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

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18 Aug - 19 Aug
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19 Aug - 20 Aug
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21 Aug - 23 Aug
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28 Aug - 30 Aug

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Our top choices for Chester hotels

Bed & breakfast
Hotel
Breakfast included
Pet-friendly
Motel

1. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
John
NZ$197
includes taxes & fees
13 Sept - 14 Sept
Quality Inn Old Saybrook - Westbrook

2. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
East Haddam
United States
Frank
NZ$419
includes taxes & fees
17 Sept - 18 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

3. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NZ$544
includes taxes & fees
19 Aug - 20 Aug
Copper Beech Inn

4. Clinton Motel

Clinton Motel
Clinton
United States
John
NZ$154
includes taxes & fees
2 Sept - 3 Sept
Clinton Motel

5. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
United States
Stacy
NZ$206
includes taxes & fees
30 Aug - 31 Aug
Spark by Hilton Guilford

6. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Egor
NZ$187
includes taxes & fees
10 Sept - 11 Sept
Pier Blue Inn Old Saybrook - Essex

7. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
NZ$154
includes taxes & fees
19 Aug - 20 Aug
Lamplighter Motel - Clinton, Connecticut

8. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
Old Saybrook
United States
Kenneth
NZ$157
includes taxes & fees
25 Aug - 26 Aug
Econo Lodge Inn & Suites Old Saybrook Westbrook

9. Liberty Inn

Liberty Inn
Old Saybrook
United States
William
NZ$174
includes taxes & fees
24 Aug - 25 Aug
Liberty Inn

10. Solano Inn

Solano Inn
Portland
United States
Douglas
NZ$159
includes taxes & fees
19 Aug - 20 Aug
Solano Inn

11. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Thomas
NZ$483
includes taxes & fees
16 Sept - 17 Sept
Water's Edge Resort & Spa

12. Westbrook Inn B&B

Westbrook Inn B&B
Westbrook Center
United States
Diane
NZ$577
includes taxes & fees
30 Aug - 31 Aug
Westbrook Inn B&B

13. The Captain Stannard

The Captain Stannard
Westbrook Center
United Kingdom
Jessica
NZ$420
includes taxes & fees
17 Sept - 18 Sept
The Captain Stannard

14. Tower Inn And Suites Of Guilford - Madison

Tower Inn And Suites Of Guilford - Madison
Guilford
United States
Christina
NZ$214
includes taxes & fees
19 Aug - 20 Aug
Tower Inn And Suites Of Guilford - Madison

15. Baymont by Wyndham Branford/New Haven

Baymont by Wyndham Branford/New Haven
Branford
United States
jennifer
NZ$193
includes taxes & fees
19 Aug - 20 Aug
Baymont by Wyndham Branford/New Haven

16. Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
Niantic
United States
Berney
NZ$182
includes taxes & fees
8 Sept - 9 Sept
Sleep Inn & Suites Niantic North

17. Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven
Wallingford
United States
Thierry
NZ$244
includes taxes & fees
6 Sept - 7 Sept
Fairfield by Marriott Inn & Suites Wallingford New Haven

18. Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London
Niantic
United States
John
NZ$175
includes taxes & fees
19 Aug - 20 Aug
Motel 6 Niantic, CT - New London

19. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
United States
Charles
NZ$742
includes taxes & fees
3 Sept - 4 Sept
Saybrook Point Resort & Marina

20. Inn at Middletown

Inn at Middletown
Washington Street Historic District
United States
Dale
NZ$351
includes taxes & fees
8 Sept - 9 Sept
Inn at Middletown
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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

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

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.
See properties

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.

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

Top Chester Hotel Reviews

Recent Reviews in Chester

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

8/10 Good
"Hotel worked well for a quick place to sleep on a long roadtrip with my dog. Lots of options for quick takeout dinner (no microwave was ok) and shower was adequate (no shampoo) but price was right and they did not charge extra for a dog. Quiet on a Monday night made sleeping easy. Bare bones room. Just so you know not to expect much in way of amenities."
Tracey 1-night trip
Posted 1 hour ago
Motel 6 New Haven - Branford, CT
Hampton Inn Norwich

Hampton Inn Norwich

8/10 Good
"Staff was friendly, breakfast was delicious. There were several options, eggs, bacon, sausage, waffles cereal, bagels, etc. Water was $4.50 for. Small bottle, but you could refill your bottles in the gym. We did not use the gym or pool."
Stacy 2-night trip
Posted 2 hours ago
Hampton Inn Norwich
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent
"Clean, nice staff, breakfast good, great overall"
Jean 1-night trip
Posted 3 hours ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Red Roof Inn Meriden

Red Roof Inn Meriden

8/10 Good
"Clean and pet-friendly, quiet"
Lynn 1-night trip
Posted 23 hours ago
Red Roof Inn Meriden
Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

8/10 Good
"Good size room. Bathroom needs help Shower leaks,almost missed the tiny soap more towels needed if staying more than one day Overall it was ok"
Janet and Walter 2-night trip
Posted 1 day ago
Regency Inn & Suites New London, Mystic
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

8/10 Good
"We have stayed here several times over the last couple of years. The staff is always nice and friendly. The free hot breakfast has a nice selection of foods. The area is nice and safe. Parking our truck and trailer was a little tight. Nice rooms and comfortable mattresses. I would recommend staying at this hotel."
Michael 3-night trip
Posted 1 day ago
Best Western Plus New England Inn & Suites
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

8/10 Good
"Our second time at post card cabins and we really enjoy it. Our only complaint this time around is that we texted saying we didn’t need anything replenished and then someone showed up midday and loudly knocked on our cabin (after we had just fallen asleep for a nap) so that was unfortunate. Also the people working there should have a logo or something on them because I was startled when I opened the door and had no clue who the person was initially. It would also be nice if you could request a certain cabin, not sure if this is something they allow but will look into it for future visits as some have much better parking options than others."
Francesca 2-night trip
Posted 1 day ago
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent
"Great quick stay. Close to Mohegan. Food options on the same road."
Alicia 1-night trip
Posted 3 days ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Marina Bay Cottages

Marina Bay Cottages

10/10 Excellent
"Great place to stay and enjoy the area . Very clean and quiet"
Kevin 3-night trip
Posted 3 days ago
Marina Bay Cottages

More cheap accommodation in Chester

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT
NZ$125
1 Sept - 2 Sept
includes taxes & fees
7.4/10 Good! (1,009 reviews)
Motel 6 New Haven - Branford, CT
Days Inn by Wyndham Berlin Meriden

Days Inn by Wyndham Berlin Meriden

2387 Berlin Turnpike Berlin CT
NZ$142
14 Sept - 15 Sept
includes taxes & fees
Days Inn by Wyndham Berlin Meriden
Red Roof Inn Meriden

Red Roof Inn Meriden

10 Bee St Meriden CT
NZ$150
31 Aug - 1 Sept
includes taxes & fees
7.4/10 Good! (1,006 reviews)
Red Roof Inn Meriden
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

1954 Norwich New London Tpke Montville CT
NZ$153
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (2,007 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
NZ$187
10 Sept - 11 Sept
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

2253 Berlin Tpke Berlin CT
NZ$204
23 Aug - 24 Aug
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
Best Western Plus New England Inn & Suites

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester is perfect for nature lovers, offering national parks and beautiful beaches for exploration.
  • Charming Downtown: Stroll through the quaint downtown, filled with friendly locals and a welcoming vibe.
  • Cultural Scene: Enjoy live music, local theatre, and opera for a vibrant evening out.
  • Romantic Getaways: Experience stunning scenery ideal for couples seeking a relaxing escape.
  • Varied Accommodations: Choose from inviting hotels and delightful bed & breakfasts, catering to all traveller needs.

Find great hotels near Chester

Explore the charming town of Chester, Connecticut, where a variety of accommodation options await you, including inviting hotels and delightful bed & breakfasts. Whether you're seeking pet-friendly lodging, amenities for business travel, or an adventurous getaway, Chester has something to suit every traveller's needs. Discover local gems like the Thistle Inn and read reviews to find the best fit for your stay in this picturesque New England destination.

  • Baymont by Wyndham Branford/New Haven: This budget-friendly hotel is ideal for the adventurous traveller, located 25.7km from Chester. Baymont offers a range of exciting activities nearby, such as skydiving, ziplining, and boat tours, making it a fantastic choice for families and those seeking outdoor fun. The hotel is also pet-friendly, accommodating furry companions with specific policies for pets. Families will appreciate the amenities tailored for children, including complimentary cribs and a welcoming atmosphere for younger guests, ensuring a memorable stay for all.
  • Red Roof Inn Meriden: A budget-friendly lodging option located 27.4km from Chester, Red Roof Inn Meriden caters to business travellers and pet owners alike. This hotel permits dogs and cats, allowing guests to bring their beloved pets along for the journey. With a focus on convenience and comfort, the inn provides essential amenities for business needs, making it a practical choice for those travelling for work. The welcoming atmosphere and straightforward service make it a reliable option for those seeking an uncomplicated stay.
  • Sleep Inn & Suites Niantic North: Situated 24.1km from Chester, Sleep Inn & Suites Niantic North offers a comfortable and family-friendly environment, boasting a solid guest rating of 8.4 out of 10. This budget-friendly hotel features amenities designed for children, such as free cribs and window guards for safety, catering to families on the go. With a focus on providing a restful experience, guests can enjoy well-appointed rooms and essential services that make it an excellent choice for both family vacations and business trips.

Where to stay near Chester

Chester, Connecticut, offers a delightful escape for those seeking outdoor adventures and romantic scenery. Stroll through the charming downtown, where friendly locals and family-friendly vibes create a welcoming atmosphere. Enjoy a weekend getaway amidst the beauty of New England, exploring picturesque landscapes and quaint neighbourhoods. Don't miss the chance to soak in the serene surroundings and vibrant community spirit that make Chester a perfect destination for relaxation and exploration.

  • Old Saybrook: Situated a mere 14.5km from Chester, Old Saybrook is a charming coastal city that offers a delightful blend of outdoor activities and scenic beauty. Renowned for its romantic atmosphere, visitors flock here during the warmer months from June to August. The area boasts stunning beaches and the picturesque landscapes of the nearby national state park, making it a perfect spot for family outings and leisurely strolls. Popular venues like golf courses and resorts provide plenty of options for relaxation and recreation, ensuring an enjoyable travel experience.
  • Westbrook: Located just 12.9km away from Chester, Westbrook is another lovely coastal destination that captivates visitors with its natural beauty and vibrant atmosphere. The city experiences moderate seasonal travel, peaking in the summer months. Westbrook is particularly known for its romantic settings and outdoor adventures, with local beaches and engaging music concerts drawing visitors in. With a variety of resorts and an event conference venue, it's an excellent choice for couples and families seeking both relaxation and entertainment.
  • Deep River: A close 4.8km from Chester, Deep River is a quaint city that offers a serene escape with its stunning natural surroundings. The visitor traffic remains stable throughout the year, with peaks in April and the summer months. Deep River is perfect for those seeking outdoor experiences, featuring recreational areas and a local theatre for cultural events. The proximity to a beautiful lake and the national state park allows for ample exploration, while its scenic beauty creates a romantic backdrop for visitors looking to unwind.

Things to do near Chester

Shopping

In Chester, you can enjoy local shops along Main Street, featuring unique gifts and souvenirs. If you're up for a drive, head to the nearby Westbrook Outlets for a wider selection of brands at discounted prices.

Recreation

Enjoy a rejuvenating escape at the Spa at Saybrook Point, where you can indulge in soothing treatments and relax by the scenic waterfront. For outdoor fun, explore the nearby Chester Creek Preserve with its picturesque walking trails, ideal for a refreshing stroll amidst nature.

Adventure

Waterford Speedbowl is a thrilling motor racing venue located 25.7km from Chester. Experience the excitement of high-speed races and the vibrant atmosphere that surrounds this adrenaline-fueled locale, perfect for motorsport enthusiasts seeking an exhilarating day out.

Nightlife

In Chester, the historic downtown offers charming pubs like The River Tavern, where you can enjoy local brews and live music. For a relaxed vibe, head to The Gelston House, which features stunning river views and a cosy atmosphere, perfect for unwinding after a day of exploring.

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

Find the best attractions near Chester

Chester is perfect for outdoor and romantic getaways, boasting stunning scenery and a range of attractions. Visitors can explore national parks, beautiful beaches, and lovely parks that cater to adventure-seekers and nature lovers alike. For a fulfilling experience, consider getting a Chester map and planning your visit to Chester, CT, to make the most of your stay in this charming town.

  • Harvey's Beach: Located a mere 16.1km from Chester, Harvey's Beach offers a picturesque shoreline where you can soak up the sun and enjoy the relaxing beach vibes. It's an ideal spot for leisurely strolls and taking in the scenic coastal views.
  • Major General Joseph Spencer Memorial: Just 6.4km away, this monument commemorates the contributions of Major General Joseph Spencer during the Revolutionary War. With its cultural significance, it's an insightful visit for history enthusiasts and those interested in local heritage.
  • Crystal Lake Town Park: Situated 12.9km from Chester, this urban park provides a family-friendly environment with ample outdoor space for picnics, play, and relaxation. Enjoy the serene surroundings while engaging in recreational activities.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageAverage
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

Flying into Chester, Connecticut, is convenient with three major airports nearby. New York's JFK Airport is located 138.4km away, with upscale hotels like The William Vale and Arlo Williamsburg both situated 17.7km from the airport. LaGuardia Airport, also in New York, is 135.2km from Chester, featuring luxurious accommodation options such as Hilton Club The Quin and The Plaza, both around 5-9.7km from the airport. For those preferring a closer option, Hartford's Bradley International Airport is just 61.2km away, with good hotel choices like DoubleTree by Hilton Hartford only 1.6km from the terminal, making it easy to access Chester for your vacation.

Frequently asked questions

What is the best area to stay in Chester?
The best area to stay in Chester, Connecticut, is the village centre.This charming area is the heart of Chester, known for its quaint Main Street lined with independent shops, art galleries, and restaurants. It's very walkable, with historic buildings and a relaxed, welcoming feel. You'll find the iconic Chester Package Store and The Pattaconk 1850 Bar & Grille right on Main Street, serving as local landmarks.Couples looking for a peaceful and romantic getaway will find the village centre perfect. You can enjoy strolls along the picturesque streets, browse local artisan shops, and dine at excellent restaurants, all within easy walking distance. The proximity to the scenic Connecticut River also offers opportunities for quiet relaxation or a leisurely boat trip.For solo travellers seeking a tranquil escape with a touch of local character, the village centre is also an excellent choice. You can easily explore the unique boutiques, enjoy a coffee at a local café, or simply unwind in a pleasant setting.
When is the best time to go to Chester?
The best time to visit Chester, Connecticut, is during the spring and autumn months, specifically from May to June and September to October. These periods offer pleasant weather and a wealth of activities.Spring in Chester brings mild temperatures, typically ranging from 10°C to 20°C, and the town's natural beauty comes alive with blooming flowers and lush greenery. It's an excellent time for outdoor activities like hiking along the Pattaconk Brook or exploring the serene Cockaponset State Forest. Many local art galleries and shops also begin extending their hours, making it ideal for those who appreciate browsing unique local crafts.Autumn provides a different but equally stunning experience, with temperatures generally between 10°C and 18°C. The region is famous for its spectacular fall foliage, turning the Connecticut River Valley into a canvas of reds, oranges, and yellows. This is a prime time for scenic drives along Route 148 or taking a relaxing cruise on the Connecticut River, offering unparalleled views of the changing leaves. Local farms also celebrate the harvest season with special events.While July and August are also warm and sunny, with temperatures often exceeding 25°C, they can be quite busy with summer holidaymakers.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 can I save on a hotel booking in Chester with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Chester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chester?
Prices for hotels in Chester often vary, but you can find a great deal from NZ$125 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 our cheapest rates.

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