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

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Our top choices for Chester hotels

1. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,010 reviews)
"Beautiful setting, good food, friendly staff. Will definitely stay again."
United States
cynthia
2 days ago
$208 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
Water's Edge Resort & Spa

2. Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area
3.0 star property
Montville
9.0 out of 10, Wonderful, (2,808 reviews)
"Had amazing breakfast. Was very pleased with stay. Convenient to go to casino this way."
United States
Mary
1 day ago
$110 nightly
The price is $127
Nov 4 - Nov 5
Total with taxes and fees
Hyatt Place Uncasville - Casino Area

3. Mohegan Sun

Mohegan Sun
4.5 star property
Montville
9.2 out of 10, Wonderful, (1,842 reviews)
"Friendly and helpful staff everywhere. Concert venues was great. Bed very comfortable."
United States
Jeannine
10 days ago
Mohegan Sun

4. 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, (1,000 reviews)
"Room was clean and staff was helpful, accommodated my check in after midnight."
United States
Neal
10 days ago
$82 nightly
The price is $94
Nov 8 - Nov 9
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex

5. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
"Great ocean sounds through the pen window!"
United States
Eric
6 days ago
$183 nightly
The price is $209
Nov 23 - Nov 24
Total with taxes and fees
Sound View Greenport

6. Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area
2.5 star property
Montville
8.6 out of 10, Excellent, (2,097 reviews)
"Nice hotel located close to casinos. Breakfast was good. Room was clean."
United States
Mary
19 hours ago
$88 nightly
The price is $101
Nov 2 - Nov 3
Total with taxes and fees
Microtel Inn & Suites by Wyndham Uncasville Casino Area

7. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (530 reviews)
"Restaurant was nice. Rooms were nice. Staff was great in restaurant."
United States
Laurie
September 13th, 2026
$279 nightly
The price is $321
Oct 29 - Oct 30
Total with taxes and fees
Copper Beech Inn

8. New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven
9.2 out of 10, Wonderful, (2,400 reviews)
"Overall, the hotel is nice."
United States
Rob
2 days ago
$132 nightly
The price is $152
Nov 28 - Nov 29
Total with taxes and fees
New Haven Hotel

9. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,004 reviews)
"The rooms are great. This is a great place to stay."
United States
MaryAnn
2 days ago
$97 nightly
The price is $111
Nov 18 - Nov 19
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook

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

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
3.0 star property
Montville
9.2 out of 10, Wonderful, (1,052 reviews)
"The hotel was wonderful. The room was nice."
United States
Matthew
3 days ago
$134 nightly
The price is $154
Nov 8 - Nov 9
Total with taxes and fees
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

11. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (285 reviews)
"Clean, comfortable and very well maintained."
United States
Siegfried
15 days ago
$213 nightly
The price is $237
Nov 8 - Nov 9
Total with taxes and fees
The Captain Stannard

12. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,007 reviews)
"Beautiful resort with really nice large rooms. Perfect location on the Sound."
United States
David
7 days ago
$309 nightly
The price is $356
Nov 3 - Nov 4
Total with taxes and fees
Saybrook Point Resort & Marina

13. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (205 reviews)
"I love our breakfast anf the coffee."
United States
Carole
26 days ago
$296 nightly
The price is $329
Oct 29 - Oct 30
Total with taxes and fees
Westbrook Inn B&B

14. Old Lyme Inn

Old Lyme Inn
3.5 star property
Old Lyme
9.2 out of 10, Wonderful, (187 reviews)
"The room was very clean. We were in room 4 on the first floor."
United States
Lisa
8 days ago
Old Lyme Inn

15. The Capitol Hotel

The Capitol Hotel
3.0 star property
Downtown Hartford
7.2 out of 10, Good, (1,611 reviews)
"We stayed there for 1 night. The location was good."
United States
Allyson
5 days ago
$93 nightly
The price is $107
Nov 28 - Nov 29
Total with taxes and fees
The Capitol Hotel

16. Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
4.0 star property
Downtown New Haven
8.8 out of 10, Excellent, (1,107 reviews)
"Nice place to stay. All staff were very helpful. It was in the perfect spot."
United States
Jessica
1 day ago
$161 nightly
The price is $185
Nov 1 - Nov 2
Total with taxes and fees
Omni New Haven Hotel at Yale

17. Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (687 reviews)
"Room was clean. Shower was good."
United States
Adam
August 10th, 2026
$99 nightly
The price is $114
Oct 29 - Oct 30
Total with taxes and fees
Liberty Inn

18. Higganum House B&B

Higganum House B&B
3.0 star property
Higganum
9.6 out of 10, Exceptional, (5 reviews)
"Convenient drive to several fabulous venues for live theatre Goodspeed Opera House."
United States
Fausta
July 18th, 2026
Higganum House B&B

19. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (344 reviews)
"Room was super spacious. Front desk staff were friendly. Great value for a short stay."
United States
Brittany
17 days ago
$78 nightly
The price is $90
Nov 1 - Nov 2
Total with taxes and fees
Clinton Motel

20. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (348 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
16 days ago
$210 nightly
The price is $237
Nov 11 - Nov 12
Total with taxes and fees
The Shoals Suites and Slips
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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.

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.

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.

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.

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.

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

More cheap stays in Chester

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 $80 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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