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
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
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
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
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 NZ$468 per night from 7 Apr to 8 Apr
NZ$468
includes taxes & fees
7 Apr - 8 Apr
Stay at this vacation home in Stevensville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Matapeake State Park and Paul Reed Smith Guitars are ...
❤️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
Stay at this vacation home in Annapolis. Enjoy free WiFi, patios, and in-room jetted tubs. Popular attractions Ellen O. Moyer Nature Park at Back Creek and Banneker ...
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
Stay at this vacation home in Rock Hall. Enjoy free WiFi, a garden, and patios. Popular attractions The Mainstay and Rock Hall Harbor are located nearby.
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
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Muskrat Park and Higgins Yacht Yard and ...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Your Annapolis Adventure Starts Here!!

Your Annapolis Adventure Starts Here!!

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a beach locale, and a water park. Our guests praise the helpful staff in our ...
Your Annapolis Adventure Starts Here!!
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
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
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
Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Hammond-Harwood House and Alumni Hall are located nearby.
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
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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
672 Holiday Homes
Lowest Price
NZ$175
Highest Price
NZ$468
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, Your Annapolis Adventure Starts Here!! , Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Steps to USNA Gate 3 at historic Gatehouse, on-site parking

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 NZ$263 per night from 27 Apr to 28 Apr
NZ$263
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
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 NZ$246 per night from 7 Apr to 8 Apr
NZ$246
includes taxes & fees
7 Apr - 8 Apr
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
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 NZ$175 per night from 14 Apr to 15 Apr
NZ$175
includes taxes & fees
14 Apr - 15 Apr
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Kent Narrows Inn
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Holiday Inn Express Annapolis - Kent Island by IHG

Holiday Inn Express Annapolis - Kent Island by IHG

2.5 out of 5
1020 Kent Narrows Rd, Grasonville, MD
Fully refundable
The price is NZ$185 per night from 6 Apr to 7 Apr
NZ$185
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express Annapolis - Kent Island by IHG
Don't see what you're looking for?
See all available properties in Grasonville
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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.