing.

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Stay near popular Chester attractions

Norma Terris Theater

The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes.

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Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewellery and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

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Top Chester Hotel Reviews

Recent Reviews in Chester

Mohegan Sun

10/10 Excellent

"Everything was fantastic, and the casino is huge. You are lacking for nothing when you stay at this hotel."

Motel 6 New Haven - Branford, CT

10/10 Excellent

"No es un lugar Waoo, pero si tienes mascotas y llevas tu detergentes para limpiar está bien, yo acostumbro a llevar mis sábanas propias para no quejarme, aunque no tengo ninguna queja que dar."

Inn at Middletown

10/10 Excellent

"Met my expectations and breakfast was wonderful!"

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Nice place !"

Best Western Plus New England Inn & Suites

10/10 Excellent

"Manager Mar"

Water's Edge Resort & Spa

10/10 Excellent

"They upgraded us to a balcony and there was a lot to do there. The pool and hot tub were nice too!"

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Great experience and the perfect environment"

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent

"Clean, served its purpose on a quick trip. Would stay here again on my next visit."

Red Roof Inn Meriden

10/10 Excellent

"The rooms was cozy, clean and quite"