A calm river with boats, wooden docks, and buildings along the shore.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Chester vacation rentals

View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (163 reviews)
"Great experience at usual."
United States
Andrea
$192 nightly
The price is $221
Aug 9 - Aug 10
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV

The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
$163 nightly
The price is $184
Jul 12 - Jul 13
Total with taxes and fees
The Tiny Cottage & Mini Farm
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
$228 nightly
The price is $258
Jul 13 - Jul 14
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
1 bedroom, WiFi, bed sheets

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (12 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
$133 nightly
The price is $149
Jul 12 - Jul 13
Total with taxes and fees
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
Exterior

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (37 reviews)
"Nice stay"
United States
WINFOR
$271 nightly
The price is $307
Jul 12 - Jul 13
Total with taxes and fees
Peaceful Oasis Steps from Mohegan Sun
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
$473 nightly
The price is $535
Jul 16 - Jul 17
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Outdoor dining

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (48 reviews)
"Everything was great location, cleanliness, and parking. Enjoyed the stay. Would recommend to anyone looking for a cozy get away!!"
United States
Timothy E.
$300 nightly
The price is $318
Jul 13 - Jul 14
Total with taxes and fees
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
All New 1BR with tons of Charm
Pool

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Norwich
9.6 out of 10, Exceptional, (8 reviews)
"This was a perfect place to stay for any Venues at Mohegan Sun. "
United States
Tracey
$328 nightly
The price is $371
Aug 3 - Aug 4
Total with taxes and fees
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Exterior

Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (13 reviews)
"Close to casino, would recommend"
United States
Joe M.
$565 nightly
The price is $600
Jul 14 - Jul 15
Total with taxes and fees
Winner's Getaway - 2mi to Mohegan Sun
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
$320 nightly
The price is $362
Jul 12 - Jul 13
Total with taxes and fees
Cozy Lakefront Tiny House
A lakeside setting with a row of colorful kayaks and a sailboat docked.

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (156 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
$343 nightly
The price is $388
Jul 26 - Jul 27
Total with taxes and fees
Go Jump in the Lake!
Smart TV

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.6 out of 10, Exceptional, (57 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
$273 nightly
The price is $308
Jul 14 - Jul 15
Total with taxes and fees
Cozy, comfy,quiet &close to casinos
TV

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
All new 1BR apartment with all the features you are looking for
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$310 nightly
The price is $350
Jul 29 - Jul 30
Total with taxes and fees
Lakefront Boho Tiny House
TV

Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$274 nightly
The price is $292
Jul 11 - Jul 12
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
Dining

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
$357 nightly
The price is $390
Jul 31 - Aug 1
Total with taxes and fees
1 Min to I-91 - Newly Renovated Modern 2 BR Home
Spa

Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun

Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun
Norwich
8.8 out of 10, Excellent, (25 reviews)
"Excellent location. Charming place to stay. Would definitely stay here again!"
United States
Ciara W.
$191 nightly
The price is $216
Jul 15 - Jul 16
Total with taxes and fees
Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$297 nightly
The price is $337
Aug 3 - Aug 4
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Interior

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Norwich
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay, host thought of all the little details."
United States
Jessica M.
$352 nightly
The price is $399
Jul 29 - Jul 30
Total with taxes and fees
Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
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

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent
"Very nice people and the place was clean enough"
Erica 1-night trip
Posted less than an hour ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area

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 $149 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.

Explore a world of travel with Expedia

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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This vacation home rental near Chester is located in the city center and has an outdoor pool, a fireplace, 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. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Chester?

Expedia has 3 vacation rentals for your stay in Chester.

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, Chester Creek Marina and Connecticut Valley Railroad State Park Trail 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.