Mystic, Stonington, Connecticut, United States - October 26, 2018: Panoramic view of old historic homes by the Mystic River during a vibrant sunrise.

Chester Holiday Rentals

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Our top choices for Chester holiday rentals

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is AU$455
includes taxes & fees
22 June - 23 June
Cozy Lakefront Tiny House

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is AU$448
includes taxes & fees
30 June - 1 July
Private Apartment in Berlin

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, (156 reviews)
"Great stay! "
United States
Tanitra
The price is AU$299
includes taxes & fees
22 June - 23 June
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (45 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is AU$355
includes taxes & fees
28 June - 29 June
1-bedroom cottage with Grove Beach 🏖️ access.

The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is AU$214
includes taxes & fees
21 June - 22 June
The Tiny Cottage & Mini Farm

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (35 reviews)
"Nice stay"
United States
WINFOR
The price is AU$432
includes taxes & fees
21 June - 22 June
Peaceful Oasis Steps from Mohegan Sun

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
9.8 out of 10, Exceptional, (53 reviews)
"Great location"
United States
Jeff F.
The price is AU$377
includes taxes & fees
30 June - 1 July
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (56 reviews)
"Clean home. Couldn’t be easier to get to Mohegan Sun! Very convenient."
United States
Angela
The price is AU$377
includes taxes & fees
24 June - 25 June
Cozy, comfy,quiet &close to casinos

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is AU$582
includes taxes & fees
29 June - 30 June
#24 *Serenity* A Lakefront Cottage Retreat

1 Min to I-91 - Newly Renovated Modern 2 BR Home

1 Min to I-91 - Newly Renovated Modern 2 BR Home
Berlin
The price is AU$441
includes taxes & fees
24 June - 25 June
1 Min to I-91 - Newly Renovated Modern 2 BR Home

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$414
includes taxes & fees
22 June - 23 June
Once the old Schools house now a newly furnished Apartment

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (17 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$578
includes taxes & fees
7 July - 8 July
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

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, (43 reviews)
"My girlfriend and I had a wonderful time here it was GREAT.!"
United States
Kareem
The price is AU$451
includes taxes & fees
25 June - 26 June
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 AU$444
includes taxes & fees
21 June - 22 June
The Stern at Soundview · Beach+Ocean+Sunrise

Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun

Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun
Norwich
9.0 out of 10, Wonderful, (20 reviews)
"We haf a great stay woukd love to do again sonetime."
United States
Bethany R.
The price is AU$307
includes taxes & fees
1 July - 2 July
Luxe Condo in Norwich Less Than 3 Minutes From Mohegan Sun

Fabulous Tiny House Surrounded by Forest in Norwich, Connecticut

Fabulous Tiny House Surrounded by Forest in Norwich, Connecticut
Norwich
The price is AU$274
includes taxes & fees
24 June - 25 June
Fabulous Tiny House Surrounded by Forest in Norwich, Connecticut

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is AU$417
includes taxes & fees
21 June - 22 June
All new 1BR apartment with all the features you are looking for

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Norwich
9.6 out of 10, Exceptional, (8 reviews)
"This was a perfect place to stay for any Venues at Mohegan Sun. "
United States
Tracey
The price is AU$450
includes taxes & fees
22 June - 23 June
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Easy Beach Access! Classic New London Charmer

Easy Beach Access! Classic New London Charmer
3.5 star property
New London
The price is AU$552
includes taxes & fees
6 July - 7 July
Easy Beach Access! Classic New London Charmer

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 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$453
includes taxes & fees
18 June - 19 June
Walk To Goodspeed Opera House!
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$214 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?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: This holiday home rental outside of Chester is located in the city centre, and has an outdoor pool, a fireplace 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. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

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.