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Our top choices for Chester hotels

Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
Discover this charming B&B in Old Saybrook, offering free breakfast with local cuisine, WiFi, and parking. Located near General William Hart House and Katharine Hepburn Cultural Arts Center, it provides easy access to regional attractions.
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
The price is ￥55,537
￥61,646 total
includes taxes & fees
Dec 20 - Dec 21
James Pharmacy Bed & Breakfast
Breakfast and dinner served
Copper Beech Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (506)
Located near Ivoryton Playhouse, this charming hotel offers deep-tissue massages and complimentary breakfast. Enjoy drinks at the bar, stroll through the garden, or unwind on the terrace after exploring Museum of Fife and Drum.
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is ￥43,382
￥49,889 total
includes taxes & fees
Dec 14 - Dec 15
Copper Beech Inn
Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1000)
Overlooking the harbor in Niantic, this charming B&B offers free breakfast, WiFi and parking. Explore the area using complimentary bike rentals or try nearby hiking trails and kayaking. The terrace provides a peaceful spot to enjoy marina views after a day of adventures.
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is ￥24,723
￥28,431 total
includes taxes & fees
Dec 14 - Dec 15
Inn at Harbor Hill Marina
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
Enjoy seaside charm at this welcoming Westbrook Inn B&B, offering complimentary full breakfast and bicycle rentals. Near Westbrook Town Beach and Tanger Outlets, with hiking trails, a snack bar, and terrace for relaxation. Includes free WiFi and parking.
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is ￥33,132
￥36,777 total
includes taxes & fees
Dec 14 - Dec 15
Westbrook Inn B&B
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1000)
Immerse yourself in coastal tranquility at this Old Saybrook retreat, where 3 pools, marina access, and spa services create a peaceful haven. The waterfront Fresh Salt restaurant complements stunning views just minutes from the train station.
"Excellent food, in addition to friendly and helpful staff."
United States
marybeth
The price is ￥45,645
￥56,379 total
includes taxes & fees
Dec 22 - Dec 23
Saybrook Point Resort & Marina
Exterior
Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (341)
Embrace seaside tranquility at this beach hotel featuring American cuisine at The Wharf restaurant and rejuvenating spa services. Adjacent to a golf course with private beach access, fitness center, and bar. Near Deacon John Grave House and Madison Station.
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is ￥38,201
￥43,931 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Madison Beach Hotel
Property grounds
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
Wake up to tranquility at this peaceful Old Saybrook hotel where highway noise won't disturb your rest. Explore nearby Ferry Landing State Park, shop at the antique village, or enjoy kayaking adventures. Free WiFi and convenient self parking enhance your Connecticut getaway.
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is ￥12,455
￥14,323 total
includes taxes & fees
Dec 14 - Dec 15
Liberty Inn
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters
The Homestead

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (89)
This enchanting Madison B&B delights with complimentary continental breakfast and WiFi. Explore nearby hiking trails using free bike rentals, or try kayaking adventures. Located near Madison Station with helpful staff and convenient parking for local attractions.
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
United States
Cynthia
The price is ￥41,721
￥46,311 total
includes taxes & fees
Dec 17 - Dec 18
The Homestead
Seasonal outdoor pool, pool umbrellas, sun loungers
The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (81)
Located near Day Pond State Park, this Victorian B&B offers a seasonal outdoor pool and hiking trails. Enjoy complimentary breakfast, WiFi, and parking while exploring the area from this charming retreat with attentive staff.
"The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. "
United States
Juliette
The price is ￥37,522
￥41,650 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Bevin House Bed & Breakfast
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
Located near Clinton Plaza Shopping Center, this waterfront motel provides complimentary parking and WiFi. Take a refreshing dip in the outdoor pool before exploring nearby attractions or enjoy a short walk to Clinton Station for convenient regional travel.
"Great staff and clean rooms"
United States
Tyler
The price is ￥12,128
￥13,947 total
includes taxes & fees
Dec 15 - Dec 16
Clinton Motel
Property grounds
The Spa at Norwich Inn

The Spa at Norwich Inn

The Spa at Norwich Inn
3.5 star property
Norwich
8.8 out of 10, Excellent, (1001)
Escape to this historic hotel featuring a full-service spa offering deep-tissue massages and aromatherapy. Enjoy 2 restaurants, a fitness center, and serene atmosphere near Mohegan Sun Arena, with attentive staff ensuring a peaceful getaway.
"Great place!"
United States
Jill
The Spa at Norwich Inn
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
Enjoy the historic atmosphere of this Westbrook B&B with complimentary breakfast, WiFi, and parking. Explore local hiking trails or borrow bikes to visit Westbrook Town Beach and Tanger Outlets. The garden terrace offers a peaceful retreat after adventurous days.
"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
Exterior
Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG

Holiday Inn New London - Mystic Area by IHG
3.0 star property
New London
8.4 out of 10, Very Good, (1002)
Located minutes from Garde Arts Center and the ferry dock, this hotel offers an indoor pool and La Luna Restaurant. Rooms include refrigerators and microwaves. Enjoy free WiFi and parking while the quiet atmosphere and helpful staff ensure a restful stay.
"Room was great, Staff was awesome."
United States
Bryan
The price is ￥12,439
￥14,305 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn New London - Mystic Area by IHG
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (89)
Tucked away in East Haddam, these cabins offer peaceful retreats with convenient kitchenettes and private patios. Explore nearby Machimoodus State Park or visit Amasa Day House while enjoying free parking and climate control.
"Clean and good service."
United States
Simge
The price is ￥18,503
￥28,431 total
includes taxes & fees
Dec 18 - Dec 19
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Free daily continental breakfast
Springhill Suites by Marriott Mystic Waterford

Springhill Suites by Marriott Mystic Waterford

Springhill Suites by Marriott Mystic Waterford
3.0 star property
Quaker Hill
8.6 out of 10, Excellent, (921)
This tranquil Springhill Suites offers a refreshing indoor pool and 24-hour fitness center. Located within 15 minutes of Mystic Aquarium and Seaport, with Connecticut College Arboretum nearby. Free breakfast, WiFi and parking enhance your stay.
"The staff were friendly and helpful."
United States
JOHN
The price is ￥19,436
￥22,352 total
includes taxes & fees
Dec 21 - Dec 22
Springhill Suites by Marriott Mystic Waterford
Exterior
Tower Inn And Suites Of Guilford - Madison

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, (233)
Located near Hyland House Museum and Henry Whitfield State Museum, this comfortable hotel offers convenient amenities including free WiFi, complimentary parking, and 24-hour front desk service. Guilford Station is just a 5-minute drive away.
"Clean, convenient, quiet place run by nice folks. We’d stay here again."
United States
Lisa
The price is ￥13,915
￥16,002 total
includes taxes & fees
Dec 14 - Dec 15
Tower Inn And Suites Of Guilford - Madison
Front of property - evening/night
Oakdell Motel

Oakdell Motel

Oakdell Motel
2.5 star property
Waterford
7.0 out of 10, Good, (100)
Situated in Waterford, this motel offers complimentary WiFi and parking just minutes from Regal Waterford and Crystal Mall. Guests enjoy a 24-hour front desk while Mohegan Sun Casino and Ocean Beach Park are within a short drive.
"The room was spotless. Great location and price for going to Moheghan Sun."
United States
Steven
The price is ￥15,076
￥18,659 total
includes taxes & fees
Dec 14 - Dec 15
Oakdell Motel
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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, (460)
Situated near a train station, this motel offers practical amenities like in-room refrigerators and microwaves. Enjoy the outdoor terrace and garden spaces while staying close to Chalker Beach and Tanger Outlets with complimentary parking and WiFi.
"🙂"
United States
Jared
The price is ￥10,422
￥11,985 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Exterior
Rodeway Inn Waterford - New London

Rodeway Inn Waterford - New London

Rodeway Inn Waterford - New London
2.0 star property
Waterford
8.2 out of 10, Very Good, (773)
Experience peaceful stays at this quiet Waterford motel with complimentary WiFi and parking. Take a dip in the seasonal outdoor pool after exploring nearby Crystal Mall and Regal Waterford attractions. Previous guests consistently praise the helpful staff and clean accommodations.
"I have stayed here a couple of times and have enjoyed the clean room and professional staff. "
United States
Carolyn
The price is ￥12,424
￥14,288 total
includes taxes & fees
Dec 17 - Dec 18
Rodeway Inn Waterford - New London
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1004)
Escape to this Westbrook retreat featuring a private beach with umbrellas, 3 restaurants including Italian cuisine at Dattilo's, and rejuvenating spa treatments. The indoor pool and hot tub complement free WiFi and parking near Tanger Outlets.
"Holiday family tradition!"
United States
Donald
The price is ￥26,072
￥32,665 total
includes taxes & fees
Dec 17 - Dec 18
Water's Edge Resort & Spa
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

Chester Creek Marina

Explore the waterfront in Chester with a trip to Chester Creek Marina. While you're in the area, stroll along the beautiful beaches.
See properties

Norma Terris Theater

You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.
See properties

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.

See all hotels in Chester
Connecticut River Autumn Landscape with the view of landmark architectures on the woodland hill, a tranquil New England scenery

Top Chester Hotel Reviews

Mohegan Sun

Mohegan Sun

10/10 Excellent
"Everything"
Louis 2-night trip
Posted 3 days ago
Mohegan Sun

More cheap stays in Chester

Red Roof Inn Mystic - New London

Red Roof Inn Mystic - New London

707 Colman Street, Building A New London CT
The price is ￥8,395 per night from Dec 21 to Dec 22
￥8,395
￥9,654 total
Dec 21 - Dec 22
includes taxes & fees
5.6/10 (1,000 reviews)

Frequently asked questions

What's the best place for a stay in Chester?
Mohegan Sun, located 21 mi (33.7 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 Microtel Inn & Suites by Wyndham Uncasville Casino Area and Hyatt Place Uncasville - Casino Area. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation home rentals in Chester?
Thames River Retreat · CT College+Casinos+USCGA: This vacation home rental near Chester is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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?
Mohegan Sun: Resort, 15-minute walk from Mohegan Sun Casino. Features 19 restaurants, 2 indoor pools, and a full-service spa. Hyatt Place Uncasville - Casino Area and Holiday Inn Norwich by IHG 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 7 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, Norma Terris Theater, and Connecticut Valley Railroad State Park Trail. Additionally, you might want to add Chester Creek Marina 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.

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