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.
The price is CA $154
CA $204 total
includes taxes & fees
May 11 - May 12
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.
The price is CA $166
CA $347 total
includes taxes & fees
May 11 - May 12
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
The price is CA $190
CA $281 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $183
CA $413 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $116
CA $253 total
includes taxes & fees
May 14 - May 15
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.
The price is CA $173
CA $443 total
includes taxes & fees
May 12 - May 13
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
The price is CA $178
CA $441 total
includes taxes & fees
May 10 - May 11
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 traveller
The price is CA $163
CA $431 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $221
CA $418 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $171
CA $457 total
includes taxes & fees
May 11 - May 12
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.
The price is CA $154
CA $372 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $167
CA $345 total
includes taxes & fees
May 11 - May 12
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.
The price is CA $216
CA $429 total
includes taxes & fees
May 10 - May 11
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
The price is CA $243
CA $637 total
includes taxes & fees
Jun 2 - Jun 3
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.
The price is CA $279
CA $763 total
includes taxes & fees
May 10 - May 11
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.
The price is CA $161
CA $400 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $234
CA $475 total
includes taxes & fees
May 14 - May 15
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.
The price is CA $188
CA $375 total
includes taxes & fees
May 11 - May 12
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
The price is CA $187
CA $636 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $219
CA $521 total
includes taxes & fees
May 12 - May 13
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.