Hotels in Chester

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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, (149 reviews)
Escape to these charming cabins in East Haddam with convenient kitchenettes and peaceful patios. Just minutes from Machimoodus State Park and Amasa Day House, this retreat offers free parking and climate control for a comfortable outdoor adventure.
The price is $118
$182 total
includes taxes & fees
Jun 9 - Jun 10
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Copper Beech Inn
Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (511 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
May 12 - May 13
Copper Beech Inn
Clinton Motel
Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (309 reviews)
Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.
The price is $76
$87 total
includes taxes & fees
May 12 - May 13
Clinton Motel
Lamplighter Motel - Clinton, Connecticut
Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (233 reviews)
The price is $69
$79 total
includes taxes & fees
May 12 - May 13
Lamplighter Motel - Clinton, Connecticut
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, (1,007 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 $91
$104 total
includes taxes & fees
May 17 - May 18
Pier Blue Inn Old Saybrook - Essex
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, (473 reviews)
This Old Saybrook motel combines convenience with comfort, just minutes from the train station. Enjoy room service after exploring nearby Tanger Outlets, then unwind in the garden. Each room includes helpful amenities like refrigerators and microwaves.
The price is $81
$93 total
includes taxes & fees
May 17 - May 18
Econo Lodge Inn & Suites Old Saybrook Westbrook
Liberty Inn
Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (646 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 $92
$106 total
includes taxes & fees
May 17 - May 18
Liberty Inn
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,007 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
May 31 - Jun 1
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, (917 reviews)
Tranquil accommodations near Tanger Outlets and Crystal Lake Town Park offer a quiet escape. Take advantage of free weekend breakfast, WiFi, and parking. Only a 4-minute drive from Old Saybrook Station for convenient regional travel.
The price is $83
$98 total
includes taxes & fees
May 14 - May 15
Super 8 by Wyndham Old Saybrook
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (191 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
May 18 - May 19
Westbrook Inn B&B
The Scranton Seahorse Inn
The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (242 reviews)
The price is $306
$339 total
includes taxes & fees
May 12 - May 13
The Scranton Seahorse Inn
The Captain Stannard
The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (263 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 $234
$260 total
includes taxes & fees
May 21 - May 22
The Captain Stannard
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,002 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
May 20 - May 21
Water's Edge Resort & Spa
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, (243 reviews)
Experience coastal charm at this Guilford hotel with complimentary WiFi and parking. Located near the Hyland House and Henry Whitfield State Museums, the hotel offers 24-hour front desk service and is just a short drive from Guilford Station for easy regional travel.
The price is $89
$103 total
includes taxes & fees
May 12 - May 13
Tower Inn And Suites Of Guilford - Madison
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,002 reviews)
Immerse yourself in scenic coastal views at this tranquil waterfront resort featuring 2 outdoor pools, an indoor pool, and indulgent spa treatments. The on-site Fresh Salt restaurant and convenient marina create a perfect setting near Fort Saybrook Monument Park.
The price is $349
$426 total
includes taxes & fees
Jun 7 - Jun 8
Saybrook Point Resort & Marina
Spark by Hilton Guilford
Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (123 reviews)
Tranquil seaside accommodation near Hyland House Museum offers free breakfast, WiFi, and parking. Explore local hiking paths or visit Henry Whitfield State Museum, just minutes from Guilford Station. Guests love the helpful staff and clean, quiet rooms.
The price is $119
$136 total
includes taxes & fees
May 14 - May 15
Spark by Hilton Guilford
Solano Inn
Solano Inn
2.5 star property
Portland
8.6 out of 10, Excellent, (230 reviews)
This Portland hotel offers 24-hour front desk service near popular attractions like Dart Island State Park. Enjoy complimentary WiFi and parking during your Connecticut getaway, with convenient access to Berlin Station just a short drive away.
The price is $103
$118 total
includes taxes & fees
May 12 - May 13
Solano Inn
The Homestead
The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (92 reviews)
Experience waterfront charm at this Madison B&B, 6 minutes from the train station. Enjoy hiking trails, kayaking, and complimentary perks like daily continental breakfast, bike rentals, and WiFi. The helpful staff receives consistent praise from fellow travelers.
The price is $438
$486 total
includes taxes & fees
May 12 - May 13
The Homestead
The Bevin House Bed & Breakfast
The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (84 reviews)
The price is $305
$339 total
includes taxes & fees
May 13 - May 14
The Bevin House Bed & Breakfast
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (369 reviews)
Bask in coastal luxury at this Madison Beach Hotel with a private shoreline along the Connecticut coast. Enjoy American cuisine at The Wharf restaurant, rejuvenate at the full-service spa, or admire adjacent golf course views. Nearby attractions and helpful staff enhance your seaside getaway.
The price is $347
$399 total
includes taxes & fees
May 25 - May 26
Madison Beach Hotel
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.

Top neighborhoods in Chester

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

Learn more about Chester

Chester is well-known for its attractions such as Connecticut River and Norma Terris Theater.

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

Check out reviews of Chester hotels guests love

Frequently asked questions

What hotels do travelers like in Chester?
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.