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Chester Vacation Rentals

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Vacation Rentals in Chester

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is CA $143
CA $221 total
includes taxes & fees
Apr 29 - Apr 30
Postcard Cabins Machimoodus

Regency Inn & Suites

2.0 out of 10, (1)
"Hotel didn’t have out reservation even after we had paid for it - took an hour to check in at midnight - parking lot was full of random activity and people all hours of night and hall ways smelled like weed. Clientele was shady and co within of hotel rooms and surrounding area was dirty, worn out, in need of maintenance and overall place was a dump. Checked out a day early and forfeited a night because place was so disgusting. Expedia needs to remove them from hotel options and do a better job...
The price is CA $105
CA $173 total
includes taxes & fees
Apr 21 - Apr 22
Regency Inn & Suites

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds

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

10.0 out of 10, Exceptional, (33)
"We stayed for 4 nights for the Big East Women’s Basketball Tournament at Mohegan Sun. It was a 3 minute drive from the villa, perfect location. I chose this property because of the great reviews and it didn’t disappoint!The villa was exactly as advertised and exactly what we needed. It was immaculate, beautifully decorated and had everything to make our stay fantastic Taylor, the host, was wonderful to work with and thought of every detail to add to the charm of the villa.The clubhouse has a...
The price is CA $242
CA $475 total
includes taxes & fees
Apr 21 - Apr 22
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

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!

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

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Cozy Coastal Cottage.

10.0 out of 10, Exceptional, (3)
"What a beautiful remodeled house. Cozy and very quiet neighborhood, close to restaurants. "
The price is CA $324
CA $690 total
includes taxes & fees
Apr 21 - Apr 22
Cozy Coastal Cottage.

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (128)
"Very much enjoyed our trip! "
The price is CA $485
CA $940 total
includes taxes & fees
Apr 21 - Apr 22
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

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

9.8 out of 10, Exceptional, (20)
"Had a lovely time at this cozy apartment. Perfect for two. Location and amenities are just as listed. Ample parking and quiet corner unit to rest after touring. Loved the location to Mohegan Sun casino for gaming, Mystic Seaport which has wonderful small shoppes. We also took a drive to Newport RI to visit the mansions. Couldn’t of asked for anything more."
The price is CA $208
CA $400 total
includes taxes & fees
Apr 23 - Apr 24
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

10.0 out of 10, Exceptional, (2)
"Really convenient location breakfast was good. Rooms were clean."
The price is CA $111
CA $156 total
includes taxes & fees
Apr 22 - Apr 23
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

10.0 out of 10, Exceptional, (28)
"It is certainly a cabin in the quiet woods which you would normally find in northern Vermont. We loved everything about it. My Three Sons grew up tent camping in the Yale Forest and this was that, only with a log cabin replacing Eureka tents! We loved sitting around the massive firepit and feeding the flames with plenty of seasoned, dry hardwood, cooking several meals on the coals with pie irons and steak prongs. Just loved it. "
The price is CA $519
CA $993 total
includes taxes & fees
Apr 21 - Apr 22
COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
The price is CA $152
CA $465 total
includes taxes & fees
May 18 - May 19
adorable ranch in beach community

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (14)
"Perfect off season weekend for us with easy access to walks on the beach and lots of relaxing!"
Cozy Westbrook Vacation Rental - Walk to Beach!

Beach House

9.8 out of 10, Exceptional, (51)
"We had such a great experience here! Joseph was so gracious and responsive and went above and beyond to make our stay great. His place is so cute with a mix of whimsical and really convenient touches. Our dog loved the yard, too! The neighborhood is gorgeous, too. We wished we had more time to explore the area and to take advantage of all the house has to offer. "
Beach House

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (89)
"Tuvimos un finde increíble en la casa, súper cómoda y bonita "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

Remodeled Farmhouse in Waterford Near 2 Beaches!

10.0 out of 10, Exceptional, (64)
"This was a perfect location for our family to stay! The home is well appointed and well stocked, and the manager, Tiffany, was responsive and very helpful."
Remodeled Farmhouse in Waterford Near 2 Beaches!

Shoreline Oasis

The price is CA $248
CA $361 total
includes taxes & fees
Apr 21 - Apr 22
Shoreline Oasis

Private Penthouse Paradise

8.0 out of 10, Very good, (2)
"We had previously stayed in a different unit in this complex. We were very happy with the other unit and we understood what the set up was like. We were going to Mohegan Sun and the location is very convenient.I was sent notifications that I needed to verify my identity. I needed to submit a license,a photo and either a 15 fee if I chose to have them hold money on my credit card or a 35 fee if not. I never saw anything in the listing about additional fees so I didn’t care for that. I requested...
The price is CA $202
CA $418 total
includes taxes & fees
Apr 21 - Apr 22
Private Penthouse Paradise

Waterfront House with picture-perfect views from all 3 levels.

9.8 out of 10, Exceptional, (83)
"We had an amazing weekend celebrating my husbands birthday. The house was perfect. The view was priceless. The beach was amazing. It was the first time we were able to travel with our dog, and he had the best time at the beach. We will be returning for another vacation for sure. "
Waterfront House with picture-perfect views from all 3 levels.
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 types of properties in Chester you may be interested in

Mohegan Sun

4.5 star property
9.2 out of 10, Wonderful, (1834)
"We always enjoy our stay here. We ate at Michael Jordan’s steakhouse. Highly recommend this restaurant. Lots of food choices and shops."
The price is CA $262
CA $336 total
includes taxes & fees
May 4 - May 5
Mohegan Sun

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2398)
"Very quiet and safe hotel. The person who checked me in was so amazingly friendly! The breakfast was fine. We asked about a shuttle to Mohegan Sun but it only operates Friday and Saturday. Room was really clean. Housekeeping staff was friendly."
The price is CA $131
CA $151 total
includes taxes & fees
Apr 23 - Apr 24
Hyatt Place Uncasville - Casino Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3.0 star property
9.2 out of 10, Wonderful, (1012)
"All good"
The price is CA $167
CA $193 total
includes taxes & fees
Apr 23 - Apr 24
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
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

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?

Regency Inn & Suites : This vacation home rental near Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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?

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.