A calm river with boats, wooden docks, and buildings along the shore.

Boutique Hotels & Resorts in Chester from AU$110

  • 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 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

1. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
AU$165
includes taxes & fees
14 Oct - 15 Oct
Quality Inn Old Saybrook - Westbrook
A compact kitchen with wooden walls, a window with a view of greenery, a built-in dishwasher, and a sink.
A cabin with a dining table set for two, a bicycle, and a small porch area.
A wooden cabin room with a bed, a small table, a shelf with books, and a window with a view of trees.
A wooden cabin bathroom with a toilet, a window with a view of trees, and a towel hanging on the wall.

2. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
East Haddam
United States
Morainny
AU$272
includes taxes & fees
30 Sept - 1 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A parking lot with a building in the background.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.

3. Clinton Motel

Clinton Motel
Clinton
United States
Selena
AU$129
includes taxes & fees
27 Sept - 28 Sept
Clinton Motel
A sign for Pier Blue Guesthouse with a logo and name.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.
A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.
A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

4. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
AU$132
includes taxes & fees
12 Oct - 13 Oct
Pier Blue Inn Old Saybrook - Essex
A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.
A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.
A multi-story residential building with blue trim and large windows.
A tranquil park with a gazebo, a pond with a fountain, and a building in the background.

5. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
Old Saybrook
United States
Laurie
AU$110
includes taxes & fees
25 Oct - 26 Oct
Econo Lodge Inn & Suites Old Saybrook Westbrook

6. Motel 6 Old Saybrook, CT

Motel 6 Old Saybrook, CT
Old Saybrook
United States
Carmen
AU$133
includes taxes & fees
27 Sept - 28 Sept
Motel 6 Old Saybrook, CT
A two-story motel with a symmetrical facade, multiple windows, and a parking lot in front.
A bedroom with a dark wooden dresser, a flat-screen TV, a microwave, and a door leading to another room.
A hotel room with a bed, a small table, a chair, a painting on the wall, and a window with a curtain.

7. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
AU$112
includes taxes & fees
7 Oct - 8 Oct
Lamplighter Motel - Clinton, Connecticut
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A spacious room with a large bed, a staircase, and a door leading to another room.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

8. Copper Beech Inn

Copper Beech Inn
Ivoryton
AU$451
includes taxes & fees
28 Sept - 29 Sept
Copper Beech Inn
A large, white, multi-story building with a prominent tower and a flag on top.
A compact living space with a sofa, a chair, a TV, and a small table.
A compact kitchen with white cabinets, a built-in refrigerator, and a sink.
A bedroom with a bed, a television, and a painting of sunflowers.

9. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
United States
Anonymous traveller
AU$356
includes taxes & fees
6 Oct - 7 Oct
Walk To Goodspeed Opera House!
A garden with a fountain, various shrubs, and flower beds.
A kitchen with wooden cabinets, a refrigerator, a coffee maker, and a fruit bowl.
A motel with a two-story structure, a covered parking area, and a landscaped front yard with various plants.
A reception area with a wooden counter, a bulletin board with various notices, a potted plant, and a door leading to another room.

10. Liberty Inn

Liberty Inn
Old Saybrook
United States
Grace
AU$131
includes taxes & fees
5 Oct - 6 Oct
Liberty Inn
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 Essex Steam Train.
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