Book Holiday Homes in Grasonville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Grasonville

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA

Annapolis
This vacation home is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval Academy.
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Save an average of 15% on thousands of hotels when you're signed in
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Harbor.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming townhome with AC and WiFi in delightful Annapolis

Charming townhome with AC and WiFi in delightful Annapolis

Annapolis
The price is AU$117 per night from 6 Sept to 7 Sept
AU$117
6 Sept - 7 Sept
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of Annapolis City Dock and U.S. Naval Academy.
Charming townhome with AC and WiFi in delightful Annapolis
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 out of 5
Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Heated pool, sandy beach, pier, and playground set punch point apart!

Heated pool, sandy beach, pier, and playground set punch point apart!

Sherwood
Located in Sherwood, this vacation home is on the waterfront, a 3-minute drive from Goat Island and 7 minutes from Back Creek Community Park.
Heated pool, sandy beach, pier, and playground set punch point apart!
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
With a stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Kings Town Park and Historical Society of Kent County Maryland.
Pet-Friendly Home on Chester River w/ Dock!
Don't see what you're looking for?
See all available properties in Grasonville
View all properties
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.

Grasonville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Grasonville vacation homes are the perfect way for you to wing it.

Holiday houses in Grasonville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Grasonville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Grasonville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Grasonville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Grasonville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Grasonville Holiday Homes essential information

Accommodation
659 Holiday Homes
Lowest Price
AU$117
Highest Price
AU$270
Popular accommodation
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming townhome with AC and WiFi in delightful Annapolis, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , Heated pool, sandy beach, pier, and playground set punch point apart!, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Pet-Friendly Home on Chester River w/ Dock!

Top trending hotels in Grasonville

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 21 Aug to 22 Aug
AU$270
21 Aug - 22 Aug
includes taxes & fees
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
3206 Main St, Grasonville, MD
The price is AU$260 per night from 1 Sept to 2 Sept
AU$260
1 Sept - 2 Sept
includes taxes & fees
A stay at Hilton Garden Inn Kent Island Marina places you in the heart of Grasonville, a 3-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hilton Garden Inn Kent Island Marina
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 19 Aug to 20 Aug
AU$185
19 Aug - 20 Aug
includes taxes & fees
A stay at Best Western Kent Narrows Inn places you in the heart of Grasonville, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island ...
Best Western Kent Narrows Inn
Save an average of 15% on thousands of hotels when you're signed in
Quality Inn

Quality Inn

2.5 out of 5
101 Vfw Ave, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 24 Aug to 25 Aug
AU$166
24 Aug - 25 Aug
includes taxes & fees
Located in Grasonville, Quality Inn is a 5-minute drive from Chesapeake Exploration Center and 6 minutes from Queenstown Premium Outlets.
Quality Inn
Don't see what you're looking for?
See all available properties in Grasonville
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.