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Chester Vacation Rentals

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Vacation Rentals in Chester

Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 13 reviews
"Great place. Great host"
Private Guest House w/ Deck + Spectacular Views!
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, 14 reviews
"The Villa was beautiful and immaculately clean. The host, Taylor, was very easy to communicate with. "
The price is CA $240
CA $444 total
includes taxes & fees
Jun 20 - Jun 21
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 113 reviews
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, 21 reviews
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, 10 reviews
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Waterfront Home with a View
9.6 out of 10, Exceptional, 90 reviews
"Peaceful environment, beautiful views, comfort galore. The property lights at night time were a pleasant surprise. Just a few "oh,nooo" comments: laundry was left in the dryer and the washer had some gunk on the inside - the rubber seal when you open it. The dishwasher had spots of mildew in the utensils spot. The wall hook for the curtain in the bedroom broke on the first night - it was barely in the wall. The Keurig was a bonus, 2 touchlanmps in the bedroom with charging ports, large comfy...
The price is CA $232
CA $410 total
includes taxes & fees
Jul 9 - Jul 10
Waterfront Home with a View
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 8 reviews
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Spacious Oceanview Villa (Sleeps 22)
10.0 out of 10, Exceptional, 20 reviews
"My now Wife and I stayed here with our entire wedding party as an alternative from a hotel. This was such an amazing experience, the layout of the house was beautiful and allowed every member to have not only their own sleeping quarters, but private space as well. We were a group of 20 people so options are limited, but this home was a no brainer. Not only was it beautiful, but also functional with a HUGE dining room table and living area on the second floor for the majority of our guests to be...
Spacious Oceanview Villa (Sleeps 22)
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
7.6 out of 10, Good, 4 reviews
"The stairs outside are steep and the apartment is older but it severed the purpose."
The price is CA $177
CA $386 total
includes taxes & fees
Jun 25 - Jun 26
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, 81 reviews
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, 69 reviews
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is CA $617
CA $1,126 total
includes taxes & fees
Jul 18 - Jul 19
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Waterfront! Charming 4BR Cabin on the Niantic River!
9.6 out of 10, Exceptional, 53 reviews
"Enjoyed the uniqueness of the house and location. Note: House and grounds are very nice but not easy to get around if you are elderly and have problems walking.We were in our late sixties/early seventies, not easy getting up to second floor. Low ceilings and doors difficult for 6 ft people. We love the antiques, pantry and great supplies."
Waterfront! Charming 4BR Cabin on the Niantic River!
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, 38 reviews
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
9.8 out of 10, Exceptional, 22 reviews
"The house was great! Perfect amount of space and bathrooms to host my family for my daughter’s wedding. Adorable house with very comfortable beds. There was everything we needed for a beach weekend of fun."
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, 51 reviews
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, 8 reviews
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is CA $246
CA $396 total
includes taxes & fees
Jun 20 - Jun 21
Shalom Cottage with private beach rights.
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, 89 reviews
"Mel and her husband were awesome! Perfect beach home and location was perfect. House was immaculate! I will stay there again. I only needed to use the first floor and did not have to use the stairs. Very close to the beach. Thank you, Mel!"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, 16 reviews
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Don't see what you're looking for?
See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Hyatt Place Uncasville - Casino Area
3.0 star property
9.0 out of 10, Wonderful, 2,080 reviews
"Nice hotel. Friendly staff"
The price is CA $178
CA $204 total
includes taxes & fees
Jun 20 - Jun 21
Hyatt Place Uncasville - Casino Area
Mohegan Sun
4.5 star property
9.2 out of 10, Wonderful, 1,608 reviews
"It was easvand convenient. The spa services were great ! Great stay!!"
The price is CA $259
CA $332 total
includes taxes & fees
Jul 3 - Jul 4
Mohegan Sun
Microtel Inn & Suites by Wyndham Uncasville Casino Area
2.5 star property
8.8 out of 10, Excellent, 1,558 reviews
"Great place to stay. Close to restaurants as well"
The price is CA $114
CA $131 total
includes taxes & fees
Jun 20 - Jun 21
Microtel Inn & Suites by Wyndham Uncasville Casino 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.

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 $177 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?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This vacation home near Chester is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a spa tub.

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. While here, Chester Creek Marina and Cockaponset State Forest 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.

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