Chester Vacation Rentals

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Our top choices for Chester vacation rentals

The Tiny Cottage on The Ranch

The Tiny Cottage on The Ranch
Oakdale,
10.0 out of 10, Exceptional, (8 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
$133 nightly
The price is $149
May 11 - May 12
Total with taxes and fees
The Tiny Cottage on The Ranch

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, (50 reviews)
"Great location"
United States
Jeff F.
$199 nightly
The price is $225
May 11 - May 12
Total with taxes and fees
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

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, (146 reviews)
"Great stay! "
United States
Tanitra
$158 nightly
The price is $182
Jun 8 - Jun 9
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (51 reviews)
"It was cozy, clean and very close to Mohegan sun! "
United States
Lauren K.
$265 nightly
The price is $300
May 10 - May 11
Total with taxes and fees
Cozy, comfy,quiet &close to casinos

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
$164 nightly
The price is $185
May 14 - May 15
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

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.
$300 nightly
The price is $332
May 11 - May 12
Total with taxes and fees
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

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, (6 reviews)
"great place to stay"
United States
christopher
$286 nightly
The price is $324
May 10 - May 11
Total with taxes and fees
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (48 reviews)
"Small place good for an individual or couple clean and as described."
United States
Anonymous traveler
$295 nightly
The price is $326
May 12 - May 13
Total with taxes and fees
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (32 reviews)
"Host went out their way to make it special for my husband's 70th Birthday! This was our second time staying here. Very clean and accommodating to our needs."
United States
Lori R.
$268 nightly
The price is $304
May 10 - May 11
Total with taxes and fees
Peaceful Oasis Steps from Mohegan Sun

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.
$293 nightly
The price is $330
May 11 - May 12
Total with taxes and fees
Thames River Cottage · Near Casinos - USCGA

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (56 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
$240 nightly
The price is $271
May 18 - May 19
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
$223 nightly
The price is $253
May 11 - May 12
Total with taxes and fees
Cozy Lakefront Tiny House

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)
"Had a wonderful stay last night at Villa Noir. The host was great and everything was as advertised. We would definitely stay here again in the future if the opportunity presents itself."
United States
Dave M.
$275 nightly
The price is $312
May 10 - May 11
Total with taxes and fees
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

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

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
$408 nightly
The price is $461
Jun 1 - Jun 2
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

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.
$530 nightly
The price is $561
May 10 - May 11
Total with taxes and fees
Winner's Getaway - 2mi to Mohegan Sun

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.
$274 nightly
The price is $292
May 10 - May 11
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

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, (22 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
$308 nightly
The price is $349
May 14 - May 15
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$241 nightly
The price is $272
May 11 - May 12
Total with taxes and fees
Lakefront Boho Tiny House

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
$414 nightly
The price is $467
May 12 - May 13
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA

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.
$337 nightly
The price is $381
May 12 - May 13
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Waterford
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 vacation rentals

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

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $182 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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 vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

Cozy, comfy,quiet &close to casinos: This vacation home rental near Chester is equipped with a patio, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Chester?

Expedia has 3 vacation 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 vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.