Chester Holiday Rentals

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Our top choices for Chester holiday rentals

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, (91)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is AU$275
includes taxes & fees
15 Jan - 16 Jan 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is AU$185
includes taxes & fees
17 Dec - 18 Dec
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Rustic Lakeside Cabin at White Gate Farm

Rustic Lakeside Cabin at White Gate Farm
East Lyme
10.0 out of 10, Exceptional, (124)
"5-star lake view. Amazing stay. we absolutely enjoyed visiting this farm every year. "
United States
Mariya S.
Rustic Lakeside Cabin at White Gate Farm

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
New London
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$185
includes taxes & fees
17 Dec - 18 Dec
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (17)
"We stayed at the Thames River House after our wedding with friends and it was the perfect spot. The home was beautiful, very clean, and had everything we needed for a relaxing and memorable stay. Couldn’t have asked for a better experience!"
United States
Brandon W.
The price is AU$869
includes taxes & fees
17 Dec - 18 Dec
Thames River Retreat · CT College+Casinos+USCGA

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

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
10.0 out of 10, Exceptional, (41)
"Everything was easy .. comfortable host was very helpful and communicable. "
United States
Cathleen S.
The price is AU$383
includes taxes & fees
21 Dec - 22 Dec
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

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, (16)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
The price is AU$288
includes taxes & fees
17 Dec - 18 Dec
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, (40)
"Great place to crash for a night when in town"
United States
Brendan H.
The price is AU$482
includes taxes & fees
17 Dec - 18 Dec
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun
2.0 star property
Norwich
10.0 out of 10, Exceptional, (24)
"Absolutely beautiful and calm space! "
United States
Ayana
The price is AU$591
includes taxes & fees
21 Dec - 22 Dec
Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

Cozy Coastal Cottage New London

Cozy Coastal Cottage New London
New London
9.4 out of 10, Exceptional, (10)
"It was the perfect little place for a night away from the kids. "
United States
Tonya B.
The price is AU$671
includes taxes & fees
17 Dec - 18 Dec
Cozy Coastal Cottage New London

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is AU$283
includes taxes & fees
18 Dec - 19 Dec
1-bedroom cottage with Grove Beach 🏖️ access.

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

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
Waterford
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is AU$444
includes taxes & fees
17 Dec - 18 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Private Penthouse Paradise

Private Penthouse Paradise
Norwich
7.6 out of 10, Good, (4)
"I like the quiet and peaceful setting the place was a litte smaller than it sounded, the people were friendly and kind if i was to do this again i would perfer bigger accommodations . I enjoyed the pool & hottub we had a very good stay"
United States
Edward
The price is AU$423
includes taxes & fees
17 Dec - 18 Dec
Private Penthouse Paradise

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is AU$394
includes taxes & fees
17 Dec - 18 Dec
Shoreline Oasis

Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is AU$1,415
includes taxes & fees
17 Dec - 18 Dec
Conference Room Rental no sleeping arrangements

Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Charming 3-bedroom ranch 1 minute from Mohegan Sun.
2.0 star property
Montville
10.0 out of 10, Exceptional, (14)
"Great place! Super clean and easy check in. Plenty of parking."
United States
Daniel W.
The price is AU$786
includes taxes & fees
17 Dec - 18 Dec
Charming 3-bedroom ranch 1 minute from Mohegan Sun.

Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
Branford
10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation!! The house was perfect, check in couldn’t have easier and the views couldn’t have been better. A perfect summer getaway."
United States
Mike S.
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
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$477
includes taxes & fees
11 Jan - 12 Jan 2026
Private Apartment in Berlin

Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views

Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views
New London
10.0 out of 10, Exceptional, (45)
"Comfortable and very spacious house - was great for our family reunion. Close to lots of fun things and nice views of water. "
United States
zachary b.
The price is AU$1,405
includes taxes & fees
17 Dec - 18 Dec
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (28)
"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$461
includes taxes & fees
17 Dec - 18 Dec
Peaceful Oasis Steps from Mohegan Sun
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$185 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?

Thames River Retreat · CT College+Casinos+USCGA: This holiday home rental outside of Chester is located on a river, and has a fireplace, a balcony and a BBQ 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.