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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

Cottages in Chester

1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

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"
The price is AED 536
AED 1,009 total
includes taxes & fees
19 Aug - 20 Aug
1-bedroom cottage with Grove Beach 🏖️ access.
Now has TV + linens - Relaxing 4-bedroom cottage in Westbrook, CT at West Beach
Exterior

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
Fridge, microwave, oven, stovetop

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
Dining

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!

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.
TV, books

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
Property grounds

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
Beach

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
Private beach

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
Smart TV, fireplace

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
Exterior

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!
Interior

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
Interior

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
Property grounds

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

10.0 out of 10, Exceptional, (3)
"Lovely location and host."
The price is AED 1,157
AED 1,962 total
includes taxes & fees
10 Aug - 11 Aug
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
On the beach, sun loungers, beach towels

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
Property grounds

Historic cottage in Deep River, CT

10.0 out of 10, Exceptional, (1)
"Wonderful stay. Charming and perfect. "
The price is AED 713
AED 1,350 total
includes taxes & fees
2 Sep - 3 Sep
Historic cottage in Deep River, CT
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (8)
"Great location! Easy communication. "
The price is AED 1,051
AED 2,019 total
includes taxes & fees
7 Sep - 8 Sep
Beach Cottage
Adorable Cottage with Cottage porch, walk to water & town
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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
Outdoor dining

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 12 hours ago
Hyatt Place Uncasville - Casino Area

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between AED 536 and AED 1,157 per night for cottages in Chester. No matter your budget, an epic stay is only a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chester?
Enjoy reconnecting with nature in one of the 143 cottages located in Chester. To help you find your ideal place, use our handy filter tool to search for must-have amenities.
Why book your cottage in Chester with Expedia?
We think that a vacay should be simple, so if you're after cottages in Chester at a great price, Expedia delivers. Stick to the budget and go for a wallet-friendly option far from the hustle and bustle, or book a luxury cottage to spoil your favorite people.