Vacation Rentals & Estates in Baltimore

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Waterfront Views and a Sandy Beach

Betterton condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool Water sports

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Price per night from

$402

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1 of 2 match: Swimming pool, Water sports

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Price per night from

$178

Private Beach Access, Onsite Kayaks and Shared Boat Ramp

Chestertown house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$259

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

1 of 2 match: Swimming pool, Water sports

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Price per night from

$453

Nice ambient 5BDR with fast WiFi near Airport & Casino

Riviera Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Swimming pool, Water sports

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Price per night from

$574

Historic Riverside Cottage

Ellicott City house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swimming pool, Water sports

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Price per night from

$316

King George Downtown Annapolis Getaway

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$431

Gwendolyn's Marigold Manor 2 bedroom "Cottage"

Port Deposit cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$258

B-More Downtown Rowhouse

Baltimore townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$242

City Living in a Park-Like Setting

Pikesville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 14 minutes

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$172

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$476

Sweet Suite!

Hampden apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$85

Serene Waterfront Apartment on Kent Island

Stevensville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swimming pool, Water sports

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Price per night from

$229

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Water sports, Swimming pool

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Price per night from

$442

Modern Lux Suites W/pool View Free Parking & Wifi

Baltimore apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Water sports, Swimming pool

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Price per night from

$201

Sunny art filled apartment in historic downtown Baltimore

Baltimore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Water sports, Swimming pool

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Price per night from

$102

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$403

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.

1 of 2 match: Swimming pool, Water sports

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Price per night from

$458

Spacious Studio 3 Mins Inner Harbor

Baltimore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Water sports, Swimming pool

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Price per night from

$167

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$540

Luxury Highrise

Baltimore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$198

A WELL SEASONED APT IN TOWSON BALTIMORE

Towson apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$265

SOPHISTICATED APARTMENT IN TOWSON

Towson apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$253

Beautifuf, renovated condo in Downtown Silver Spring -10 mins from Washington DC

Silver Spring apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$172

Quiet House on Cul de Sac

Rockville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$401

1 of 2 match: Swimming pool, Water sports

1 of 2 filters match

Price per night from

$114

City Gem

Baltimore apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$168

Luxurious Getaway!!

Olney house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$287

Cozy Upscale Apartment tip of D.C!!

Glenmont apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 1

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$29

Annapolis Area Shagrila Resort

Davidsonville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$916

The Annapolis General House

Parole house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$690

Free Parking with private fenced-in backyard with pool table at Weekender

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$292

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$407

Cozy Cool Spring waterfront apartment with pier mins to Annapolis

Arnold apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$177

Private pier and pool at this waterfront Chestertown home

Chestertown house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$458

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$725

Stay poolside for 2024 Commissioning Week! Pier & parking mins to USNA

Arnold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$382

2 Bedroom Fully Furnished APT over Camden Yards

Baltimore apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 25 minutes

1 of 2 match: Water sports, Swimming pool

1 of 2 filters match

Price per night from

$263

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