Hotels in Chester
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Copper Beech Inn
Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (506)
8.6/10
Excellent
(506)
- Charming inn by Ivoryton Playhouse offers massage therapy and garden views.
The price is $279
$279
$321 total
includes taxes & fees
Jan 6 - Jan 7
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, (98)
9.6/10
Exceptional
(98)
- Rustic cabin getaway near Machimoodus State Park with patios and kitchenettes.
The price is $101
$101
$162 total
includes taxes & fees
Jan 11 - Jan 12
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (178)
9.8/10
Exceptional
(178)
- Oceanside B&B near Westbrook Town Beach with complimentary breakfast and bikes.
The price is $206
$206
$228 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1003)
7.8/10
Good
(1003)
- Stay in a quiet, convenient hotel near Old Saybrook Station with a refreshing pool.
The price is $97
$97
$111 total
includes taxes & fees
Jan 11 - Jan 12
Liberty Inn
Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
7.4/10
Good
(640)
- Tranquil retreat near Old Saybrook, offering serene rest despite highway proximity.
The price is $80
$80
$92 total
includes taxes & fees
Jan 19 - Jan 20
Clinton Motel
Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (299)
8.6/10
Excellent
(299)
- Oceanfront escape in Clinton with seasonal pool and complimentary amenities.
The price is $76
$76
$87 total
includes taxes & fees
Jan 6 - Jan 7
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, (465)
7.2/10
Good
(465)
- A cozy coastal hideaway near the railway, offering refreshing terrace views.
The price is $67
$67
$77 total
includes taxes & fees
Jan 11 - Jan 12
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, (1002)
8.0/10
Very Good
(1002)
- Walk to local dining spots near train station with quiet, peaceful atmosphere.
The price is $74
$74
$85 total
includes taxes & fees
Jan 6 - Jan 7
Super 8 by Wyndham Old Saybrook
Super 8 by Wyndham Old Saybrook
2.0 star property
Old Saybrook
7.0 out of 10, Good, (910)
7.0/10
Good
(910)
- Enjoy a peaceful retreat in Old Saybrook with complimentary amenities and nearby attractions.
The price is $74
$74
$88 total
includes taxes & fees
Jan 6 - Jan 7
Lamplighter Motel - Clinton, Connecticut
Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (228)
6.4/10
(228)
The price is $65
$65
$75 total
includes taxes & fees
Jan 6 - Jan 7
The Captain Stannard
The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
9.8/10
Exceptional
(259)
- Serene Georgian B&B offers coastal charm with a garden terrace and bicycle rentals.
The price is $238
$238
$264 total
includes taxes & fees
Feb 3 - Feb 4
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1005)
8.8/10
Excellent
(1005)
- Savor this New England escape with waterfront dining and private beach access.
The price is $229
$229
$281 total
includes taxes & fees
Jan 6 - Jan 7
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1011)
9.6/10
Exceptional
(1011)
- Waterfront retreat with resort pools and a full-service marina in Old Saybrook.
The price is $309
$309
$380 total
includes taxes & fees
Jan 8 - Jan 9
The Homestead
The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91)
10/10
Exceptional
(91)
- Take a short drive to Madison Station from this B&B near trails and kayaking.
The price is $313
$313
$347 total
includes taxes & fees
Jan 11 - Jan 12
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, (237)
7.4/10
Good
(237)
- Cozy Connecticut stay near historic museums with free parking and WiFi.
The price is $89
$89
$103 total
includes taxes & fees
Jan 6 - Jan 7
Spark by Hilton Guilford
Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (77)
8.8/10
Excellent
(77)
- Discover a peaceful oceanside retreat with hiking trails and complimentary perks.
The price is $103
$103
$118 total
includes taxes & fees
Jan 31 - Feb 1
Solano Inn
Solano Inn
2.5 star property
Portland
8.8 out of 10, Excellent, (215)
8.8/10
Excellent
(215)
- Discover comfort minutes from Arrigoni Winery, with free parking and WiFi.
The price is $113
$113
$130 total
includes taxes & fees
Jan 18 - Jan 19
The Bevin House Bed & Breakfast
The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (83)
9.6/10
Exceptional
(83)
The price is $244
$244
$271 total
includes taxes & fees
Jan 6 - Jan 7
Inn at Middletown
Inn at Middletown
3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (546)
9.0/10
Wonderful
(546)
- Conveniently located in Middletown with an indoor pool and hot tub to unwind.
The price is $181
$181
$228 total
includes taxes & fees
Jan 12 - Jan 13
Red Roof Inn PLUS+ & Suites Guilford
Red Roof Inn PLUS+ & Suites Guilford
2.5 star property
Guilford
7.0 out of 10, Good, (432)
7.0/10
Good
(432)
- Modern comfort near train station with free WiFi and parking in Guilford.
The price is $100
$100
$115 total
includes taxes & fees
Jan 6 - Jan 7
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.
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.
Go beyond your typical stay in Chester
Apartment
Pet friendly
Family friendly
Cottage
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
Norma Terris Theater
If you want to see a show while you're in town, try and grab some tickets at Norma Terris Theater in Chester Center. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy the show and want to see another, Goodspeed Opera House and Ivoryton Playhouse are both not far.
Learn more about Chester
Chester is well-known for its attractions such as Connecticut River and Norma Terris Theater.
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.