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Chester Holiday Rentals

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Holiday Rentals in Chester

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (74)
"Very nice cabins "
United States
Jairo
The price is AU$334
includes taxes & fees
21 Oct - 22 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Rustic Lakeside Cabin at White Gate Farm
10.0 out of 10, Exceptional, (120)
"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
The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AU$257
includes taxes & fees
27 Oct - 28 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
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.
The price is AU$190
includes taxes & fees
20 Oct - 21 Oct
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
10.0 out of 10, Exceptional, (103)
"The Inn and all the staff went so far beyond our expectations. Our daughter and son in law had their wedding celebration on the farm last week. The inn itself is absolutely beautiful. The surroundings are idyllic. We couldn’t have had a better experience staying here. "
United Kingdom
Sarah K.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Freeboard at Soundview · Beach+Ocean+Sunrise
2.0 star property
9.4 out of 10, Exceptional, (6)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
The price is AU$257
includes taxes & fees
22 Oct - 23 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
United States
Catherine
The price is AU$190
includes taxes & fees
20 Oct - 21 Oct
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (38)
"Great place to crash for a night when in town"
United States
Brendan H.
The price is AU$497
includes taxes & fees
22 Oct - 23 Oct
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
10.0 out of 10, Exceptional, (35)
"Lovely stay close to Mohegan Sun- so much nicer than a hotel room!!!"
United States
Mary Anne F.
The price is AU$352
includes taxes & fees
21 Oct - 22 Oct
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Thames River Retreat · CT College+Casinos+USCGA
10.0 out of 10, Exceptional, (17)
"Clean"
United States
PHILLIP
The price is AU$907
includes taxes & fees
26 Oct - 27 Oct
Thames River Retreat · CT College+Casinos+USCGA
Oceanview Villa • Sleeps 22 • Fireplaces • Beach Passes • Pet Friendly
10.0 out of 10, Exceptional, (45)
"Had a family vacation to this property and it couldn’t have gone better. Highly recommend."
United States
jrm99002
Oceanview Villa • Sleeps 22 • Fireplaces • Beach Passes • Pet Friendly
The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun
10.0 out of 10, Exceptional, (5)
"Nice alternative to hotel … after casino show ….would definitely come back !"
United States
Andrew
The price is AU$456
includes taxes & fees
20 Oct - 21 Oct
The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
7.8 out of 10, Good, (12)
"loved the property!"
United States
KADEN T.
The price is AU$308
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Private Apartment in Berlin
2.0 star property
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.
The price is AU$491
includes taxes & fees
20 Oct - 21 Oct
Private Apartment in Berlin
Charming 3-bedroom ranch 1 minute from Mohegan Sun.
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great place! Super clean and easy check in. Plenty of parking."
United States
Daniel W.
The price is AU$804
includes taxes & fees
20 Oct - 21 Oct
Charming 3-bedroom ranch 1 minute from Mohegan Sun.
1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (33)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is AU$277
includes taxes & fees
21 Oct - 22 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
United States
Barb D.
The price is AU$493
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
United States
Julie
The price is AU$405
includes taxes & fees
20 Oct - 21 Oct
Shoreline Oasis
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (33)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Large Charming Historic House close to Beaches
9.8 out of 10, Exceptional, (33)
"Great place and location. There was 8 of us and plenty of space and beds!"
United States
Sandy B.
Large Charming Historic House close to Beaches
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$190 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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 holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theatres while you're in the area.

What are some of the best holiday rentals that Chester has to offer?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This holiday home rental outside of Chester is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.