A calm river with boats, wooden docks, and buildings along the shore.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chester vacation rentals

View from property

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (182 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
$219 nightly
The price is $252
Aug 26 - Aug 27
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

2. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
$216 nightly
The price is $244
Sep 22 - Sep 23
Total with taxes and fees
Walk To Goodspeed Opera House!
Room

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
$197 nightly
The price is $222
Sep 15 - Sep 16
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Living area

4. 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, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
$228 nightly
The price is $258
Sep 1 - Sep 2
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Private kitchen

5. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$291 nightly
The price is $329
Sep 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
Beach

6. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
$324 nightly
The price is $366
Sep 3 - Sep 4
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Living area

7. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
$142 nightly
The price is $160
Aug 26 - Aug 27
Total with taxes and fees
The Tiny Cottage & Mini Farm
Beach

8. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
$330 nightly
The price is $372
Sep 22 - Sep 23
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Dining

9. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
$263 nightly
The price is $298
Aug 26 - Aug 27
Total with taxes and fees
2BR Apartment Near Wesleyan 102
Exterior

10. 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.
$262 nightly
The price is $296
Sep 22 - Sep 23
Total with taxes and fees
Cozy Lakefront Tiny House
Property grounds

11. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$269 nightly
The price is $304
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
Room

12. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$248 nightly
The price is $280
Sep 22 - Sep 23
Total with taxes and fees
Lakefront Boho Tiny House
Beach

13. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
$262 nightly
The price is $296
Sep 15 - Sep 16
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach

14. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$276 nightly
The price is $312
Sep 22 - Sep 23
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Outdoor dining

15. 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
9.6 out of 10, Exceptional, (61 reviews)
"Beautfil and convenient place. We stayed just one night and the location is perfect since it's just by the Spa."
United States
Aura
$222 nightly
The price is $251
Sep 23 - Sep 24
Total with taxes and fees
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Exterior

16. Grey comfort room

Grey comfort room
New London
10.0 out of 10, Exceptional, (1 review)
"Muy bien servicio"
United States
Eduin Vicente
$104 nightly
The price is $116
Aug 31 - Sep 1
Total with taxes and fees
Grey comfort room
Apartment (0 Bedroom) | Interior

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Cozy Studio: Indoor Hot Tub & Inground Pool Access
3.0 star property
Montville
10.0 out of 10, Exceptional, (1 review)
"Everything from the price,location,tranquility, and the host Allen was awesome. We would go back in a heartbeat. Montville is beautiful."
United States
Eduardo
$374 nightly
The price is $430
Aug 26 - Aug 27
Total with taxes and fees
Cozy Studio: Indoor Hot Tub & Inground Pool Access
Living area

18. 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, (14 reviews)
"great place to stay"
United States
christopher
$300 nightly
The price is $339
Sep 9 - Sep 10
Total with taxes and fees
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Dining

19. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
$703 nightly
The price is $795
Sep 9 - Sep 10
Total with taxes and fees
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Exterior

20. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
$278 nightly
The price is $296
Aug 29 - Aug 30
Total with taxes and fees
All New 1BR with tons of Charm
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

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

8/10 Good
"Great experience my pet loved it and was very comfortable"
Herbert 2-night trip
Posted 4 hours ago
Motel 6 New Haven - Branford, CT

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 $144 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.

Explore a world of travel with Expedia

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?

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street: This vacation home rental near Chester is located on the waterfront and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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, Chester Creek Marina and Connecticut Valley Railroad State Park Trail 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.