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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 140 Cottages in Chester with updated reviews, rates, and availability.

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
Beach nearby, sun loungers

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Smart TV

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AED 323
AED 635 total
includes taxes & fees
24 Mar - 25 Mar
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

10.0 out of 10, Exceptional, (2)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"We booked last minute as we decided to join family staying in Old Lyme. This cottage was just perfect for our needs. My husband and I along with our 19 year old stayed here. Clean, newly remodeled and amenities to meet our needs for a 3 day beach retreat. Simple, but practical. Close to beach and a/c was a treat during the heat wave! ⭐️⭐️⭐️⭐️⭐️"
Charming Old Lyme Cottage, Steps to Private Beach!
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Dining

Beachside Branford- walk t0 Beach, Grill, Fire Pit

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Private Guest House w/ Deck + Spectacular Views!
Property grounds

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"Meetings with friends who were staying at Mohegan Sun which was 20 minutes away. Pretty views, comfortable property. Would definitely return "
Private Guest House w/ Deck + Spectacular Views!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Classic Cottage in Best Private Community in Old Lyme CT.
Beach nearby, sun loungers, beach towels

Classic Cottage in Best Private Community in Old Lyme CT.

10.0 out of 10, Exceptional, (27)
"Great little house very close to the sound. Met our needs perfectly!"
Classic Cottage in Best Private Community in Old Lyme CT.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Guilford Carriage House at Granite Lodge!
TV

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (9)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (3)
"Excellent experience. Great host. Clean, inviting property near beach. Cozy home. Good value. Will stay again. Thank you. "
The price is AED 1,098
AED 2,052 total
includes taxes & fees
25 Mar - 26 Mar
Beach Cottage
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach
Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach

Direct waterfront 3-bedroom cottage in Old Lyme, Hawks Nest Beach
Charming Old Saybrook Cottage < 1 Mi to Beach
Fridge, microwave, stovetop, dishwasher

Charming Old Saybrook Cottage < 1 Mi to Beach

10.0 out of 10, Exceptional, (27)
"Was close to the beach and town. "
Charming Old Saybrook Cottage < 1 Mi to Beach
Relax with a beautiful lake view
Outdoor dining

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
TV, stereo

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
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, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Beach access Cozy Cottage
Sun loungers, beach towels

Beach access Cozy Cottage

9.8 out of 10, Exceptional, (6)
"Very clean and adorable place providing all one needs for peace and respite. I would return again."
Beach access Cozy Cottage
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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Other property types in Chester

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
The price is AED 496
AED 570 total
includes taxes & fees
3 Apr - 4 Apr
Postcard Cabins Machimoodus
Regency Inn & Suites
1 bedroom, iron/ironing board, WiFi, bed sheets

Regency Inn & Suites

The price is AED 279
AED 458 total
includes taxes & fees
31 Mar - 1 Apr
Regency Inn & Suites
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Indoor pool, a heated pool

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (32)
"Everything was absolutely perfect! The place is adorable inside and out and so close to Mohegan. It was ideal for a mother/daughter trip to see Billy Joel. Thank you! "
The price is AED 643
AED 1,259 total
includes taxes & fees
23 Mar - 24 Mar
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
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.

Frequently asked questions

How much do cottages in Chester cost?
You can expect to pay between AED 323 and AED 1,098 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 140 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.
How can I find cheap cottages in Chester?
With Expedia’s filter tool, scoring cheap cottages in Chester has never been simpler. To view properties that’ll make your bank balance smile, refine your search by amenities, budget and star rating.