Photo by Jennifer Crim

Stevensville Vacation Rentals

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Browse Select Stevensville Vacation Homes

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

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

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Calloway Drive Retreat | House in Shady Side

9.2 out of 10, Wonderful, (5)
"We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier."
Calloway Drive Retreat | House in Shady Side

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

Private Waterfront Woods | Dock, Kayaks, Views

9.8 out of 10, Exceptional, (15)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (72)
"House is exceptionally clean. Hosts are very responsive to questions. House is very well supplied and convenient to most of Annapolis. House is as advertised. "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (13)
"We very much enjoyed our stay. The house is exactly as described and we would stay here again if we are in Annapolis again. The house has everything you need with a fully equipped kitchen, smart tvs in every room, and the beds are very comfortable. There is so much parking and the house is walking distance to everything in downtown Annapolis and the Naval Academy. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (3)
"From communication to check-in and cleanliness, this VRBO has plenty of room and modern amenities. What put this over the top was that a party member left the wallet at the VRBO, and the renters went and retrieved the wallet and met us to return it. They went above and beyond to help us. It has a good backyard and can park 3-4 cars in the driveway; this VRBO has everything. Easily five stars"
Brand New Spacious Luxury Home

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (32)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is CA $119
CA $374 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

10.0 out of 10, Exceptional, (102)
"Awesome House Awesome neighborhood Awesome Host(ess). 10 out of 10"
The price is CA $575
CA $746 total
includes taxes & fees
Jan 12 - Jan 13, 2025
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

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

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Walk to Everything House

10.0 out of 10, Exceptional, (74)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (27)
"Felt like home as soon as we walked in...except it was CLEANER than home :-) Comfortable, spacious, well-stocked. Hosts were attentive & quick to answer messages. Great experience!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Bennett House (entire):Haven in Historic Annapolis

10.0 out of 10, Exceptional, (12)
"Great place, wonderful location "
Bennett House (entire):Haven in Historic Annapolis

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
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

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (32)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is CA $119
CA $374 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Relax on Kent Island in 3 Bedroom Home w/Waterview

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.6 out of 10, Exceptional, (20)
"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
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.