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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (175 reviews)
"Beautiful view, very clean !"
United States
Karolyne
$224 nightly
The price is $258
Sep 7 - Sep 8
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.
$255 nightly
The price is $289
Aug 26 - Aug 27
Total with taxes and fees
Walk To Goodspeed Opera House!
1 bedroom, desk, iron/ironing board, travel crib

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
$216 nightly
The price is $245
Sep 7 - Sep 8
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, fireplace, books, music library

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, (34 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.
$226 nightly
The price is $256
Aug 31 - Sep 1
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Coffee/tea maker, fridge, microwave, oven

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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$310 nightly
The price is $351
Sep 1 - Sep 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly
Sun loungers, beach towels

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
$322 nightly
The price is $364
Aug 24 - Aug 25
Total with taxes and fees
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Property grounds

7. 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.
$265 nightly
The price is $300
Sep 7 - Sep 8
Total with taxes and fees
Lakeview Carriage House with Spectacular Sunset Views
Beach nearby

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.
$340 nightly
The price is $385
Aug 9 - Aug 10
Total with taxes and fees
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Interior

9. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$429 nightly
The price is $485
Aug 11 - Aug 12
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Dining

10. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$228 nightly
The price is $259
Aug 11 - Aug 12
Total with taxes and fees
2BR Apartment Near Wesleyan 102
1 bedroom, WiFi (free), bed sheets

11. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (8 reviews)
"Every thing was amazing "
United States
Annaliaa C.
$287 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Lakefront Boho Tiny House
Smart TV

12. #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.
$432 nightly
The price is $463
Aug 11 - Aug 12
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
Exterior

13. 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.
$300 nightly
The price is $339
Sep 1 - Sep 2
Total with taxes and fees
Cozy Lakefront Tiny House
Exterior

14. Grey comfort room

Grey comfort room
New London
10.0 out of 10, Exceptional, (1 review)
"Muy bien servicio"
United States
Eduin Vicente
$99 nightly
The price is $111
Aug 31 - Sep 1
Total with taxes and fees
Grey comfort room
Beach nearby

15. 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
$288 nightly
The price is $324
Aug 10 - Aug 11
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds

16. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
United States
Rodrigo C.
$369 nightly
The price is $400
Aug 9 - Aug 10
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Smart TV

17. 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.
$176 nightly
The price is $199
Aug 12 - Aug 13
Total with taxes and fees
The Tiny Cottage & Mini Farm
1 bedroom, iron/ironing board, WiFi, bed sheets

18. 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, (14 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
Aug 13 - Aug 14
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Exterior

19. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$274 nightly
The price is $292
Aug 11 - Aug 12
Total with taxes and fees
All New 1BR with tons of Charm
TV

20. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
$274 nightly
The price is $292
Aug 13 - Aug 14
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
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

Hampton Inn Norwich

Hampton Inn Norwich

8/10 Good
"The room, common areas, and breakfast area were very clean."
Shakira 1-night trip
Posted 2 hours ago
Hampton Inn Norwich

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.