Compare Chester Cottage Rentals

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Featured Cottages in Chester

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
$220 nightly
The price is $249 total per night
$249 total
Sep 1 - Sep 2
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

Westbrook CT
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Enchanted Waterfront Cottage

Enchanted Waterfront Cottage

Old Lyme CT
Guests staying at this cottage have access to barbecue grills and a garden.
Charming 1920's no frills cottage in peaceful Old Saybrook

Charming 1920's no frills cottage in peaceful Old Saybrook

Old Saybrook CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Waterfront Getaway! Cozy Cottage in Picture-Perfect Setting, Old Lyme, CT

Waterfront Getaway! Cozy Cottage in Picture-Perfect Setting, Old Lyme, CT

Old Lyme CT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!

3 out of 5
Madison CT
This cottage features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking.
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT
At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views

East Hampton CT
$265 nightly
The price is $300 total per night
$300 total
Sep 7 - Sep 8
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
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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.

Hotel Options in Chester

    Motel 6 New Haven - Branford, CT

    Motel 6 New Haven - Branford, CT

    320 E Main St Branford CT
    $72 nightly
    The price is $83 total per night from Sep 3 to Sep 4
    $83 total
    Sep 3 - Sep 4
    Total with taxes and fees
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $107 nightly
    The price is $123 total per night from Aug 10 to Aug 11
    $123 total
    Aug 10 - Aug 11
    Total with taxes and fees
    Hyatt Place Uncasville - Casino Area

    Hyatt Place Uncasville - Casino Area

    2049 Norwich Montville CT
    $106 nightly
    The price is $122 total per night from Sep 7 to Sep 8
    $122 total
    Sep 7 - Sep 8
    Total with taxes and fees

Cottages

Book a cottage in Chester
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chester. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chester better.

Cottage apartments in Chester range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chester
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chester and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chester cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chester. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chester Cottages essential information

Accommodation
107 Cottages
Lowest Price
$83
Highest Price
$300
Popular accommodation
1-bedroom cottage with Grove Beach 🏖️ access., 2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard, Enchanted Waterfront Cottage, Charming 1920's no frills cottage in peaceful Old Saybrook, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Waterfront Getaway! Cozy Cottage in Picture-Perfect Setting, Old Lyme, CT, 2 Mi to Dtwn: 2-acre Retreat w/ Large Yard!, 4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill, Lakeview Carriage House with Spectacular Sunset Views