Annapolis Houses | FlipKey Vacation Rentals

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Match: Rental types

All filters match

Price per night from

$573

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

Match: Rental types

All filters match

Price per night from

$548

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 41 minutes

Match: Rental types

All filters match

Price per night from

$327

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 27 minutes

Match: Rental types

All filters match

Price per night from

$288

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 59 minutes

Match: Rental types

All filters match

Price per night from

$859

Annapolis Townhome w/Deck by Nature Trails & River

Annapolis house

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 56 minutes

Match: Rental types

All filters match

Price per night from

$102

Charming Eastport Home

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$344

Charming Artists Home in Eastport/Annapolis

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$430

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Match: Rental types

All filters match

Price per night from

$716

Beautiful Murray Hill Home (Annapolis)

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Match: Rental types

All filters match

Price per night from

$490

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$1,145

Your Eastport Annapolis Haven!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 9 minutes

Match: Rental types

All filters match

Price per night from

$484

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

Match: Rental types

All filters match

Price per night from

$796

Annapolis Home w/ Bay Views - Near Naval Academy!

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 5 minutes

Match: Rental types

All filters match

Price per night from

$831

Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

Match: Rental types

All filters match

Price per night from

$366

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$516

Charming Home close to historic district

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$287

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 9

Match: Rental types

All filters match

Price per night from

$412

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$461

Beautiful Home in Nice Community with up to 7 bedrooms

Severn house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 15 minutes

Match: Rental types

All filters match

Price per night from

$444

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 56 minutes

Match: Rental types

All filters match

Price per night from

$144

Lovely Residential Home

Brooklyn Park house

3 bedrooms / 1 bathroom / sleeps 6

Match: Rental types

All filters match

Price per night from

$126

Summer House in Rock Hall

Rock Hall house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 1 hour 56 minutes

Match: Rental types

All filters match

Price per night from

$327

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$573

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$344

Upscale House/12 MINUTES FROM DC

Bowie house

5 bedrooms / 3 bathrooms / sleeps 16

Match: Rental types

All filters match

Price per night from

$561

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

Match: Rental types

All filters match

Price per night from

$115

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that you could ever need and is very unique and quaint. The location is more than perfect (we literally were in walking distance of everything, shops, restaurants, etc.) and did not even have to get into the car to drive anywhere the entire time. The backyard has a wonderful porch where you can sit outside and converse with friends or even sip your coffee in the morning. The view is phenomenal! You have a wonderful panoramic view of the water from your bedroom window and the beds are very comfortable (which is a must for me). If you are planning on a trip to experience St. Michael's whether it is a romantic weekend getaway or a family (group) outing I would hands down recommend this house.

Responds fast! avg. 3 hours 23 minutes

Match: Rental types

All filters match

Price per night from

$447

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$372

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$573

Close to Baltimore, Annapolis and Washington D.C.

Glen Burnie house

4 bedrooms / 2 bathrooms / sleeps 13

Match: Rental types

All filters match

Price per night from

$343

4,000 Sq Ft Annapolis Area Home w/ Backyard Oasis!

Riva house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Match: Rental types

All filters match

Price per night from

$430

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

Chester house

4 bedrooms / 3 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$401

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 56 minutes

Match: Rental types

All filters match

Price per night from

$229

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Match: Rental types

All filters match

Price per night from

$287

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Match: Rental types

All filters match

Price per night from

$481

Modern Luxury Rental in North Beach!

North Beach house

1 bedroom / 1 bathroom / sleeps 4

Match: Rental types

All filters match

Price per night from

$126

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable. I have visited this cottage several times and will continue to do so! A great place to gather with family and friends or a quick weekend escape to enjoy life on the shore.

Responds fast! avg. 3 hours 23 minutes

Match: Rental types

All filters match

Price per night from

$224

Houses Annapolis

Per night

53 houses

Viewing 38 of 53houses in Annapolis

Viewing 38 of 53
houses in Annapolis