Boutique Hotels & Resorts in Chester from AU$124

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Boutique Hotels

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Reception
Spark by Hilton Guilford

Spark by Hilton Guilford

Spark by Hilton Guilford
2.5 star property
Guilford
8.8 out of 10, Excellent, (70)
"Comfortable beds, friendly staff "
United States
Taylor
The price is AU$179
includes taxes & fees
3 Jan - 4 Jan 2026
Spark by Hilton Guilford
Exterior
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area
3.0 star property
Montville
9.2 out of 10, Wonderful, (2595)
"Always a pleasure staying here"
United States
Carrie
The price is AU$168
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Place Uncasville - Casino Area
Exterior
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites
2.5 star property
Berlin
8.6 out of 10, Excellent, (1002)
"great stay."
United States
John
The price is AU$149
includes taxes & fees
2 Jan - 3 Jan 2026
Best Western Plus New England Inn & Suites
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, (1001)
"The young lady at the front desk that welcomed us was absolutely the best."
United States
Corey
The price is AU$125
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn New London - Mystic Area by IHG
Room, 1 Queen Bed, Non Smoking
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area
2.5 star property
Montville
8.8 out of 10, Excellent, (1857)
"We stay here a lot and its clean, affordable and has a nice breakfast. Staff very friendly as well."
United States
Carolan
The price is AU$124
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Uncasville Casino Area
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, (93)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is AU$273
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Free daily buffet breakfast
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North
3.0 star property
North Haven
7.6 out of 10, Good, (1000)
"I would stay there again."
United States
George
The price is AU$153
includes taxes & fees
26 Dec - 27 Dec
Clarion Inn North Haven - New Haven North
Terrace/patio
Hampton Inn Norwich

Hampton Inn Norwich

Hampton Inn Norwich
2.5 star property
Westside Norwich
9.4 out of 10, Exceptional, (1000)
"Nice place to stay"
United States
Scott
The price is AU$174
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Norwich
Standard Studio, 1 King Bed, Non Smoking
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (129)
"Great location. Nice and clean room and property"
United States
Eric
The price is AU$198
includes taxes & fees
5 Jan - 6 Jan 2026
The Niantic Inn
Property grounds
Pier Blue Inn Old Saybrook - Essex

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, (1000)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex
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 Chester Hotel Reviews

Frequently asked questions

What's there to see and do in Chester?
After you've decided where you'd like to stay, figure out some fun things to do on your trip. Attractions and activities to experience around Chester include Connecticut River, Gillette Castle State Park and Goodspeed Opera House. Some other things you might want to enjoy include Norma Terris Theater, Ivoryton Playhouse and East Haddam Historical Society and Museum.
What kind of weather should I plan for when I travel to Chester?
Having a good idea of the weather in Chester is important when planning your trip. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Chester is 1382 mm.
What's the best way to get to my boutique hotel in Chester?
You have a few options for travelling to and around Chester. The nearest major airport is New Haven, CT (HVN-Tweed - New Haven Regional), which is located 23.1 mi (37.2 km) from the heart of the city. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia