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Our top choices for Chester hotels

Fairfield by Marriott Inn & Suites Wallingford New Haven

Fairfield by Marriott Inn & Suites Wallingford New Haven
3.0 star property
Wallingford
8.8 out of 10, Excellent, (1,001 reviews)
"Always stay here when visting family in CT."
United States
David
The price is CA $157
CA $181 total
includes taxes & fees
Apr 2 - Apr 3
Fairfield by Marriott Inn & Suites Wallingford New Haven

Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
3.0 star property
Wallingford
9.0 out of 10, Wonderful, (928 reviews)
"Very clean, had all we needed. The front desk staff was great."
United States
Scott
The price is CA $163
CA $187 total
includes taxes & fees
Apr 5 - Apr 6
Homewood Suites by Hilton Wallingford-Meriden

Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
3.0 star property
Wallingford
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean rooms, staff was great"
United States
Jackie
The price is CA $157
CA $180 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Wallingford/Meriden

Courtyard New Haven Wallingford

Courtyard New Haven Wallingford
3.0 star property
Wallingford
8.8 out of 10, Excellent, (792 reviews)
"Clean room, friendly staff!"
United States
Julie
The price is CA $168
CA $193 total
includes taxes & fees
Mar 12 - Mar 13
Courtyard New Haven Wallingford

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (229 reviews)
"Would stay again. "
United States
pamela
The price is CA $89
CA $102 total
includes taxes & fees
Mar 8 - Mar 9
Lamplighter Motel - Clinton, Connecticut

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, (467 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is CA $91
CA $105 total
includes taxes & fees
Mar 11 - Mar 12
Econo Lodge Inn & Suites Old Saybrook Westbrook

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (303 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is CA $107
CA $123 total
includes taxes & fees
Mar 24 - Mar 25
Clinton Motel

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is CA $138
CA $159 total
includes taxes & fees
Mar 11 - Mar 12
Quality Inn Old Saybrook - Westbrook

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook
2.0 star property
Old Saybrook
7.0 out of 10, Good, (913 reviews)
"Excellent "
United States
David
The price is CA $102
CA $121 total
includes taxes & fees
Apr 1 - Apr 2
Super 8 by Wyndham Old Saybrook

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,002 reviews)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is CA $388
CA $481 total
includes taxes & fees
Mar 23 - Mar 24
Saybrook Point Resort & Marina

Baymont by Wyndham Branford/New Haven

Baymont by Wyndham Branford/New Haven
2.5 star property
Branford
6.6 out of 10, (1,001 reviews)
"Good Breakfast, nice atmosphere "
United States
Jessie
The price is CA $135
CA $155 total
includes taxes & fees
Mar 8 - Mar 9
Baymont by Wyndham Branford/New Haven

Branford Motel

Branford Motel
2.0 star property
Branford
5.2 out of 10, (153 reviews)
"The room was very clean "
United States
Kathyn
The price is CA $102
CA $118 total
includes taxes & fees
Mar 7 - Mar 8
Branford Motel

Rodeway Inn Waterford - New London

Rodeway Inn Waterford - New London
2.0 star property
Waterford
8.2 out of 10, Very good, (782 reviews)
"The room was clean and the staff member was very friendly. No complaints. Nice accommodations for the price."
United States
Vanessa
The price is CA $105
CA $121 total
includes taxes & fees
Mar 15 - Mar 16
Rodeway Inn Waterford - New London

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (260 reviews)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT
2.0 star property
Branford
7.2 out of 10, Good, (1,004 reviews)
"The motel is clean, employees are very polite, helpful and the room was very spacious."
United States
Arianna
The price is CA $90
CA $105 total
includes taxes & fees
Mar 10 - Mar 11
Motel 6 New Haven - Branford, CT

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (641 reviews)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is CA $112
CA $128 total
includes taxes & fees
Mar 12 - Mar 13
Liberty Inn

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, (1,003 reviews)
"Room was clean and warm and the staff was very friendly "
United States
Pattie
Pier Blue Inn Old Saybrook - Essex

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is CA $412
CA $458 total
includes taxes & fees
Apr 1 - Apr 2
James Pharmacy Bed & Breakfast

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (179 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is CA $281
CA $312 total
includes taxes & fees
Mar 11 - Mar 12
Westbrook Inn B&B

Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG
3.0 star property
Westside Norwich
7.6 out of 10, Good, (1,014 reviews)
"Clean room, easy check-in/out, friendly staff"
United States
Tracy
The price is CA $132
CA $152 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Norwich by IHG
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 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 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.

Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery

Top Chester Hotel Reviews

Recent Reviews in Chester

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Hotels in Chester with star rating

Find out more about Chester

Top reasons to visit Chester

  • Scenic Outdoor Adventures: Chester offers beautiful state parks and beaches, perfect for hiking, picnicking, and relaxation by the water.
  • Charming Downtown: Explore the quaint downtown area filled with friendly locals, unique shops, and delightful eateries.
  • Cultural Attractions: Visit the Chester Historical Museum and catch a show at the local theatre for a taste of the town's heritage.
  • Romantic Getaways: Ideal for couples, Chester's picturesque scenery and cozy accommodations create a romantic atmosphere.
  • Family-Friendly Environment: With a variety of activities and attractions, Chester ensures a memorable experience for visitors of all ages.

Find great hotels near Chester

Discover charming hotel accommodations in Chester, Connecticut, ideal for every type of traveller. Whether you're seeking a cozy bed & breakfast or a versatile hotel with business facilities, Chester offers a range of options. Enjoy pet-friendly services, perfect for those travelling with furry companions, and embrace a delightful beach vacation experience. With various star-rated hotels in the area, your stay in this quaint town promises comfort and convenience.

  • Extended Stay America Suites Hartford Meriden: Tailored for business travellers, Extended Stay America Suites Hartford Meriden offers a comfortable and convenient stay just 27.4km from Chester. This hotel is pet-friendly, welcoming both dogs and cats, making it ideal for those travelling with furry companions. With essential amenities designed for work, including a business centre and complimentary Wi-Fi, guests can stay productive during their visit. The property also provides a home-like experience with fully equipped kitchens in each suite, allowing guests to prepare their own meals while enjoying a comfortable atmosphere.
  • Baymont by Wyndham Branford/New Haven: Situated 25.7km from Chester, Baymont by Wyndham Branford/New Haven is perfect for families and adventure seekers alike. Offering a range of exciting activities such as hiking, ziplining, and boat tours nearby, this hotel encourages guests to explore the great outdoors. The property is also pet-friendly, with amenities catering to children, including complimentary cribs. With a welcoming atmosphere and engaging recreational options, it’s an excellent choice for those looking to create lasting memories with their loved ones.
  • Red Roof Inn Meriden: Located 27.4km from Chester, Red Roof Inn Meriden is a welcoming spot for business travellers and the LGBTQIA community. This pet-friendly hotel boasts a supportive environment and offers essential business amenities, ensuring guests can work comfortably during their stay. With a focus on inclusivity and comfort, the property provides a relaxed atmosphere where everyone feels at home. Enjoy the convenience of bringing your pets along while taking advantage of the excellent facilities designed for both leisure and work.

Where to stay near Chester

Chester, Connecticut, offers a delightful blend of outdoor adventures and romantic scenery, making it an ideal getaway for Canadian travellers. Explore the charming downtown filled with friendly locals, and take in the beautiful spots and scenic views along the Connecticut shoreline. Nearby beaches provide a perfect backdrop for relaxation, while the area's family-friendly atmosphere ensures a memorable experience for all. Whether you're seeking adventure or tranquility, Chester has something for everyone.

  • Old Saybrook: Located 14.5km from Chester, Old Saybrook is a charming city that offers visitors a delightful blend of outdoor adventure and scenic beauty. Known for its romantic atmosphere, this destination is perfect for couples and families alike. The peak travel season runs from June to August, with a variety of attractions to explore, including beautiful beaches and picturesque lakes. Outdoor enthusiasts can enjoy recreational areas, while golf courses and music concerts add to the vibrant local scene. Don't miss the opportunity to witness stunning sunsets along the shoreline.
  • Westbrook: Just 12.9km from Chester, Westbrook is a delightful coastal city that draws visitors with its scenic views and outdoor activities. The city experiences a moderate seasonal influx of tourists, particularly from June to August. Westbrook is known for its romantic charm, making it an ideal getaway for couples. Popular activities include relaxing at the beach, attending music concerts, and enjoying the local resorts. The family-friendly atmosphere, combined with event and conference venues, makes Westbrook a fantastic destination for both leisure and business travellers.
  • Madison: Situated 14.5km from Chester, Madison is a picturesque city that attracts visitors seeking adventure and stunning scenery. With a moderately seasonal tourism pattern, peak travel occurs during the summer months. Madison is ideal for outdoor lovers, featuring recreational areas, golf courses, and music concerts. The proximity to beautiful beaches and the national state park makes it a perfect spot for nature enthusiasts. Madison's inviting atmosphere, coupled with its family-friendly beaches, ensures that it offers memorable experiences for all ages.

Things to do near Chester

Chester, Connecticut, is perfect for outdoor and romantic getaways, offering beautiful scenery and a variety of activities. Visitors can enjoy the local recreational areas, catch a show at the theatre, and explore educational attractions. Don't miss the steam train experience and other top sites that highlight the charm of this quaint town. Chester promises a delightful blend of relaxation and adventure for all who visit.

Shopping

Experience shopping in Chester with local gems like the Sundial Herb Garden, just 8.0km away. For more options, visit Clinton Crossing Premium Outlets and North Madison Shopping Center, both 12.9km away, offering a mix of family-friendly vibes and diverse shops.

Recreation

At Devil’s Hopyard State Park, enjoy serene hiking trails and tranquil picnic spots surrounded by nature. For golf enthusiasts, both Banner Country Club and Fox Hopyard Golf Club offer picturesque courses with vibrant outdoor settings, perfect for a relaxing day of sport and fresh air.

Adventure

Experience thrilling winter sports at Powder Ridge Mountain Park and Resort, a premier ski destination located 24.1km from Chester. For adrenaline-pumping excitement, visit Waterford Speedbowl, a vibrant motor racing venue 25.7km away. Explore the natural beauty at Cromwell Meadows Wildlife Management Area, also 25.7km from Chester.

Nightlife

Experience the enchanting atmosphere at the Goodspeed Opera House, just 6.4km away, where you can enjoy captivating performances. For a thrilling adventure, visit Brownstone Exploration & Discovery Park, 24.1km out, or gaze at the stars at Van Vleck Observatory, located 16.4km from Chester.

*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 on your trip to Chester, Connecticut, consider visiting between December and February for lower accommodation rates, avoiding peak months like May and July to August. Booking your stay on a Tuesday can also lead to better deals compared to Saturday. Use Expedia to compare hotel options and refine your choices based on your budget. Don't forget to explore package deals that combine flights, hotels, and activities for additional savings. Seek out free local attractions and public transportation options to enhance your experience without stretching your wallet.

  • 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: Utilize Expedia's search tool to refine your choices based on your budget, desired location, and preferred type of accommodation. To find the best 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 perfect for a romantic getaway or an outdoor adventure, featuring scenic spots like state parks, beaches, and historic houses. Visitors can explore the Chester Historical Museum and enjoy the charming atmosphere of Chester, CT. With a variety of attractions catering to those seeking adventure and beautiful scenery, Chester offers an unforgettable vacation experience.

  • Essex Steam Train: Experience the charm of this railway museum located 8.0km from Chester. Board a vintage steam train and enjoy a scenic ride through the picturesque Connecticut River Valley, immersing yourself in the rich history and culture of the area.
  • Gillette Castle State Park: Just 4.8km from Chester, this unique national park features a stunning castle with breathtaking views. Explore the beautiful hiking trails, picnic areas, and the captivating scenery that showcases the region’s natural beauty and adventure.
  • Essex Island Marina: Situated 9.7km from Chester, this marina offers a delightful blend of outdoor activities and beach vibes. Enjoy kayaking, paddleboarding, or simply relaxing by the water while soaking in the vibrant atmosphere of the marina.

Best time to go to Chester

The best time to visit Chester is dependant 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 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

When visiting Chester, Connecticut, you have several major airports to consider. Bradley International Airport (BDL) in Hartford is the closest, situated 61.2km away. Nearby accommodations include the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and the 4-star Marriott Hartford Downtown, located 19.3km away. T.F. Green Airport (PVD) in Providence is 95.0km from Chester, with options like the Omni Providence Hotel and Graduate by Hilton Providence, both 11.3km from PVD. Alternatively, MacArthur Airport (ISP) in Islip is 85.3km away, with nearby hotels such as the Hyatt Regency Long Island and Jake's 58 Casino Hotel, both only 6.4km from ISP.

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, 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 can I save on a Chester hotel booking with Expedia?
Members always get our best prices. Find our best Chester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 CA $105 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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