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

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Our top choices for Chester hotels

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

1. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Russell
$218 nightly
$251 total
Oct 7 - Oct 8
Total with taxes and fees
Water's Edge Resort & Spa
A sign for Pier Blue Guesthouse with a logo and name.
A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.
A train traveling along a river with autumn foliage in the background.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

2. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
David
$91 nightly
$104 total
Sep 29 - Sep 30
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
A modern lobby with leather sofas, a wooden reception desk, and a large abstract painting.
An indoor swimming pool with metal ladders and a tiled edge.
A well-lit kitchen with wooden cabinets, a breakfast bar, and various breakfast items displayed.
A multi-story hotel with a glass entrance and a sign reading "HYATT PLACE".

3. Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area
Montville
United States
Kristen
$110 nightly
$127 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Place Uncasville - Casino Area
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with a deck extending over the water, featuring large windows and a dining area.

4. Sound View Greenport

Sound View Greenport
Greenport
United States
William B
$261 nightly
$299 total
Oct 14 - Oct 15
Total with taxes and fees
Sound View Greenport
A spacious lobby with a sofa, armchairs, and a coffee table. There is a fireplace and a wall-mounted artwork.
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.
A modern hotel lobby with a reception desk, a coffee station, and a store named "The Market" with various items on display.
A kitchen with wine bottles, glasses, and a chalkboard menu.

5. New Haven Hotel

New Haven Hotel
Downtown New Haven
United States
Alphonse
$133 nightly
$153 total
Sep 29 - Sep 30
Total with taxes and fees
New Haven Hotel
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
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.
A spacious room with a large bed, a staircase, and a door leading to another room.

6. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Laurie
$279 nightly
$321 total
Sep 23 - Sep 24
Total with taxes and fees
Copper Beech Inn
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and potted plants, with a high ceiling and large windows.
A restaurant with a sign reading "Gourmet Square Food Court" and a large tree sculpture in the center.
A modern building with reflective glass facades and a clear sky.
A casino interior with a large, illuminated gaming area and a distinctive ceiling structure.

7. Mohegan Sun

Mohegan Sun
Montville
United States
Derek
$205 nightly
$236 total
Oct 19 - Oct 20
Total with taxes and fees
Mohegan Sun
A hotel room with a large bed, a desk, a chair, a window with curtains, and a television.
A multi-story hotel with a symmetrical facade, a covered entrance, and an American flag.
A compact hotel room with a kitchenette, a bed with a green bedspread, a sofa, a bedside table, and a window with curtains.
A compact room with a kitchenette, a sofa, a small table, and a window with curtains.

8. Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area
Montville
United States
Rachel L
$81 nightly
$93 total
Sep 27 - Sep 28
Total with taxes and fees
Microtel Inn & Suites by Wyndham Uncasville Casino Area
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 hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.
A dining area with tables and chairs, a clock on the wall, and a counter with food items.

9. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Julia
$101 nightly
$116 total
Oct 13 - Oct 14
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
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 Fairfield Inn & Suites Marriott hotel with a covered entrance, multiple floors, and a parking lot.

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

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Montville
United States
Elizabeth
$134 nightly
$154 total
Sep 28 - Sep 29
Total with taxes and fees
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.
A light blue bus with "THE SHOALS" written on the front, parked in a driveway with a house and garden in the background.
A modern living room with a blue sofa, light blue armchairs, a dining table, and a kitchen in the background.
A modern hotel room with a bed, a sofa, a coffee table, and a view of the city.

11. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Jessica
$254 nightly
$286 total
Oct 1 - Oct 2
Total with taxes and fees
The Shoals Suites and Slips
A round outdoor fire pit with flames, surrounded by wicker furniture and a white cushion.
A purple door with a welcome sign, a white staircase with a patterned rug, and a view of a building through the window.
A house with a porch, a stone foundation, and a lawn.
A cozy room with floral-patterned furniture, a stone fireplace, and a view of trees through a window with a floral valance.

12. Westbrook Inn B&B

Westbrook Inn B&B
Westbrook Center
United States
Holly
$255 nightly
$283 total
Oct 11 - Oct 12
Total with taxes and fees
Westbrook Inn B&B
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 large, two-story house with a wrap-around porch, multiple windows, and a chimney.
A bedroom with a large bed, a nightstand, a dresser, and a robe rack.

13. The Captain Stannard

The Captain Stannard
Westbrook Center
United States
Deborah
$216 nightly
$239 total
Oct 22 - Oct 23
Total with taxes and fees
The Captain Stannard
A white building with a porch, columns, and a flag.
A large white house with a front porch, a fire pit in the center, and a staircase leading to the entrance.
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.

14. Old Lyme Inn

Old Lyme Inn
Old Lyme
United States
David
Old Lyme Inn
A restaurant with tables set for dining, large windows offering a city view, and a chandelier.
A spacious lobby with a grand chandelier, plush seating, a chess table, and a classic fireplace.
A spacious lobby with high ceilings, wooden paneling, and a chandelier. There are multiple seating areas with armchairs and sofas.
A spacious lobby with a central coffee table, two armchairs, and a dining area in the background.

15. Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
Downtown New Haven
United States
Ted
$167 nightly
$192 total
Oct 12 - Oct 13
Total with taxes and fees
Omni New Haven Hotel at Yale
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 hotel room with two beds, a desk, and a view of a cityscape.

16. The Capitol Hotel

The Capitol Hotel
Downtown Hartford
United States
Ana
$101 nightly
$116 total
Sep 27 - Sep 28
Total with taxes and fees
The Capitol Hotel
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 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.
A motel with a two-story structure, a covered parking area, and a landscaped front yard with various plants.

17. Liberty Inn

Liberty Inn
Old Saybrook
United States
Adam
$89 nightly
$102 total
Oct 5 - Oct 6
Total with taxes and fees
Liberty Inn
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A large building with multiple floors, surrounded by a residential area with houses and a body of water.
A wooden pier extending into a body of water with a cloudy sky above.

18. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Jolyn
$248 nightly
$284 total
Oct 15 - Oct 16
Total with taxes and fees
The Harbor Front Inn
A deck with outdoor seating, overlooking a body of water with a sunset view.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A restaurant with green booths, wooden chairs, and round tables.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

19. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Morris
The Pridwin Hotel
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.
A two-story Victorian-style house with a balcony, a porch, and a small tower.
An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.

20. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
United States
Charles
$355 nightly
$408 total
Oct 4 - Oct 5
Total with taxes and fees
Saybrook Point Resort & Marina
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Where to stay in and around Chester

Chester offers a charming escape with its beautiful country scenery and serene destinations. Explore the essence of Vermont in nearby towns like Central Bristol, where family-friendly atmospheres and romantic spots await. Enjoy the great outdoors and create lasting memories in Chester’s inviting surroundings.
A wooden gazebo with a tiled roof, surrounded by lush greenery and trees.
A sandy beach with a breakwater, calm sea, and a clear sky.
A calm lake with reflections of trees and a house.
A calm river flanked by leafless trees and dry grass, with a house in the background.
A calm lake with tall reeds in the foreground, a house surrounded by trees in the background, and a clear blue sky above.

Westbrook

Discover Westbrook, a welcoming destination perfectly suited for families and nature enthusiasts seeking a delightful getaway. With beautiful beaches like Westbrook Town Beach and the expansive Hammonasset Beach State Park, visitors can enjoy fun in the sun and scenic views. Additionally, the Essex Steam Train offers a charming journey through the area's rich history. Located about 9 miles by car from Chester, Westbrook is a smart choice for travelers looking to experience a blend of relaxation and adventure.

A coastal town with a lighthouse, houses, and a river.
A coastal town with a lighthouse, houses, and a river.
A sunset over a calm sea with a pier extending into the water.
A coastal town with a prominent white lighthouse, houses, and a calm body of water during sunset.
A sunset view from a boat deck with multiple sailboats anchored in the water.

Old Saybrook

Plan your stay in Old Saybrook, a top-rated choice for couples and families looking for a convenient mix of nature and romance. With attractions like the Essex Steam Train, the beautiful Westbrook Town Beach, and the Katharine Hepburn Cultural Arts Center, you'll find plenty to explore. Located about 10 miles by car from Chester, Old Saybrook serves as a fantastic home base for your adventures, making it a smart choice for your vacation.

A calm river with clear water, surrounded by lush green trees and a rocky shoreline.
A forest stream with a small waterfall surrounded by rocks and trees.
A waterfall cascading through a forest with autumn foliage.
A marina with boats docked, surrounded by autumn foliage and a cloudy sky.
Photo by Erick

Deep River

Families and nature enthusiasts will love Deep River, known for its charming scenery and outdoor activities. Visitors can enjoy the Essex Steam Train, explore the beautiful Hammonasset Beach State Park, and relax at Westbrook Town Beach. With its diverse recreational offerings, Deep River makes for a perfect weekend getaway, appealing to those seeking both adventure and romance. Located about 3 miles from Chester, it's an ideal base for your vacation, making hotel bookings here a smart choice.

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

Immerse yourself in Chester Center, where families and couples can easily access outdoor adventures and cultural experiences. This charming neighborhood offers delightful attractions like the Gillette Castle State Park and the Essex Steam Train, perfect for exploring scenic landscapes and local history. With a marina and beach nearby, there’s plenty to enjoy during the warmer months. Located around Chester, Chester Center is a smart choice for your vacation stay, combining convenience with a wealth of activities.

Deep River Center

Travelers visiting the area often choose Deep River Center as their ideal base, especially couples and families seeking a blend of nature and culture. This charming neighborhood offers access to delightful activities, including the Essex Steam Train and Gillette Castle State Park, perfect for exploring scenic landscapes. With a vibrant local park and recreational areas nearby, Deep River Center provides a relaxing escape. Located about 3 miles from Chester, it’s a smart choice for those looking to enjoy a memorable vacation experience.

Stay near popular attractions in and around Chester

Chester, Connecticut, offers a perfect getaway for outdoor lovers and romantics alike. Explore the scenic Connecticut River, hike through Cockaponsett State Forest, and discover charming Chester points of interest. This idyllic destination promises unforgettable adventures and serene moments in nature.
A large, ancient stone building with multiple windows and a central staircase.
Photo by Brandon Miller

Gillette Castle State Park

9.0/10 (9 reviews)
Experience the best of outdoor adventure at Gillette Castle State Park, where stunning scenery and unique architecture await. Located about 3 miles from Chester, this park offers a perfect blend of exploration and relaxation, making it an ideal base for your Connecticut getaway.
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A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
Often cited as a favorite among families and history buffs, the Essex Steam Train offers a unique journey through Connecticut's scenic landscapes. This railway museum showcases the rich culture of steam locomotion and provides an engaging experience for visitors. Located about 5 miles by car from Chester, it makes for a convenient day trip.
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A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.
Photo by Shannon Willitts

Hammonasset Beach State Park

8.8/10 (137 reviews)
Ideal for travelers interested in outdoor adventures, Hammonasset Beach State Park offers stunning scenery and a vibrant atmosphere. Located about 10 miles from Chester, this state park features beautiful beaches and nature trails, making it a perfect spot for relaxation and exploration during your visit. Staying nearby provides easy access to its scenic delights.
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A sunset over a lake with a dock and a boat.
Photo by Dawn Johnson

Machimoodus State Park

Considered a premier spot for outdoor adventurers, Machimoodus State Park offers stunning scenery and a wealth of activities. Located about 6 miles from Chester, this park invites visitors to explore its beautiful landscapes and enjoy a rejuvenating escape in nature, making it a convenient retreat for a memorable vacation.
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Plattwood Park

An essential stop for families seeking outdoor fun, Plattwood Park offers a tranquil escape with its eco-friendly atmosphere. Just about 3 miles from Chester, it's an inviting spot for picnics and nature walks, making it a convenient choice for a relaxing day outdoors.
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Westbrook Town Beach

8.8/10 (36 reviews)
For beach lovers seeking a relaxing getaway, Westbrook Town Beach offers a perfect escape. With its inviting beach vibes, this scenic spot is an ideal location to unwind by the water. Located about 9 miles by car from Chester, it's a convenient destination for a sun-soaked day trip.
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Essex Island Marina

8.0/10 (8 reviews)
Perfectly suited for outdoor adventurers, Essex Island Marina offers a vibrant beach atmosphere and a range of activities to enjoy. Located about 6 miles by car from Chester, this marina is an ideal spot to relax and soak in the natural beauty of Connecticut's shoreline. Staying nearby ensures easy access to this scenic escape.
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East Haddam Historical Society and Museum

A must-see for history buffs, the East Haddam Historical Society and Museum offers a deep dive into the region's rich past and vibrant culture. Located about 4 miles from Chester, this inviting destination provides an enriching experience, making it an ideal stop during your exploration of the area.
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Learn more about Chester

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

See all hotels in Chester
A calm river with boats, wooden docks, and buildings along the shore.

Top Chester Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Beautiful and clean room and property with a gorgeous marina view. Friendly and helpful staff. I thoroughly enjoyed my stay, and intend to return."
Joseph 1-night trip
Posted 1 hour ago
Saybrook Point Resort & Marina
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

8/10 Good
"The hotel was nice, little old with some wearing, but generally good. The shuttle bus from the hotel to the Mohegan Casino was very helpful."
Yasuhiro 3-night trip
Posted 2 hours ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

8/10 Good
"N"
Stephanie 1-night trip
Posted 2 hours ago
Motel 6 New Haven - Branford, CT
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Nice room,"
Russell 1-night trip
Posted 7 hours ago
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Beautiful property.The staff were very accommodating ,helpful and friendly.The only complaint to report was the lack of on site eating facilities .We arrived on a rainy Sunday and the outside venue for lunch was closed.The bar did not serve food until 3:30.The only option was the Sunday buffet which was priced at $59.00pp.Starbucks was limited to a grilled cheese or a ham egg sandwich.We were forced to leave the property to have lunch . The espresso martini was priced at &20.00 a tad high .Overall it was an enjoyable stay."
Mary 1-night trip
Posted 18 hours ago
Water's Edge Resort & Spa
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

8/10 Good
"Close to the casino and cheaper than staying on their property"
Carol 1-night trip
Posted 21 hours ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

10/10 Excellent
"The property was very clean. Very well kept"
Eugene T 4-night trip
Posted 1 day ago
Best Western Plus New England Inn & Suites
Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

8/10 Good
"It was quiet and clean"
Jeri 1-night trip
Posted 1 day ago
Regency Inn & Suites New London, Mystic
Mohegan Sun

Mohegan Sun

10/10 Excellent
"Very rude. Ni smiles. Made me feel sad."
Denise 1-night trip
Posted 1 day ago
Mohegan Sun

More cheap stays in Chester

Red Roof Inn Mystic - New London

Red Roof Inn Mystic - New London

707 Colman Street, Building A New London CT
$67 nightly
$77 total
Oct 1 - Oct 2
Total with taxes and fees
5.8/10 (1,002 reviews)
Red Roof Inn Mystic - New London
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
$71 nightly
$82 total
Sep 27 - Sep 28
Total with taxes and fees
7.4/10 Good! (1,016 reviews)
Motel 6 New Haven - Branford, CT
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

1954 Norwich New London Tpke Montville CT
$81 nightly
$93 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (2,062 reviews)
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
$91 nightly
$104 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
Pier Blue Inn Old Saybrook - Essex
Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

269 North Frontage Road New London CT
$108 nightly
$124 total
Sep 23 - Sep 24
Total with taxes and fees
6/10 (1,003 reviews)
Regency Inn & Suites New London, Mystic
Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell

76 Berlin Road Cromwell CT
$161 nightly
$185 total
Oct 4 - Oct 5
Total with taxes and fees
Springhill Suites by Marriott Hartford Cromwell

Hotels in Chester with star-rating

Find out more about Chester

Top reasons to visit Chester

  • Scenic Outdoor Adventures: Chester boasts beautiful landscapes, perfect for hiking and exploring nature along the Connecticut River.
  • Charming Local Attractions: Discover theaters, operas, and historic houses that reflect the town's rich culture.
  • Quaint Town Atmosphere: Stroll through friendly streets filled with unique shops and delightful eateries.
  • Cozy Accommodations: Enjoy a variety of lodging options, from charming bed and breakfasts to comfortable hotels.
  • Budget-Friendly Experiences: Chester offers affordable activities and hidden gems for memorable family vacations.

Find great hotels near Chester

Discover the charming accommodations in Chester, Connecticut, perfect for every traveler. Whether you prefer a cozy bed and breakfast or a well-equipped hotel, Chester offers a variety of options to suit your needs. Enjoy amenities that cater to business travelers, pet-friendly policies, and easy access to beach activities. Explore the best hotels in Chester and find the perfect place to unwind during your vacation.

  • Red Roof Inn Meriden: Located 17 miles from Chester, Red Roof Inn Meriden offers a budget-friendly lodging experience ideal for business travelers and pet owners. This hotel provides a welcoming atmosphere for your furry friends, allowing dogs and cats with specific weight restrictions. Guests can take advantage of essential amenities while enjoying a hassle-free stay. With its convenient location, the hotel is perfect for those looking to balance work and leisure during their visit.
  • Baymont by Wyndham Branford/New Haven: Just 16 miles from Chester, Baymont by Wyndham Branford/New Haven caters to families and adventure enthusiasts alike. This budget-friendly hotel offers an array of nearby outdoor experiences, such as hiking, biking, and ziplining, ensuring a thrilling stay for guests of all ages. The property also provides thoughtful amenities for children, including complimentary cribs. Pet-friendly options with specific policies make it a great choice for those traveling with pets.
  • Sleep Inn & Suites Niantic North: Situated 15 miles from Chester, Sleep Inn & Suites Niantic North boasts a commendable guest rating of 8.4 out of 10. This budget-friendly hotel is well-suited for families and business travelers, offering amenities designed for the little ones, such as free cribs and window guards for safety. The comfortable accommodations and friendly service create a welcoming environment, making it an excellent choice for a memorable stay in the area.

Where to stay near Chester

Chester, Connecticut, offers a delightful blend of outdoor adventures and charming scenery, perfect for a romantic getaway or family vacation. Stroll through its quaint town filled with friendly faces, or breathe in the fresh air while exploring scenic views along the Connecticut River. Nearby attractions provide a budget-friendly atmosphere, ensuring unforgettable experiences in this picturesque region. Don't miss the chance to enjoy local parks and hidden gems that make Chester a must-visit destination.

  • Westbrook: Located 8 miles from Chester, Westbrook is a charming coastal town known for its picturesque scenery and outdoor activities. Visitors flock here primarily during the summer months, drawn by its beautiful beaches and romantic atmosphere. Enjoy a day at the family beach, attend a lively music concert, or indulge in a round of golf at one of the local courses. Westbrook also offers a variety of resorts where you can unwind and soak in the stunning views. The blend of nature and recreation makes this destination a perfect spot for relaxation and adventure.
  • Old Saybrook: Nestled 9 miles from Chester, Old Saybrook is a delightful city that boasts a rich history and charming coastal vibes. This destination sees a peak in visitors from June to August, who come to enjoy its scenic landscapes and outdoor experiences. The area is home to beautiful beaches and a national state park, providing ample opportunities for hiking and exploration. Popular attractions include recreational areas and golf courses, making it an excellent choice for both relaxation and activity. Whether you're seeking a romantic getaway or a family outing, Old Saybrook has something for everyone.
  • Deep River: Just 3 miles from Chester, Deep River is a hidden gem that offers a serene escape with its lush landscapes and tranquil lakes. Visitor numbers peak in the spring and summer, making it an ideal time to explore its recreational areas and local theater. Deep River’s proximity to a national state park and beautiful beaches provides plenty of outdoor adventures for nature lovers. The charming small-town atmosphere coupled with romantic scenery makes it a perfect destination for a peaceful retreat.

Things to do in Chester

Chester, Connecticut, is perfect for a romantic outdoor getaway, offering scenic beauty and a variety of activities. Explore local attractions like theaters and operas, or enjoy recreational areas for fun-filled experiences. This charming town is ideal for weekend getaways, where you can discover its unique amenities and unwind amidst picturesque landscapes.

Shopping

In Chester, visit local shops like The Bee & Thistle Inn for unique gifts and the Chester Mercantile for charming souvenirs. If you're up for a drive, consider stopping by the Tanger Outlets in Westbrook, about 10 miles away, featuring a variety of brand-name stores at discounted prices.

Recreation

Explore the serene atmosphere at The Spa at the Saybrook Point Inn, where you can indulge in rejuvenating treatments and enjoy stunning waterfront views. For outdoor relaxation, visit the nearby Chester Creek Preserve for tranquil walks amidst nature, perfect for unwinding and connecting with the environment.

Adventure

Explore the scenic trails at the Cockaponset State Forest for hiking and wildlife spotting. Check out the Connecticut River for kayaking and paddleboarding, offering stunning views of the riverbanks. For a unique thrill, try zip-lining at Adventure Park for an exhilarating experience among the treetops.

Nightlife

In Chester, Connecticut, enjoy a cozy atmosphere at The River Tavern, where you can savor craft cocktails and local brews. For live music, check out the Chester Historical Society’s events, offering a charming backdrop for socializing and entertainment under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chester

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are March and December to January, where the prices are slightly lower. This is in comparison to May and July to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool lets you set your budget, choose your desired location, and more. You can sort the results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you can refine your search by hotel type—if you check the Eco-certified filter, you'll be shown sustainable and eco-friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal.

Find the best attractions near Chester

Chester, Connecticut, is perfect for a romantic getaway filled with outdoor adventures and scenic beauty. Visitors can explore a variety of attractions, including national parks, picturesque beaches, and historic houses. Whether you're seeking adventure or a peaceful retreat, Chester offers a delightful mix of experiences that cater to nature lovers and history enthusiasts alike.

  • Hammonasset Beach State Park: Located 10 miles from Chester, this stunning state park offers a blend of scenic beauty and outdoor adventure. Enjoy miles of sandy beaches, hiking trails, and picnic areas, perfect for a day of exploration or relaxation by the shore.
  • Westbrook Town Beach: Only 9 miles from Chester, this charming beach is ideal for sunbathing, swimming, and enjoying the soothing sounds of the waves. The friendly atmosphere and beautiful views make it a great spot for families and friends alike.
  • Goose Island: Situated 8 miles from Chester, this serene island offers a peaceful escape with outdoor activities like kayaking and beachcombing. Experience the natural beauty and tranquil vibes while soaking up the sun on its sandy shores.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageAverage
March38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May57.9°F (14.4°C)Light RainMostly SunnySlightly HighSlightly High
June66.4°F (19.1°C)Light RainMostly SunnyAverageAverage
July73.8°F (23.2°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnySlightly LowAverage
November45.5°F (7.5°C)Light RainMostly SunnySlightly LowAverage
December37.8°F (3.2°C)Light RainMostly SunnyAverageSlightly Low

The nearest major airports for your trip to Chester

When visiting Chester, Connecticut, you have several airport options. New York's JFK Airport is located 86 miles away, with nearby luxury hotels like Arlo Williamsburg and The William Vale, both 11 miles from the airport. LaGuardia Airport, 84 miles away, offers upscale accommodations such as The Plaza and The Pierre, just 5 miles from the terminal. Alternatively, Hartford's Bradley International Airport is only 38 miles from Chester, featuring convenient hotels like DoubleTree by Hilton, just 1 mile away. Each airport provides various transportation services to facilitate your travel to Chester, ensuring a smooth arrival for your vacation.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester is its charming village center, especially for visitors looking for a walkable, boutique experience.The village center is a compact and walkable area characterized by its well-preserved historic buildings, independent shops, and art galleries. Main Street and North Main Street are the primary thoroughfares, featuring local eateries, a playhouse, and artisan studios. It's located along the Pattaconk Brook, offering a picturesque New England setting.Couples often find the village center ideal for a romantic getaway. They can enjoy leisurely strolls, browse unique shops, and dine at local restaurants, many of which offer outdoor seating in pleasant settings. The relaxed pace and scenic surroundings make it superb for unwinding.Solo travelers looking for a peaceful and engaging experience will also appreciate the village center. It's easy to navigate on foot, and there are various small businesses to explore, from bookshops to craft stores.
When is the best time to go to Chester?
The best time to go to Chester, Connecticut, is during the late spring (May to early June) and fall (September to October) when the weather is most pleasant for outdoor activities and exploring.Late spring offers comfortable temperatures, typically ranging from the 60s to low 70s Fahrenheit, making it ideal for walking around town, visiting local shops, and enjoying the Connecticut River. The foliage is lush, and gardens are in bloom. This period is particularly good for couples looking for a scenic getaway, as they can enjoy river cruises or explore nearby state parks without the peak summer crowds.The fall season brings stunning New England foliage, with vibrant reds, oranges, and yellows throughout the area, usually peaking in mid-October. Temperatures are generally in the 50s and 60s Fahrenheit, superb for scenic drives, hiking, and visiting local farms and orchards. This is an excellent time for families to visit, as many local events and festivals celebrate the harvest season, and the cooler weather is comfortable for outdoor excursions.While summer (July and August) is also popular, with warmer temperatures in the 70s and 80s, it can be more crowded.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from $77 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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