Find hotels in Chester, CT from AED 262

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Chester hotels

1. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (530 reviews)
"Nice stay. Quite,"
United States
Joseph
The price is AED 1,025
AED 1,178 total
includes taxes & fees
8 Nov - 9 Nov
Copper Beech Inn

2. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,003 reviews)
"The staff gave us good recommendations for places to eat and things to do"
United States
Susan
The price is AED 356
AED 409 total
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Old Saybrook - Westbrook

3. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (220 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AED 466
AED 705 total
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

4. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,005 reviews)
"Beautiful setting, good food, friendly staff. Will definitely stay again"
United States
cynthia
The price is AED 598
AED 751 total
includes taxes & fees
12 Nov - 13 Nov
Water's Edge Resort & Spa

5. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (347 reviews)
"Loved this place. Perfect for a one night stay. What I loved most though, was how clean and fresh the linens were."
United States
Kalev
The price is AED 286
AED 329 total
includes taxes & fees
8 Nov - 9 Nov
Clinton Motel

6. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (205 reviews)
"This place is always the best love the rooms. The staff is excellent place is so clean always feel so comfortable here."
United States
Diane
The price is AED 1,089
AED 1,208 total
includes taxes & fees
10 Nov - 11 Nov
Westbrook Inn B&B

7. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,009 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
United States
Kevin
The price is AED 285
AED 328 total
includes taxes & fees
8 Nov - 9 Nov
Pier Blue Inn Old Saybrook - Essex

8. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,001 reviews)
"Location was amazing and restaurant was great"
United States
Jenny
The price is AED 988
AED 1,265 total
includes taxes & fees
18 Nov - 19 Nov
Saybrook Point Resort & Marina

9. Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
9.0 out of 10, Wonderful, (233 reviews)
"This place was clean, and the staff were friendly and helpful. Breakfast was good and overall, we were comfortable and impressed."
United States
LAURETTA
The price is AED 334
AED 384 total
includes taxes & fees
29 Nov - 30 Nov
Spark by Hilton Guilford

10. Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (688 reviews)
"Nice place to stay."
United States
Maria Victoria
The price is AED 280
AED 321 total
includes taxes & fees
8 Dec - 9 Dec
Liberty Inn

11. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (286 reviews)
"An excellent choice for our brief stay in Old Saybrook. Clean, comfortable and very well maintained."
United States
Siegfried
The price is AED 859
AED 954 total
includes taxes & fees
8 Nov - 9 Nov
The Captain Stannard

12. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.4 out of 10, Exceptional, (252 reviews)
"A lovely stay at a classic New England B & B. Perfect location for a visit to Madison."
United States
Tracy
The price is AED 863
AED 957 total
includes taxes & fees
9 Nov - 10 Nov
The Scranton Seahorse Inn

13. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.6 out of 10, Exceptional, (398 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
The price is AED 991
AED 1,140 total
includes taxes & fees
23 Nov - 24 Nov
Madison Beach Hotel

14. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (113 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is AED 790
AED 877 total
includes taxes & fees
9 Nov - 10 Nov
The Homestead

15. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (504 reviews)
"My stay was easy I was able to get a good nights sleep. The room was clean and the location gives good access to anything I may need"
United States
Robert
The price is AED 263
AED 302 total
includes taxes & fees
15 Nov - 16 Nov
Econo Lodge Inn & Suites Old Saybrook Westbrook

16. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
2.0 star property
Old Saybrook
6.8 out of 10, (955 reviews)
"If you want a third world experience next to the railroad this is your place!"
United States
David
The price is AED 233
AED 268 total
includes taxes & fees
11 Nov - 12 Nov
Motel 6 Old Saybrook, CT

17. Solano Inn

Solano Inn
2.5 star property
Portland
8.4 out of 10, Very good, (289 reviews)
"Very nice place to stay."
United States
Douglas
The price is AED 333
AED 382 total
includes taxes & fees
8 Nov - 9 Nov
Solano Inn

18. Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
8.8 out of 10, Excellent, (680 reviews)
"We only stayed one night but were very happy with everything. Clean, great staff and very comfortable. Wish there might have been an option for continental breakfast included but the restaurant on the premises looked very nice too."
United States
Wendy
The price is AED 567
AED 726 total
includes taxes & fees
8 Dec - 9 Dec
Inn at Middletown

19. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (264 reviews)
"Rooms were clean and bed very comfortable. For a one nite stay , it was the perfect motel with a reasonable cost. I would stay there again"
United States
John
The price is AED 253
AED 291 total
includes taxes & fees
8 Nov - 9 Nov
Lamplighter Motel - Clinton, Connecticut

20. Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.8 out of 10, Exceptional, (1,004 reviews)
"Breakfast off a menu and cooked to order was a lovely surprise!"
United States
Lillian
The price is AED 584
AED 672 total
includes taxes & fees
1 Dec - 2 Dec
Inn at Harbor Hill Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in Chester

Find the best Chester areas and neighborhoods 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

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.

A calm lake surrounded by vibrant autumn foliage.

Top Chester Hotel Reviews

Find out more about Chester

Top reasons to visit Chester

  • Outdoor Adventures: Chester boasts beautiful state parks and charming beaches, perfect for hiking, swimming, and enjoying nature.
  • Charming Downtown: Explore the picturesque downtown area filled with friendly locals, vibrant shops, and delightful eateries.
  • Live Performances: Enjoy live music, local theater, and opera performances that showcase Chester's rich cultural scene.
  • Romantic Getaways: The scenic landscapes and serene parks make Chester an ideal spot for couples seeking a romantic escape.
  • Diverse Accommodations: From cozy bed and breakfasts to comfortable hotels, Chester offers a range of lodging options to suit all travelers.

Find great hotels near Chester

Discover a range of lodging options in Chester, Connecticut, from charming bed and breakfasts to comfortable hotels. Whether you're traveling for business or seeking a pet-friendly adventure, Chester offers accommodations that cater to your needs. Explore the local attractions, read reviews, and find the perfect place to relax after a day of exploring, including popular spots like the Thistle Inn and various hotels in the Chester area.

  • Baymont by Wyndham Branford/New Haven: Located 26km from Chester, Baymont by Wyndham Branford/New Haven is ideal for families and adventure seekers. This budget-friendly hotel offers a range of outdoor activities nearby, including ziplining, skydiving, and hiking, ensuring an exciting stay. The property is pet-friendly, accommodating your furry friends with specific policies in place. Families will appreciate the amenities for children, including free cribs and child-safety features. With its focus on adventure and family-friendly services, this hotel is a great choice for those looking to create lasting memories.
  • Red Roof Inn Meriden: Situated 27km from Chester, Red Roof Inn Meriden is a budget-friendly option perfect for business travelers and pet owners. The property allows pets in rooms, featuring a straightforward pet policy that includes waived fees for service animals. Guests can enjoy convenient access to local business hubs while still having the comfort of a welcoming environment for their pets. This hotel combines practicality with comfort, making it a solid choice for those traveling for work or leisure with their companions.
  • Sleep Inn & Suites Niantic North: Just 24km from Chester, Sleep Inn & Suites Niantic North is a well-rated budget hotel, offering a family-friendly atmosphere with a guest rating of 8.4 out of 10. This accommodation caters to both families and business travelers, with complimentary cribs and child safety features like window guards available. Guests can enjoy a comfortable stay with modern amenities that ensure a restful experience. Its convenient location and focus on family needs make it a suitable option for those looking to relax and unwind.

Where to stay near Chester

Chester, Connecticut, offers a charming escape for outdoor enthusiasts and romantic getaways alike. Explore the picturesque downtown area, where friendly people and vibrant shops create a welcoming atmosphere. Experience the beauty of New England's scenic landscapes while enjoying family-friendly activities. Whether you're planning a weekend getaway or simply soaking in the local culture, Chester's unique charm promises a memorable vacation filled with adventure and relaxation.

  • East Haddam: East Haddam is a charming city located 10km from Chester, offering a delightful blend of outdoor activities and scenic beauty. This destination attracts visitors moderately throughout the year, with peak travel times in April and from July to August. East Haddam is perfect for a romantic getaway or for those seeking adventure in nature. The city is home to the renowned Goodspeed Opera House and various recreational areas, providing a vibrant cultural scene. Nature lovers will appreciate the nearby lake and the expansive state park, making it an ideal spot for hiking, picnicking, and enjoying breathtaking views.
  • Cobalt: Situated 19km from Chester, Cobalt is a quaint city that welcomes travelers year-round, with peak seasons occurring in July to August and October. Known for its outdoor experiences and picturesque scenery, Cobalt is perfect for couples looking for a romantic escape. The city hosts lively music concerts and has several educational venues, making it a great place for both relaxation and enrichment. Visitors can enjoy the local lake and nearby beach, along with various resorts that offer a perfect retreat to unwind and connect with nature.
  • Old Saybrook: Located 14km from Chester, Old Saybrook is a vibrant coastal city that attracts visitors throughout the year, especially from June to August. This charming destination is celebrated for its outdoor activities and stunning scenery, making it a favorite for romantic getaways. Old Saybrook features beautiful recreational areas, golf courses, and luxurious resorts, providing ample opportunities for relaxation and leisure. With its pristine beaches and proximity to the national state park, visitors can indulge in sunbathing, swimming, and exploring the natural wonders of the region.

Things to do near Chester

Shopping

Chester offers charming local shops like The Chester Package Store and The Peach Pit for unique gifts and souvenirs. If you're up for a drive, visit the nearby Clinton Crossing Premium Outlets for a wider selection of brands and discounts.

Recreation

The Spa at the Saybrook Point Inn offers a tranquil setting with a variety of treatments, including massages and facials, designed to rejuvenate the body and mind. For outdoor enthusiasts, the nearby Chester Creek offers scenic trails for walking and biking, surrounded by beautiful natural landscapes.

Adventure

At Waterford Speedbowl, located 26km from Chester, you can immerse yourself in the exhilarating world of motor racing. Experience the thrill of high-speed races and the vibrant atmosphere filled with adrenaline and excitement, making it a must-visit for adventure enthusiasts.

Nightlife

In Chester, the Rusty Rail Tavern offers a cozy atmosphere with live music and a vibrant bar scene. Nearby, the Chester Fairgrounds hosts seasonal events, adding local flair to your nightlife experience. For a laid-back vibe, you can enjoy craft cocktails at the nearby River Tavern.

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

Booking tips and Expedia advantages for Chester

To save money during your trip to Chester, Connecticut, consider visiting from December to February when hotel prices are lower, especially on Tuesdays. Utilize Expedia’s search tool to find budget-friendly accommodations by sorting prices from lowest to highest and filtering for eco-friendly options. Combining your hotel stay with flights and activities in an Expedia package can lead to additional savings. Explore free local attractions and use public transportation to keep travel expenses down. Avoid weekends, particularly Saturdays, for more affordable rates.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are December to February, 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 enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservations in Chester with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Connecticut offers a perfect blend of outdoor activities and romantic scenery, making it an ideal vacation spot. You can explore beautiful state parks, charming beaches, and serene parks, catering to those seeking adventure and natural beauty. For a comprehensive experience, consider using a Chester map and plan your visit to fully enjoy the local attractions and activities in and around this picturesque town.

  • Essex Island Marina: Located 10km from Chester, Essex Island Marina offers a vibrant atmosphere with adventure and outdoor activities. Enjoy boating, kayaking, or simply soaking up the sun while taking in stunning views of the Connecticut River.
  • Guilford Town Green: About 21km away, this eco-friendly park provides a serene space for families to gather. The lush greenery, walking paths, and local events create a welcoming environment perfect for picnics or leisurely strolls.
  • Giants Neck Beach: Situated 24km from Chester, Giants Neck Beach boasts a relaxing beach vibe. It's an inviting spot for sunbathing, swimming, and beachcombing along the picturesque shoreline.

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.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
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

Traveling to Chester, Connecticut, is convenient with several nearby airports. New York's JFK Airport is 138km away, with excellent hotel options such as The William Vale and Arlo Williamsburg, both 18km from the airport. LaGuardia Airport, located 135km from Chester, offers luxurious stays at The Plaza, A Fairmont Hotel and The Times Square EDITION, both just 10km away. Hartford's Bradley International Airport is the closest at 61km, with comfortable accommodations like the DoubleTree by Hilton Hartford and Marriott Hartford Downtown, located 2km and 19km away, respectively. All these airports provide efficient access to Chester and its attractions.

Frequently Asked Questions

What are some of the best vacation home rentals in Chester?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Chester is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For more details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.

Where is the best hotel to stay with easy access to Norma Terris Theater?

Riverwind Inn Bed & Breakfast is one of the top choices for your stay based on our traveler data, and this 3-star B&B offers free breakfast and free parking. It's located 1.8 mi (2.9 km) from Norma Terris Theater. Other good options within a few miles include Boardman House Inn and The Old Sindelar Farm.

What are some accommodations with pools in Chester?

Regency Inn & Suites New London, Mystic: Features a snack bar/deli, an indoor pool, and buffet. Hyatt Place Uncasville - Casino Area and Water's Edge Resort & Spa are a couple of other choices that offer an onsite pool. View all hotels with pools in Chester.

What's the best accommodation near Tweed - New Haven Regional Airport (HVN)?

Quality Inn East Haven - New Haven is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.3 mi (2.1 km) from Tweed - New Haven Regional Airport. Other good options close to the airport include La Quinta Inn & Suites by Wyndham New Haven and Omni New Haven Hotel at Yale.

How is it to stay in Chester?

Visitors can enjoy all that Chester has to offer including the waterfront, parks, and theaters. In Chester, there are 5 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

Favorite places to visit include Connecticut River, Chester Creek Marina, and Norma Terris Theater. Additionally, you might want to add Connecticut Valley Railroad State Park Trail to your itinerary. Check out what more to see and do in Expedia's Chester guide.

What's the seasonal weather like in Chester?

The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Chester is 54 inches.

What's the best place for a stay in Chester?

Regency Inn & Suites New London, Mystic, located 19.1 mi (30.8 km) from the heart of Chester, is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Hyatt Place Uncasville - Casino Area. See all available top hotels, or vacation rentals in Chester.

Explore a world of travel with Expedia