Chester Vacation Rentals from $121: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Chester?

Thames River Retreat · CT College+Casinos+USCGA : This vacation home rental near Chester is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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In two weeks

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Our top choices for Chester vacation rentals

Cabin in East Haddam

Simge

$159 nightly

Dec 14 - Dec 15

Total with taxes and fees

Apartment in Old Lyme

Lylian

$171 nightly

Jan 2 - Jan 3, 2026

Total with taxes and fees

Vacation Home in Salem

nic

$318 nightly

Dec 15 - Dec 16

Total with taxes and fees

Cottage in Clinton

michelle

$159 nightly

Dec 15 - Dec 16

Total with taxes and fees

Mobile Home in East Lyme

Tatyanna R.

$183 nightly

Dec 18 - Dec 19

Total with taxes and fees

Vacation Home in Old Lyme

Katy C.

$356 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Vacation Home in Waterford

Elaine A.

$319 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Mobile Home in East Lyme

Rebecca K.

$206 nightly

Dec 12 - Dec 13

Total with taxes and fees

Vacation Home in Montville

Bonnie H.

$237 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Vacation Home in Montville

Anonymous traveler

$303 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Vacation Home in New London

Suzanne M.

$168 nightly

Dec 15 - Dec 16

Total with taxes and fees

Vacation Home in East Lyme

Sarah G.

$321 nightly

Jan 5 - Jan 6, 2026

Total with taxes and fees

Vacation Home in Middletown

"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "

Nichole N.

$275 nightly

Dec 14 - Dec 15

Total with taxes and fees

Villa in Norwich

Brooke

$249 nightly

Dec 14 - Dec 15

Total with taxes and fees

Villa in Norwich

Bill M.

$230 nightly

Dec 14 - Dec 15

Total with taxes and fees

Villa in Norwich

Johnny B.

$236 nightly

Dec 16 - Dec 17

Total with taxes and fees

Vacation Home in Waterford

Michelle M.

$326 nightly

Dec 12 - Dec 13

Total with taxes and fees

Apartment in Berlin

"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "

Theresa G.

$246 nightly

Dec 14 - Dec 15

Total with taxes and fees

Cottage in Waterford

Jorie M.

$265 nightly

Dec 14 - Dec 15

Total with taxes and fees

Apartment in Wallingford

ROBERT P.

$271 nightly

Dec 12 - Dec 13

Total with taxes and fees

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Top Chester Hotel Reviews

Mohegan Sun

10/10 Excellent

"Everything"

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent

"Small but very clean room, extremely pleasant front desk staff, simple breakfast with 24 hour coffee, and more than adequate parking. The price was definitely right, and I would stay here again if passing through. Note… There’s a fridge in the room, but no microwave. You can use the microwave in the lobby."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, so this was perfect for me. Much more reasonable than the other places in the area. Depends on what you’re looking for. Won’t hesitate to come back again!"

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 $121 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.

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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?

Thames River Retreat · CT College+Casinos+USCGA: This vacation home rental near Chester is located on a river and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.

Chester Vacation Rentals

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Check prices for these dates

Our top choices for Chester vacation rentals

Cabin in East Haddam

Apartment in Old Lyme

Vacation Home in Salem

Cottage in Clinton

Mobile Home in East Lyme

Vacation Home in Old Lyme

Vacation Home in Waterford

Mobile Home in East Lyme

Vacation Home in Montville

Vacation Home in Montville

Vacation Home in New London

Vacation Home in East Lyme

Vacation Home in Middletown

Villa in Norwich

Villa in Norwich

Villa in Norwich

Vacation Home in Waterford

Apartment in Berlin

Cottage in Waterford

Apartment in Wallingford

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Mohegan Sun

Find out more about Chester

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