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Aug 15 - Aug 17
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Cottages in Chester

1-bedroom cottage with Grove Beach 🏖️ access.
Enjoy a casual outdoor space with a front porch, potted plant, and Adirondack chairs.

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
$229 nightly
The price is $259
Sep 1 - Sep 2
Total includes taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Stunning historical building with a central tower and traditional pitched roof.

Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach

9.2 out of 10, Wonderful, (7)
"It was nice and relaxing...walking, swimming, biking, kayaking and beaching. The house was super cool...150 years old! Nice old fashioned laid back beach vacation! Mary the host was wonderful!"
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Sweet Cottage in Beach Community
Stroll along the garden pathway to a charming home with a cozy porch and lush surroundings.

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (10)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
Beachside Branford- walk to Beach, Grill
Exterior

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
Go Jump in the Lake!
Situated in a wooded area, this cozy shed features a simple design with a front door and two windows.

Go Jump in the Lake!

10.0 out of 10, Exceptional, (143)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Direct waterfront renovated cottage.
Enjoy outdoor dining or relaxation on the covered patio with comfortable seating and tables.

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (76)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Traditional cottage with a front porch and garden, offering a peaceful retreat.

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (16)
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct
Exterior

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct

Charming 4-bedroom beach front cottage in beautiful Old Lyme Ct
DIRECT WATERFRONT PRIVATE BEACH
Relax on the patio with a clear view of the water, surrounded by a low wall for added seclusion.

DIRECT WATERFRONT PRIVATE BEACH

9.4 out of 10, Exceptional, (23)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH
Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
Exterior

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT

Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
Luxury Tiny Home In Niantic
Situated in a forested area, this cabin features a cozy front porch with a seating area and a stone wall.

Luxury Tiny Home In Niantic

10.0 out of 10, Exceptional, (4)
"This property is perfect for 2-3 guests and located within short distance to town. The house is well built and very clean. Five Stars"
Luxury Tiny Home In Niantic
Guilford Carriage House at Granite Lodge!
Set amidst leafless trees, this charming barn-style building offers a serene country retreat.

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Stylish single-story home with a gabled roof and chimney, featuring a front entrance and wooden deck.

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

9.0 out of 10, Wonderful, (2)
"Perfect little beachfront cottage right on the water ...a few steps across your own beach. We had a very relaxing, comfortable visit."
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Surrounded by lush greenery, this charming house boasts a cozy balcony overlooking the forest.

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

10.0 out of 10, Exceptional, (3)
"Lovely location and host."
$472 nightly
The price is $534
Aug 10 - Aug 11
Total includes taxes and fees
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Enjoy ocean views and outdoor activities in a serene backyard with a covered grill area and deck.

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

9.8 out of 10, Exceptional, (72)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Historic cottage in Deep River, CT
Charming cottage with a traditional design, surrounded by a well-maintained garden and a peaceful setting.

Historic cottage in Deep River, CT

10.0 out of 10, Exceptional, (1)
"Wonderful stay. Charming and perfect. "
$325 nightly
The price is $368
Sep 2 - Sep 3
Total includes taxes and fees
Historic cottage in Deep River, CT
Beach Cottage
Residential neighborhood with a variety of houses, well-manicured lawns, and gardens.

Beach Cottage

10.0 out of 10, Exceptional, (8)
"Great location! Easy communication. "
$486 nightly
The price is $550
Sep 7 - Sep 8
Total includes taxes and fees
Beach Cottage
Adorable Cottage with Cottage porch, walk to water & town
Relax on the sheltered front porch, perfect for unwinding.

Adorable Cottage with Cottage porch, walk to water & town

8.8 out of 10, Excellent, (6)
"Very nice and comfortable property "
Adorable Cottage with Cottage porch, walk to water & town
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Traditional two-story house with a central entrance and shutters, set amidst a well-manicured lawn.

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (3)
"A perfect stay - John and his family were truly wonderful. The house is attached to thier main house, but also very private and secure. We were in town for a wedding weekend and this was the perfect spot for us - truly a beatuiful property! John was helpful in telling us about all of the local spot and supplying us with everything we needed. His wife even welcomed us with a cheese board and wine! Thanks John and family - we had a great time!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Relax with a beautiful lake view
Enjoy a peaceful stay in this charming single-story home with a balcony overlooking a serene grassy yard.

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (20)
"Great location"
Relax with a beautiful lake view
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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Top Chester Hotel Reviews

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

10/10 Excellent
"It didn’t start out great but I called the hotel staff and they changed out room and made it right. Definitely a game changer for our stay. Thank you "
Jane 1-night trip
Posted 14 hours ago
Hyatt Place Uncasville - Casino Area