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

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Our top choices for Chester hotels

1. 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, (218 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is £143
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. 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, (1,006 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
United States
Kevin
The price is £70
includes taxes & fees
10 Nov - 11 Nov
Pier Blue Inn Old Saybrook - Essex

3. 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 £83
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Old Saybrook - Westbrook

4. 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 £67
includes taxes & fees
9 Nov - 10 Nov
Clinton Motel

5. 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 £152
includes taxes & fees
12 Nov - 13 Nov
Water's Edge Resort & Spa

6. Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
9.0 out of 10, Wonderful, (228 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 £78
includes taxes & fees
29 Nov - 30 Nov
Spark by Hilton Guilford

7. 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 £54
includes taxes & fees
10 Nov - 11 Nov
Motel 6 Old Saybrook, CT

8. 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 £238
includes taxes & fees
12 Nov - 13 Nov
Copper Beech Inn

9. 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 £65
includes taxes & fees
6 Dec - 7 Dec
Liberty Inn

10. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,000 reviews)
"Location was amazing and restaurant was great"
United States
Jenny
The price is £242
includes taxes & fees
7 Dec - 8 Dec
Saybrook Point Resort & Marina

11. 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, (503 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 £61
includes taxes & fees
12 Nov - 13 Nov
Econo Lodge Inn & Suites Old Saybrook Westbrook

12. 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 £59
includes taxes & fees
9 Nov - 10 Nov
Lamplighter Motel - Clinton, Connecticut

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 £230
includes taxes & fees
23 Nov - 24 Nov
Madison Beach Hotel

14. Tower Inn And Suites Of Guilford - Madison

Tower Inn And Suites Of Guilford - Madison
2.5 star property
Guilford
7.4 out of 10, Good, (261 reviews)
"Hotel looked very nice both inside and outside room was clean bathroom had everything we needed nice location for what we were there for. McDonalds,Wendy's and target nearby. Nice experience."
United States
Teresa
The price is £63
includes taxes & fees
7 Nov - 8 Nov
Tower Inn And Suites Of Guilford - Madison

15. Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.8 out of 10, Exceptional, (1,002 reviews)
"Beautiful property overlooking the water with delicious breakfast every morning. Loved our stay there!"
United States
Margarita
The price is £136
includes taxes & fees
1 Dec - 2 Dec
Inn at Harbor Hill Marina

16. 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 £77
includes taxes & fees
8 Nov - 9 Nov
Solano Inn

17. 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 £193
includes taxes & fees
9 Nov - 10 Nov
The Scranton Seahorse Inn

18. 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 £193
includes taxes & fees
8 Nov - 9 Nov
The Captain Stannard

19. Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
8.8 out of 10, Excellent, (679 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 £148
includes taxes & fees
7 Dec - 8 Dec
Inn at Middletown

20. Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
2.5 star property
Niantic
9.0 out of 10, Wonderful, (628 reviews)
"Good location and nice shower. The eggs for breakfast are pretty rough though."
United States
Brianna
The price is £81
includes taxes & fees
24 Nov - 25 Nov
Best Western Niantic - New London/Mystic Area
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.
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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

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.

A calm lake surrounded by vibrant autumn foliage.

Top Chester Hotel Reviews

More cheap stays in Chester

Find out more about Chester

Top reasons to visit Chester

  • Picturesque Downtown: Stroll through Chester's charming downtown, lined with quaint shops and eateries, where friendly locals welcome visitors.
  • Outdoor Adventures: Enjoy hiking and outdoor activities in the stunning natural beauty of New England, including national and state parks.
  • Cultural Experiences: Immerse yourself in Chester's vibrant culture with live music, local theatre, and unmissable events.
  • Historic Sites: Explore captivating historic houses that reflect the town's rich heritage.
  • Diverse Accommodation: Choose from charming bed and breakfasts to well-equipped hotels, catering to all preferences and needs.

Find great hotels near Chester

Discover a delightful array of accommodation options in Chester, Connecticut, ranging from charming bed and breakfasts to well-equipped hotels. Whether you're seeking a pet-friendly stay or facilities catering to business travellers, Chester has something to suit your needs. Unwind in comfortable seating areas, explore local attractions, and enjoy authentic reviews of Chester's hotels to ensure your stay is both enjoyable and memorable.

  • Red Roof Inn Meriden: Red Roof Inn Meriden is an economical choice for travellers seeking a convenient and comfortable stay. Located 27.4km from Chester, this property stands out as a pet-friendly option, making it ideal for those wishing to bring their furry companions along. With amenities that cater to business travellers and leisure seekers alike, guests can enjoy a relaxed atmosphere with essential services. The hotel's pet policy is accommodating, featuring variable fees based on pet size and type, ensuring a welcoming environment for both you and your pets.
  • Baymont by Wyndham Branford/New Haven: Situated 25.7km from Chester, Baymont by Wyndham Branford/New Haven is a budget-friendly hotel perfect for adventurous families and pet lovers. This property offers a range of exciting activities, including nearby skydiving, ziplining, and hiking, ensuring that guests of all ages have plenty of opportunities for fun. The hotel is also equipped with amenities specifically for children, such as complimentary cribs, making it a family-friendly choice. With a flexible pet policy, it welcomes your four-legged friends, offering a comfortable stay for everyone.
  • Sleep Inn & Suites Niantic North: Located 24.1km from Chester, Sleep Inn & Suites Niantic North boasts a commendable guest rating of 8.4 out of 10, making it an appealing option for families and business travellers. The hotel provides a range of child-friendly amenities, including window guards and free cribs, ensuring a safe and comfortable environment for younger guests. Its budget-friendly nature combined with thoughtful services makes it an excellent choice for those looking to enjoy a hassle-free stay while exploring the area.

Where to stay near Chester

Chester, Connecticut, offers a delightful blend of outdoor charm and romantic scenery, making it an ideal weekend getaway. Stroll through the picturesque downtown area, where friendly locals welcome you to explore quaint shops and eateries. Immerse yourself in the natural beauty of New England, with opportunities for hiking and enjoying scenic views. Whether you seek family-friendly activities or a tranquil escape, Chester’s inviting atmosphere promises a memorable experience for all visitors.

  • Westbrook: Located a mere 12.9km from Chester, Westbrook is a delightful seaside town that captivates visitors with its stunning coastal scenery and outdoor activities. The town is particularly popular during the summer months, attracting those seeking romantic getaways and family-friendly beach experiences. You can enjoy a variety of activities, including relaxing at the beach, attending music concerts, or playing a round of golf at one of the local courses. With its charming resorts and vibrant waterfront, Westbrook offers a perfect blend of relaxation and entertainment for all travellers.
  • Old Saybrook: Situated 14.5km from Chester, Old Saybrook is a picturesque town that boasts a rich history and beautiful landscapes. This destination attracts visitors year-round, with peak times during the summer. Outdoor enthusiasts will revel in the scenic views and recreational opportunities, including access to stunning beaches and a nearby national state park. Enjoy a leisurely stroll through the town's parks, play golf, or unwind at a resort. Old Saybrook's quaint charm and vibrant atmosphere make it an ideal spot for a romantic escape or a family outing.
  • Deep River: Just 4.8km from Chester, Deep River is a charming town that enchants visitors with its scenic beauty and outdoor opportunities. The town attracts a steady stream of travellers, particularly in the spring and summer months. Here, you can explore local lakes, enjoy recreational areas, or catch a performance at the local theatre. With its proximity to a national state park and beautiful beaches, Deep River is perfect for those seeking adventure in nature or a peaceful retreat. The town's welcoming atmosphere and natural allure make it a must-visit destination.

Things to do in Chester

Chester, Connecticut, offers a delightful blend of outdoor adventures and romantic scenery, perfect for a memorable getaway. Explore its charming recreational areas, enjoy live music, and indulge in the local theatre and opera scene. Don’t miss the sightseeing tours and unmissable events that showcase the town’s vibrant culture, making every moment a joyous experience. Whether you’re seeking fun activities or a peaceful retreat, Chester has something for everyone.

Shopping

In Chester, you can explore charming local shops like The Bowerbird for unique gifts and The Chester Mercantile for souvenirs. If you're up for a drive, consider visiting the Clinton Crossing Premium Outlets for a wider selection of brands and bargains, located about 19.3km away.

Recreation

Experience rejuvenation at The Spa at Saybrook Point, where you can indulge in luxurious treatments and unwind by the serene waterfront. For outdoor relaxation, explore the scenic trails of the nearby Chester Creek Preserve, perfect for a leisurely stroll amidst nature's beauty.

Adventure

Explore the picturesque Chester Creek, where you can kayak through tranquil waters while enjoying scenic views of the surrounding nature. For hiking enthusiasts, the nearby Cockaponset State Forest offers diverse trails amidst beautiful woodlands, perfect for an adventurous day out.

Nightlife

Experience the vibrant nightlife in Chester by visiting the Rustic Barn for a casual atmosphere and hearty pub fare. For cocktails, head to The River Tavern, where you can enjoy scenic views alongside expertly crafted drinks. Don’t miss the live music at The Chester Meeting House for a lively evening.

*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: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Connecticut, is an idyllic destination for outdoor enthusiasts seeking romantic scenery. Visitors can explore captivating sites such as national and state parks, picturesque beaches, and historic houses. For those eager to immerse themselves in the local charm, consider visiting Chester itself and utilising a Chester map to navigate its delightful offerings. Whether you seek adventure or serene landscapes, Chester promises a memorable experience.

  • Harvey's Beach: Located 16.1km from Chester, Harvey's Beach offers a quintessential beach experience with its sandy shores and relaxing vibes. It's a perfect spot for sunbathing, swimming, or enjoying a leisurely stroll along the water's edge.
  • Essex Island Marina: Just 9.7km from Chester, Essex Island Marina is an adventurer's paradise. With opportunities for boating, kayaking, and exploring the surrounding coastal beauty, it combines outdoor excitement with a vibrant beach atmosphere.
  • Chaffinch Island State Park: Situated 22.5km from Chester, Chaffinch Island State Park is a hidden gem known for its friendly locals and serene environment. Ideal for a budget-friendly getaway, this park invites visitors to relax, picnic, and appreciate nature.

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.

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

For your visit to Chester, Connecticut, you can conveniently fly into several major airports. New York's JFK Airport is located 138.4km away, with top hotels such as the 5-star Arlo Williamsburg and The William Vale, both situated 17.7km from the airport. Similarly, LaGuardia Airport is 135.2km from Chester, featuring luxury options like The Plaza - A Fairmont Managed Hotel, just 8.0km away. Alternatively, Hartford's Bradley International Airport is only 61.2km from Chester, offering nearby accommodations such as the 4-star DoubleTree by Hilton, just 1.6km from the airport. Each airport provides transportation services to and from these hotels for your convenience.

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 cafƩ, 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, 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 £55 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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