Aerial view of Kent Narrows peninsula inlet on Chesapeake in Grasonville Maryland, beach houses with private long docks for the sailboats line a road curving like an S shape with blue sky and water

Grasonville Vacation Rentals

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Our top choices for Grasonville vacation rentals

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
$395 nightly
The price is $419
Jun 24 - Jun 25
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

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

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
$255 nightly
The price is $270
Jun 24 - Jun 25
Total with taxes and fees
BAYSIDE BUNGALOW

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
$381 nightly
The price is $434
Jun 30 - Jul 1
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

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!

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!

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!

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$452 nightly
The price is $515
Jul 15 - Jul 16
Total with taxes and fees
Waterfront Oasis of Annapolis Star

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

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

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

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

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
$605 nightly
The price is $616
Jul 6 - Jul 7
Total with taxes and fees
Sunset Cottage - West River Access and Views!

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Jun 29 - Jun 30
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
$715 nightly
The price is $815
Jul 1 - Jul 2
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Jul 1 - Jul 2
Total with taxes and fees
Turnbridge Manor

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

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
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 Grasonville Hotel Reviews

Find out more about Grasonville

Everything you need to know about Grasonville 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 Grasonville 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 Grasonville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Grasonville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Grasonville. 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 Grasonville 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 $159 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 Grasonville rentals

At Expedia, we put the best Grasonville 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 Grasonville 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 Grasonville 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 Grasonville. 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

Can I find vacation rentals in Grasonville?

Yes, there are vacation rentals close to top sights in Grasonville, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and marina in Grasonville. Leave plenty of time to check out the shops and beaches during your trip.

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

St. Michaels Escape | Pool, Hot Tub & Fire Pit: You might want to consider this vacation home rental near Grasonville, which 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 are there in Grasonville?

Choose from 11 Expedia vacation rentals in Grasonville for a memorable vacation.

What can I see and do in Grasonville?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Chesapeake Bay Environmental Center. Queenstown Harbor Golf and Queenstown Premium Outlets are a couple of places you'll find in the larger area.

What are vacation rentals like in Grasonville?

Vacation rentals are private accommodations you can reserve for a short or long stay in Grasonville. Vacation rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.