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Chester Vacation Rentals

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Vacation Rentals in Chester

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.0 star property
East Haddam
9.6 out of 10, Exceptional, (79)
"Very nice cabins "
United States
Jairo
$189 nightly
The price is $217
Nov 11 - Nov 12
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Rustic Lakeside Cabin at White Gate Farm

East Lyme
10.0 out of 10, Exceptional, (123)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
United States
James N.
Rustic Lakeside Cabin at White Gate Farm

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

New London
10.0 out of 10, Exceptional, (7)
"William was great. Room was perfectly clean. Fresh towels, water bottles, croissants, and coffee everyday was a really nice touch. "
United States
Jake L.
$108 nightly
The price is $121
Nov 9 - Nov 10
Total with taxes and fees
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

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

East Lyme
10.0 out of 10, Exceptional, (106)
"We had such an amazing time here and are planning to return for our next family vacation! The house was clean and spacious and the communication was phenomenal. Everyone we interacted with at the farm was kind, caring, and helpful. There is so much to do at the farm and in the surrounding area. We could not recommend this place more! Best vacation ever!"
United States
Adrienne N.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

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

New London
9.6 out of 10, Exceptional, (12)
"Bill was an amazing host, he went above and beyond to make our stay as enjoyable as humanly possible I'd highly recommend this place to anyone who is looking to visit the Mystic and New London Connecticut area l."
United States
CJ
$108 nightly
The price is $121
Nov 9 - Nov 10
Total with taxes and fees
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
$192 nightly
The price is $218
Nov 11 - Nov 12
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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

Norwich
10.0 out of 10, Exceptional, (38)
"Great place to crash for a night when in town"
United States
Brendan H.
$282 nightly
The price is $319
Nov 9 - Nov 10
Total with taxes and fees
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
$230 nightly
The price is $261
Nov 8 - Nov 9
Total with taxes and fees
Shoreline Oasis

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Norwich
10.0 out of 10, Exceptional, (37)
"a little smaller than the pictures make it seem, but it's a cute and cozy little place. "
United States
Andrew P.
$208 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Thames River Retreat · CT College+Casinos+USCGA

Waterford
10.0 out of 10, Exceptional, (17)
"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."
United States
Wendy H.
$541 nightly
The price is $611
Nov 9 - Nov 10
Total with taxes and fees
Thames River Retreat · CT College+Casinos+USCGA

The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun

Norwich
10.0 out of 10, Exceptional, (6)
"Nice alternative to hotel … after casino show ….would definitely come back !"
United States
Andrew
$272 nightly
The price is $308
Nov 16 - Nov 17
Total with taxes and fees
The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$279 nightly
The price is $316
Nov 9 - Nov 10
Total with taxes and fees
Private Apartment in Berlin

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

New London
8.0 out of 10, Very Good, (13)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
$174 nightly
The price is $197
Nov 12 - Nov 13
Total with taxes and fees
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Waterfront Cottage in Branford

branford
10.0 out of 10, Exceptional, (97)
"Host was wonderful to work with. House is amazing. Very spacious, beds were 5 Star hotel worthy!The location and view were spectacular. This was a perfect location and checked off ALL the boxes. "
United States
Kelly C.
Waterfront Cottage in Branford

Oceanview Villa • Sleeps 22 • Fireplaces • Beach Passes • Pet Friendly

New London
10.0 out of 10, Exceptional, (45)
"Thank you for a lovely stay."
United States
Marie G.
$865 nightly
The price is $979
Nov 11 - Nov 12
Total with taxes and fees
Oceanview Villa • Sleeps 22 • Fireplaces • Beach Passes • Pet Friendly

Peaceful Oasis Steps from Mohegan Sun

Norwich
10.0 out of 10, Exceptional, (28)
"Enjoyed the stay. Great location. Host was excellent. "
United States
William H.
$270 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Peaceful Oasis Steps from Mohegan Sun

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (35)
"This place is exactly as described. Was absolutely perfect, cozy, and comfortable. Thanks Kevin!"
United States
johanna s.
$280 nightly
The price is $317
Nov 8 - Nov 9
Total with taxes and fees
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

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

Branford
10.0 out of 10, Exceptional, (71)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cozy dog friendly updated house in quiet village adjacent to park

Northford
10.0 out of 10, Exceptional, (43)
"Very nice stay! Yard is beautiful!"
United States
Marilee P.
Cozy dog friendly updated house in quiet village adjacent to park

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
$1,045 nightly
The price is $1,182
Nov 27 - Nov 28
Total with taxes and fees
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This vacation home rental near Chester is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Chester?

Cultural attractions include Norma Terris Theater, whereas Connecticut River is a spot to enjoy nature. While here, Connecticut Valley Railroad State Park Trail and Chester Creek Marina are other places worth a visit.

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.