Book Holiday Homes in Grasonville

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Featured Holiday Homes in Grasonville

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!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Love Point State Park and 7 minutes from Paul Reed Smith Guitars.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
The price is AU$764 per night from 27 May to 28 May
AU$764
includes taxes & fees
27 May - 28 May
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.
Historic Annapolis Home 1.5 blocks from center of town.
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2 out of 5
Annapolis
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 out of 5
Annapolis
Steps to USNA Gate 3 at historic Gatehouse, on-site parking is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval ...
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and John Smith House.
PERFECT LOCATION in the heart of history
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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
673 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$764
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history

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$224 per night from 27 Apr to 28 Apr
AU$224
includes taxes & fees
27 Apr - 28 Apr
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
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$169 per night from 27 Apr to 28 Apr
AU$169
includes taxes & fees
27 Apr - 28 Apr
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
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$241 per night from 27 Apr to 28 Apr
AU$241
includes taxes & fees
27 Apr - 28 Apr
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
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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$148 per night from 27 Apr to 28 Apr
AU$148
includes taxes & fees
27 Apr - 28 Apr
Located in Grasonville, Quality Inn is a 5-minute drive from Chesapeake Exploration Center and 6 minutes from Queenstown Premium Outlets.
Quality Inn
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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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^Subject to availability and chosen travel dates.