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

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 stay! "
United States
Tanitra
The price is AED 529
AED 777 total
includes taxes & fees
5 Aug - 6 Aug
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.
The price is AED 643
AED 927 total
includes taxes & fees
12 Jul - 13 Jul
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.
The price is AED 526
AED 946 total
includes taxes & fees
13 Jul - 14 Jul
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.
The price is AED 413
AED 549 total
includes taxes & fees
8 Jul - 9 Jul
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
The price is AED 595
AED 1,126 total
includes taxes & fees
8 Jul - 9 Jul
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.
The price is AED 611
AED 1,856 total
includes taxes & fees
8 Jul - 9 Jul
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.
The price is AED 608
AED 1,353 total
includes taxes & fees
13 Jul - 14 Jul
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)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,071 total
includes taxes & fees
8 Jul - 9 Jul
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
The price is AED 602
AED 1,184 total
includes taxes & fees
8 Jul - 9 Jul
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, (12 reviews)
"Close to casino, would recommend"
United States
Joe M.
The price is AED 749
AED 1,978 total
includes taxes & fees
8 Jul - 9 Jul
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)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is AED 586
AED 1,104 total
includes taxes & fees
8 Jul - 9 Jul
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.
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.
The price is AED 526
AED 1,148 total
includes taxes & fees
14 Jul - 15 Jul
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.
The price is AED 433
AED 1,071 total
includes taxes & fees
8 Jul - 9 Jul
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.
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.
The price is AED 433
AED 1,071 total
includes taxes & fees
11 Jul - 12 Jul
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
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.
The price is AED 539
AED 793 total
includes taxes & fees
15 Jul - 16 Jul
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.
The price is AED 632
AED 1,263 total
includes taxes & fees
3 Aug - 4 Aug
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.
The price is AED 657
AED 1,254 total
includes taxes & fees
9 Jul - 10 Jul
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

Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

10/10 Excellent
"Staff great breakfast better than continental more like a buffet. Room was nice. Close to freeway"
donna 2-night trip
Posted 11 hours ago
Regency Inn & Suites New London, Mystic

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.