Holiday Rentals in Chester

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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, (136 reviews)
"Our favorite place to visit ♥️"
United States
Teresa
The price is €174
includes taxes & fees
30 Apr - 1 May
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is €362
includes taxes & fees
22 Apr - 23 Apr
Entire Vacation Home in Waterford Connecticut

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 €313
includes taxes & fees
17 Apr - 18 Apr
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"Only stayed for 1 night but the house was clean and had what our group needed. Beautiful location. "
United States
Alexander L.
The price is €699
includes taxes & fees
20 Apr - 21 Apr
Thames River Retreat · CT College+Casinos+USCGA

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is €798
includes taxes & fees
4 May - 5 May
Tranquil Farmhouse Retreat

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, (42 reviews)
"My girlfriend and I had a wonderful time here it was GREAT.!"
United States
Kareem
The price is €274
includes taxes & fees
19 Apr - 20 Apr
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €221
includes taxes & fees
20 Apr - 21 Apr
The Stern at Soundview · Beach+Ocean+Sunrise

Winner's Getaway - 2mi to Mohegan Sun

Winner's Getaway - 2mi to Mohegan Sun
Westside Norwich
10.0 out of 10, Exceptional, (12 reviews)
"Close to casino, would recommend"
United States
Joe M.
The price is €456
includes taxes & fees
4 May - 5 May
Winner's Getaway - 2mi to Mohegan Sun

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is €411
includes taxes & fees
14 May - 15 May
Beach Cottage, private beach and pass

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (29 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is €221
includes taxes & fees
22 Apr - 23 Apr
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

East Haddam Lake View Rental

East Haddam Lake View Rental
East Haddam
The price is €379
includes taxes & fees
19 Apr - 20 Apr
East Haddam Lake View Rental

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is €373
includes taxes & fees
20 Apr - 21 Apr
Rogers Lake House (87) · CT College+Beach+USCGA

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (26 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is €830
includes taxes & fees
26 Apr - 27 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Norwich
10.0 out of 10, Exceptional, (14 reviews)
"We had a wonderful stay, host thought of all the little details."
United States
Jessica M.
The price is €268
includes taxes & fees
23 Apr - 24 Apr
Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (2 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is €288
includes taxes & fees
20 Apr - 21 Apr
Thames River Cottage · Near Casinos - USCGA

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (35 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 €204
includes taxes & fees
21 Apr - 22 Apr
Walk To Goodspeed Opera House!

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

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (28 reviews)
"We loved our stay! Beautifully decorated, clean and spacious! We will definitely be back!"
United States
Theresa C.
The price is €363
includes taxes & fees
27 Apr - 28 Apr
Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is €364
includes taxes & fees
21 Apr - 22 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic

#29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is €374
includes taxes & fees
19 Apr - 20 Apr
#29 - Modern 5 Bedroom/2 Bath

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (127 reviews)
"Great property!"
United States
Matthew B.
The price is €482
includes taxes & fees
19 Apr - 20 Apr
Coastal New England Waterfront Home, Harkness Park, 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, apart-hotels, 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 favorite 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 depends 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 €122 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 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?

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA: This holiday home rental outside of Chester is located next to a golf course, and offers a garden, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.