Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chester vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Jun 29 - Jun 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (23 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$255 nightly
The price is $281
Jun 24 - Jun 25
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$349 nightly
The price is $385
Jun 25 - Jun 26
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
$311 nightly
The price is $336
Jun 29 - Jun 30
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
$305 nightly
The price is $329
Jun 29 - Jun 30
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (14 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$258 nightly
The price is $273
Jul 16 - Jul 17
Total with taxes and fees
BAYSIDE BUNGALOW
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$373 nightly
The price is $425
Jun 30 - Jul 1
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
$343 nightly
The price is $364
Jun 29 - Jun 30
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Smart TV

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
3-bedroom house in Deale located on Bay many amenities and great views
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
$263 nightly
The price is $300
Jun 24 - Jun 25
Total with taxes and fees
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
$339 nightly
The price is $374
Jun 29 - Jun 30
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Terrace/patio

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Arnold
9.6 out of 10, Exceptional, (10 reviews)
"Great place!"
United States
Chris A.
$312 nightly
The price is $355
Jun 30 - Jul 1
Total with taxes and fees
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
$326 nightly
The price is $372
Jul 20 - Jul 21
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.2 out of 10, Wonderful, (10 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
$206 nightly
The price is $234
Jun 28 - Jun 29
Total with taxes and fees
Cute, Cozy 2-bedroom house near Annapolis with water access
Smart TV, fireplace

RELAX- Eastern Shore Creek Home - 6 Guests

RELAX- Eastern Shore Creek Home - 6 Guests
Grasonville
10.0 out of 10, Exceptional, (6 reviews)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$633 nightly
The price is $722
Jun 26 - Jun 27
Total with taxes and fees
Family Home on Mayo Peninsula | Deck | Sleeps 10
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
$602 nightly
The price is $613
Jul 6 - Jul 7
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
$269 nightly
The price is $274
Jun 24 - Jun 25
Total with taxes and fees
Sailboat Experience in Annapolis
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$600 nightly
The price is $684
Jul 20 - Jul 21
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
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

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

8/10 Good
"Nice stay and staff very helpful."
Edward 1-night trip
Posted less than an hour ago
Courtyard by Marriott Annapolis

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 $234 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

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation rentals that Chester has to offer?

St. Michaels Escape | Pool, Hot Tub & Fire Pit: This vacation home 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chester?

Choose from 9 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Chesapeake Bay Environmental Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.