Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Where to stay in Chester?

Property grounds

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, (1,004 reviews)
Tucked beside Old Saybrook Station, this peaceful inn offers comfortable beds and free parking. Explore nearby Chalker Beach or hike local trails before relaxing in clean rooms. Himalaya Café and The Teakettle Cafe are just steps away for tasty meals.
The price is $104
$120 total
includes taxes & fees
Aug 4 - Aug 5
Pier Blue Inn Old Saybrook - Essex
Bar (on property)

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,009 reviews)
Relax at this coastal Westbrook resort with a private beach, 3 restaurants including Italian cuisine at Dattilo's Fine Dining, and rejuvenating spa services. Near Tanger Outlets and just 9 minutes from Old Saybrook Station.
The price is $249
$304 total
includes taxes & fees
Aug 31 - Sep 1
Water's Edge Resort & Spa
Lobby sitting area

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area
3.0 star property
Montville
9.0 out of 10, Wonderful, (2,724 reviews)
Steps from Mohegan Sun Casino and Arena, this hotel offers an indoor pool, 24-hour fitness center, and bar/lounge. Enjoy free breakfast, WiFi, and parking. Guests praise the comfortable beds and helpful staff.
The price is $105
$121 total
includes taxes & fees
Aug 10 - Aug 11
Hyatt Place Uncasville - Casino Area
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (672 reviews)
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
The price is $350
$486 total
includes taxes & fees
Aug 18 - Aug 19
Sound View Greenport
Lobby sitting area

New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven
9.2 out of 10, Wonderful, (2,240 reviews)
A short walk to Yale, this hotel offers a fitness center and business-friendly amenities. Quiet rooms provide peaceful stays, while the lobby cafe and nearby restaurants give you dining options. Comfortable beds and free WiFi make your New Haven visit even more pleasant.
The price is $144
$165 total
includes taxes & fees
Aug 9 - Aug 10
New Haven Hotel
Breakfast and dinner served

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (520 reviews)
Escape to this tranquil hotel near the train station, where deep-tissue massages and elegant dining await. Explore Ivoryton Playhouse and Museum of Fife and Drum nearby, then unwind in the garden or terrace with a drink from the bar.
The price is $279
$321 total
includes taxes & fees
Aug 3 - Aug 4
Copper Beech Inn
Room, 1 Queen Bed, Non Smoking | In-room safe, desk, laptop workspace, blackout drapes

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, (1,990 reviews)
Just 5 minutes from Mohegan Sun Casino and Arena, this hotel offers a free continental breakfast daily. Enjoy complimentary wifi and parking during your stay. Foxwoods Resort Casino and Grand Theater are a short drive away.
The price is $78
$90 total
includes taxes & fees
Aug 17 - Aug 18
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Lobby

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,000 reviews)
Relax at this peaceful hotel with an indoor pool and fitness center. Just a short drive from Old Saybrook Station, enjoy American cuisine at The Comfort Cafe and unwind at the bar. Free breakfast, WiFi, and parking add value near popular local attractions.
The price is $118
$136 total
includes taxes & fees
Aug 23 - Aug 24
Quality Inn Old Saybrook - Westbrook
Property amenity

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, (1,014 reviews)
Crisp, modern rooms await at this Uncasville hotel just 5 minutes from Mohegan Sun Casino and Arena. Energize with complimentary breakfast, then swim in the indoor pool or hit the fitness center before exploring nearby New London's attractions.
The price is $125
$144 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (201 reviews)
Escape to this charming seaside B&B offering free full breakfast, WiFi, and parking. Borrow bikes to explore nearby hiking trails or visit Westbrook Town Beach and Tanger Outlets. A terrace and snack bar add comfort to your coastal getaway.
The price is $323
$358 total
includes taxes & fees
Aug 17 - Aug 18
Westbrook Inn B&B
Exterior

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (310 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
The price is $413
$497 total
includes taxes & fees
Aug 3 - Aug 4
The Shoals Suites and Slips
Property grounds

Old Lyme Inn

Old Lyme Inn
3.5 star property
Old Lyme
9.2 out of 10, Wonderful, (177 reviews)
Old Lyme Inn
Living area

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (273 reviews)
Start your day with a delicious continental breakfast at this Georgian bed & breakfast near Westbrook Town Beach. Enjoy hiking trails, kayaking, or ride complimentary bikes to explore. Tanger Outlets and convenient parking add to this peaceful coastal retreat.
The price is $260
$289 total
includes taxes & fees
Aug 4 - Aug 5
The Captain Stannard
2 indoor pools, open 6 AM to 10 PM, cabanas (surcharge), pool umbrellas

Mohegan Sun

Mohegan Sun
4.5 star property
Montville
9.2 out of 10, Wonderful, (1,900 reviews)
Escape to this luxury resort with an onsite casino and golf course, just steps from Mohegan Sun Arena. Unwind at the spa, splash in 2 indoor pools, or dine at Todd English's Tuscany serving Italian cuisine. Enjoy free WiFi and parking during your stay.
The price is $229
$288 total
includes taxes & fees
Aug 6 - Aug 7
Mohegan Sun
Property grounds

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (666 reviews)
Experience peaceful slumber in this quiet hotel near Essex Saybrook Antique Village. Minutes from Ferry Landing State Park, the hotel provides free WiFi and parking. Nearby kayaking adventures and attentive staff create a refreshing coastal getaway.
The price is $99
$114 total
includes taxes & fees
Aug 3 - Aug 4
Liberty Inn
Breakfast and brunch served

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
4.0 star property
Downtown New Haven
8.6 out of 10, Excellent, (1,061 reviews)
Stylish sanctuary in downtown New Haven with panoramic city views from upper floors. Just a 15-minute walk from Yale and 7 minutes from State Street Station, this hotel offers 2 restaurants and 24-hour fitness center for busy travelers.
The price is $142
$163 total
includes taxes & fees
Aug 24 - Aug 25
Omni New Haven Hotel at Yale
Frette Italian sheets, premium bedding, down comforters, pillowtop beds

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (633 reviews)
Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.
The price is $391
$498 total
includes taxes & fees
Aug 19 - Aug 20
The Harbor Front Inn
Desk, laptop workspace, blackout drapes, iron/ironing board

The Capitol Hotel

The Capitol Hotel
3.0 star property
Downtown Hartford
7.4 out of 10, Good, (1,450 reviews)
The price is $124
$143 total
includes taxes & fees
Aug 2 - Aug 3
The Capitol Hotel
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (95 reviews)
Perched on the bay, this coastal retreat offers a private beach, outdoor pool, and spa with hydrotherapy treatments. The seasonal restaurant serves local cuisine while proximity to Crescent Beach and Sunset Beach enhances your island getaway.
The price is $623
$784 total
includes taxes & fees
Aug 24 - Aug 25
The Pridwin Hotel
Interior

Higganum House B&B

Higganum House B&B
3.0 star property
Higganum
9.6 out of 10, Exceptional, (4 reviews)
Higganum House B&B
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.
View all properties

Top neighborhoods in Chester

A plate of food with three square pieces topped with greens and caviar.
Photo by Annette Babek
Open Photo by Annette Babek

Chester Center

The Chester Center neighborhood has lots to see including Norma Terris Theater and Connecticut Valley Railroad State Park Trail.

Top landmarks in Chester

Chester Creek Marina

Imagine strolling along Chester Creek Marina for some great waterfront pics. It's located 2.8 mi (4.5 km) from central Chester.
See properties

Learn more about Chester

Chester is well-known for its attractions such as Connecticut River and Chester Creek Marina.

See all hotels in Chester
A historic waterfront estate with a large white building featuring a balcony and a flagpole.

Check out reviews of Chester hotels guests love

Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

8/10 Good
"Is good"
Jhenny 1-night trip
Posted 4 hours ago
Regency Inn & Suites New London, Mystic

Frequently asked questions

What hotels do travelers like in Chester?
Guests like Pier Blue Inn Old Saybrook - Essex, Water's Edge Resort & Spa and Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy.
Can I book refundable accommodations in Chester?
If you need the flexibility to change your plans to Chester, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Chester be like during my vacation?
July and August are typically the warmest months in Chester when the average temp is 70°F. January and February are the coldest months when the average temperature is 35°F. October and December are the months with the most rain.
Why should I book my Chester accommodation with Hotels.com?
There are plenty of reasons to book your Chester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.