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Chester Vacation Rentals

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Vacation Rentals in Chester

Our top choices for Chester vacation rentals

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (54)
"Great stay"
The price is CA $178
CA $260 total
includes taxes & fees
Sep 1 - Sep 2
Postcard Cabins Machimoodus

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (10)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is CA $207
CA $446 total
includes taxes & fees
Aug 29 - Aug 30
Charming houseboat in pleasant New London with AC, WiFi

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (8)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is CA $414
CA $996 total
includes taxes & fees
Aug 31 - Sep 1
Thames River Retreat · CT College+Casinos+USCGA

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is CA $98
CA $258 total
includes taxes & fees
Sep 4 - Sep 5
The Stern at Soundview · Beach+Ocean+Sunrise

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is CA $345
CA $553 total
includes taxes & fees
Sep 3 - Sep 4
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is CA $110
CA $273 total
includes taxes & fees
Sep 3 - Sep 4
The Mast at Soundview · Beach+Ocean+Sunrise

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (5)
The price is CA $124
CA $170 total
includes taxes & fees
Sep 1 - Sep 2
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

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

10.0 out of 10, Exceptional, (140)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is CA $247
CA $359 total
includes taxes & fees
Aug 31 - Sep 1
Shoreline Oasis

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (29)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $160
CA $322 total
includes taxes & fees
Sep 1 - Sep 2
1-bedroom cottage with Grove Beach 🏖️ access.

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (115)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
The price is CA $135
CA $183 total
includes taxes & fees
Aug 31 - Sep 1
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (98)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
The price is CA $1,482
CA $2,671 total
includes taxes & fees
Sep 11 - Sep 12
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (2)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
The price is CA $254
CA $621 total
includes taxes & fees
Sep 9 - Sep 10
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.0 out of 10, Wonderful, (4)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is CA $80
CA $238 total
includes taxes & fees
Sep 3 - Sep 4
Freeboard at Soundview · Beach+Ocean+Sunrise

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (43)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is CA $496
CA $962 total
includes taxes & fees
Sep 1 - Sep 2
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

2.0 star property
9.8 out of 10, Exceptional, (19)
"I’ve stayed here twice and both visits were great. I would definitely recommend this property to anyone looking for a cozy and luxurious space."
The price is CA $292
CA $592 total
includes taxes & fees
Sep 8 - Sep 9
Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

adorable ranch in beach community

9.8 out of 10, Exceptional, (46)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is CA $303
CA $660 total
includes taxes & fees
Sep 22 - Sep 23
adorable ranch in beach community

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (41)
"Perfect for a larger group"
The price is CA $1,555
CA $2,399 total
includes taxes & fees
Sep 1 - Sep 2
Spacious Oceanview Villa (Sleeps 22)

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
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

Find out more about Chester

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $80 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

Thames River Retreat · CT College+Casinos+USCGA: This vacation home rental near Chester is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Chester?

Connecticut River and Connecticut Valley Railroad State Park Trail are a couple of scenic spots to enjoy the outdoors, whereas Norma Terris Theater is one of the cultural attractions. Chester Creek Marina and Gillette Castle State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.