Chester Holiday Rentals

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Our top choices for Chester holiday rentals

The little Chestnut. A charming historic apartment in Downtown Chester

The little Chestnut. A charming historic apartment in Downtown Chester
Chester Center
10.0 out of 10, Exceptional, (6 reviews)
"A lovely little place! Everything we needed, in a great location."
United States
Michael S.
The price is AU$544
includes taxes & fees
5 Feb - 6 Feb
The little Chestnut. A charming historic apartment in Downtown Chester

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (108 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is AU$246
includes taxes & fees
2 Feb - 3 Feb
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is AU$559
includes taxes & fees
2 Feb - 3 Feb
Beach Cottage, private beach and pass

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
Oakdale,
10.0 out of 10, Exceptional, (3 reviews)
"We were looking for a place to stay while in town for a volleyball tournament. This space worked out perfectly. We will be back! Next time hopefully we’ll have time to enjoy the farm. Thank you!"
United States
Rebecca N.
The price is AU$173
includes taxes & fees
2 Feb - 3 Feb
The Tiny Cottage at Clem & Clyde's

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is AU$528
includes taxes & fees
2 Feb - 3 Feb
Charming 2-bedroom house with WiFi, AC in lovely Waterford

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (16 reviews)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is AU$364
includes taxes & fees
2 Feb - 3 Feb
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is AU$586
includes taxes & fees
4 Feb - 5 Feb
Rogers Lake House (87) · CT College+Beach+USCGA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
New London
8.0 out of 10, Very good, (17 reviews)
"Very cute house with nice extra touches like 2 bottles of water and new toothpaste (perfect because we forgot ours!). "
United States
Christie P.
The price is AU$317
includes taxes & fees
23 Feb - 24 Feb
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

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

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Norwich
10.0 out of 10, Exceptional, (41 reviews)
"We had an amazing stay, everything was perfect! Thank you so much, we would definitely stay again! "
United States
Kerri S.
The price is AU$455
includes taxes & fees
2 Feb - 3 Feb
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.6 out of 10, Exceptional, (8 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is AU$301
includes taxes & fees
2 Feb - 3 Feb
Freeboard at Soundview · Beach+Ocean+Sunrise

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is AU$543
includes taxes & fees
4 Feb - 5 Feb
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (29 reviews)
"Welcoming and felt like home! Extremely clean and would love to stay in this exact location again!!! "
United States
Sandra D.
The price is AU$439
includes taxes & fees
3 Feb - 4 Feb
Peaceful Oasis Steps from Mohegan Sun

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (15 reviews)
"Cottage was perfect. Immaculate, well equipped, beautifully decorated. It had everything we needed! My family and I loved our stay here and will definitely be back."
United States
Nina B.
The price is AU$452
includes taxes & fees
2 Feb - 3 Feb
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (34 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is AU$454
includes taxes & fees
2 Feb - 3 Feb
Walk To Goodspeed Opera House!

Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Charming 3-bedroom ranch 1 minute from Mohegan Sun.
Montville
10.0 out of 10, Exceptional, (16 reviews)
"Great place! Super clean and easy check in. Plenty of parking."
United States
Daniel W.
The price is AU$735
includes taxes & fees
2 Feb - 3 Feb
Charming 3-bedroom ranch 1 minute from Mohegan Sun.

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is AU$475
includes taxes & fees
18 Feb - 19 Feb
#24 *Serenity* A Lakefront Cottage Retreat

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home on the water. Home was very clean and well furnished. Would stay again/recommend."
United States
Christopher O.
The price is AU$854
includes taxes & fees
3 Feb - 4 Feb
Thames River Retreat · CT College+Casinos+USCGA

The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun

The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (8 reviews)
"Had a wonderful stay! The place was spotless, comfortable, and exactly as described. The host was very helpful and accommodating. Would definitely stay again! "
United States
Francesca C.
The price is AU$400
includes taxes & fees
2 Feb - 3 Feb
The Happy Hideaway, steps from Spa and 1 mile to Mohegan Sun

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is AU$547
includes taxes & fees
8 Feb - 9 Feb
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (5 reviews)
"The property was perfect for our trip. Wonderful stay and amazing contact with the hosttess. "
United States
Redebaron 7.
The price is AU$460
includes taxes & fees
2 Feb - 3 Feb
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
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$246 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?

WATERFRONT VIEWS @ OCEAN BEACH GATE: 6 QUEEN 1 SOFA BED: This holiday home rental outside of Chester is located by the ocean, and has an outdoor pool, a furnished patio and air conditioning 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 that you can cook with friends or family.

How many holiday rentals are there in Chester?

Expedia has 3 holiday 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, 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.