Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Charming 2-bedroom townhome

Charming 2-bedroom townhome

2 out of 5
Berlin
The price is AU$264 per night from 24 Nov to 25 Nov
AU$264
includes taxes & fees
24 Nov - 25 Nov
With a stay at this vacation home in Berlin, you'll be within a 10-minute drive of Checkered Flag Raceway and Lincoln Technical Institute.
Charming 2-bedroom townhome
Waterfront Beach House

Waterfront Beach House

Clinton
Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store ...
Waterfront Beach House
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Branford
Located in Branford, this vacation home is by the ocean, within a 10-minute drive of Polished and Stony Creek Brewery.
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Clinton
When you stay at this vacation home in Clinton, you'll be near the beach and 11 minutes by foot from Clinton Town Beach.
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Oceanfront Beach House lay in bed and hear the waves, boats , birds

Waterford
Located in Waterford, this vacation home is on the beach, a 2-minute walk from Pleasure Beach and within a 5-minute drive of Harkness Memorial State Park.
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Historic Essex Home w/ Large Yard Near Downtown!

Historic Essex Home w/ Large Yard Near Downtown!

Essex
With a stay at this vacation home in Essex, you'll be a 4-minute walk from Connecticut Valley Railroad State Park and 6 minutes by foot from Essex Steam ...
Historic Essex Home w/ Large Yard Near Downtown!
Beach House

Beach House

East Lyme
Located in Niantic, this vacation home is by the sea, a 3-minute drive from Attawan Beach and 6 minutes from McCook Point Beach.
Beach House
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

Old Saybrook
Located in Old Saybrook, this vacation home is by the ocean, within a 5-minute drive of Harvey's Beach and General William Hart House.
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Ocean Beach Park Lawrence  M.Hosp MitchellCollege Coast Guard Academy CT College

Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

New London
Located in New London, this vacation home is by the sea, within a 5-minute walk of Ocean Beach Park and Waterford Beach Park.
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College
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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.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
307 Holiday Homes
Lowest Price
AU$124
Highest Price
AU$355
Popular accommodation
Charming 2-bedroom townhome , Waterfront Beach House, Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub , Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Oceanfront Beach House lay in bed and hear the waves, boats , birds, Historic Essex Home w/ Large Yard Near Downtown!, Beach House, OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW, Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Top trending hotels in Chester

Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
The price is AU$355 per night from 25 Nov to 26 Nov
AU$355
includes taxes & fees
25 Nov - 26 Nov
Located in Montville, Mohegan Sun is connected to the convention center, within a 15-minute walk of Mohegan Sun Arena and Mohegan Sun Casino.
Mohegan Sun
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 25 Nov to 26 Nov
AU$186
includes taxes & fees
25 Nov - 26 Nov
When you stay at Hyatt Place Uncasville - Casino Area in Montville, you'll be near the airport, within a 5-minute drive of Mohegan Sun Casino and Mohegan Sun ...
Hyatt Place Uncasville - Casino Area
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is AU$124 per night from 2 Dec to 3 Dec
AU$124
includes taxes & fees
2 Dec - 3 Dec
Located in Branford, Motel 6 New Haven - Branford, CT is within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Motel 6 New Haven - Branford, CT
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Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St, Meriden, CT
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 24 Nov to 25 Nov
AU$147
includes taxes & fees
24 Nov - 25 Nov
A stay at Red Roof Inn Meriden places you in the heart of Meriden, within a 5-minute drive of Saint Johns Field and Black Pond State Wildlife Area.
Red Roof Inn Meriden
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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.

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^Subject to availability and chosen travel dates.