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Compare 793 Vacation Homes in Stevensville with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (212)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (75)
"Great for the price. The motel of VRBOs would be my best description. Plenty of space for what we needed though and no issues during our stay. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes

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

10.0 out of 10, Exceptional, (184)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

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

9.6 out of 10, Exceptional, (27)
"Great stay, would do it again."
The price is AED 228
AED 880 total
includes taxes & fees
28 Apr - 29 Apr
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"This house was in a fantastic location! It is within walking distance to downtown Annapolis and anything you might need or want. It is a cute little home with all of your needed comforts. "
Historic Annapolis Home 1.5 blocks from center of town.

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (73)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage

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

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

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

9.8 out of 10, Exceptional, (34)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

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

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

2.5 star property
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"
Steps to USNA Gate 3 at historic Gatehouse, on-site parking

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (197)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Would stay again."
The Lazy Crab Beach House - Free beach passes

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 251
AED 889 total
includes taxes & fees
29 Apr - 30 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (47)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
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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Other property types in Stevensville

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"We had a wonderful stay on this luxurious houseboat! Clean, comfortable & fun and Julia is an excellent host. We highly recommend Julia's Arc!"
Chesapeake Houseboat Getaway on Kent Island, Maryland

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

10.0 out of 10, Exceptional, (184)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (40)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
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.