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Match: Rental types Swing set or jungle gym

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Price per night from

$492

Match: Rental types Swing set or jungle gym

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Price per night from

$29

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,296

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,869

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$401

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$402

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,296

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Price per night from

$114

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

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Price per night from

$861

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DC. Baltimore. Annapolis *Suite in on the main fl.

Highland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$115

City Living in a Park-Like Setting

Pikesville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 14 minutes

1 of 2 match: Rental types, Swing set or jungle gym

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Price per night from

$173

Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

Fishing Creek apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and more. The décor was adorable, though both aesthetically and functionally vintage. We found a very thoughtful welcome bag and bottle of wine on the dining table as soon as we walked in. A variety of items found throughout the house make for a very comfortable and carefree stay (including a blender, coffee maker, coffee, a wide variety of DVD/VHS movies, and more). The kitchen was fully stocked with all of the essentials, as well as a great assortment of spices. It truly feels like your home away from home. Fishing Creek is a modest town, but houses some of the friendliest people. There is only one general store and one restaurant – both terrific. We arrived at the general store five minutes after closing and they still opened the doors for us. The restaurant, Old Salty’s, has fast, friendly, and accommodating service and the food is very good. Not to mention, the largest and cleanest oysters we have ever tried. We spent much of our time relaxing and enjoying the amenities that the Haven provides. The screened porch makes for a wonderful place to have an outdoor dinner. The fire pit in the back kept us warm as we took in some of the most beautiful sunsets we have ever seen. We even caught a few crabs just off the dock up front, using the crab traps that Debi provided. Unfortunately, we found no luck with catching any fish. Debi was out of town during our stay, yet she still provided wonderful service. Her responses to text messages and e-mails were always very prompt. She left the Haven very tidy for us, and included a detailed instruction manual that covered scenario we may have come across. It’s obvious she puts a lot of thought into giving her guests a pleasant stay, and it surely pays off. We really enjoyed our time at the Haven, and have already talked about a possible return trip in the future. Thanks Debi!

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Price per night from

$207

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Price per night from

$104

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

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Price per night from

$7,460

3 bed 2 bath in West O C, Md. Pool. Near Marinas in West OC

Ocean City townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$230

OCEANFRNT 3 Br N. O.C Luxury Slp.6 - SeaWatch# 915

Ocean City apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very nice.” Beach access was great. Lot's of fun activities. Great views of the water. loved watching the dolphins along the shore.

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Price per night from

$537

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Price per night from

$316

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$718

Rosewood Manor BnB

Port Tobacco house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$309

Lancaster House in Fell's Point

Baltimore house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$339

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.

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Price per night from

$488

Beautiful Ocean City Home for Rent

Ocean City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

“Not sure what this is asking” Very nice , quiet, plenty of room. Felt very comfortable there . Would definetly go back. I had my three grandsons and they really enjoyed their stay. Loved having more than one bathroom.

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$241

“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.

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$454

All you need near DC/AIRP/Silver Spring; 3br/2ba

Silver Spring house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$218

Spacious home with 8 to 12 bedrooms & 5 to 8 bathrooms, a gym & movie theater

Burtonsville house

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 36

Responds fast! avg. 2 hours 0 minutes

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Price per night from

$1,090

White Oak Retreat

Swanton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

“Lovely place for family vacation!” This spacious log house was a perfect fit for our first family trip to Deep Creek. We had plenty of room for our group of 11 people (3 couples and 5 single adults). Everyone was pleased with the accommodations. It was clean, spacious and well equipped. John & Kathy Joyce were a pleasure to deal with. They were very helpful from beginning to end. We had such a good time that we hope to visit again next year.

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Price per night from

$402

Rock Haul

Swanton house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

“Relaxing at the lake!!” Peaceful and quiet. Plenty of room for family. Right on the lake. Kitchen has everything needed to cook. Cozy and clean with rustic charm!!

1 of 2 match: Swing set or jungle gym, Rental types

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Price per night from

$402

Ocean block townhouse in North Ocean City

Ocean City house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“Always Amazing” We love staying in Beach Mist #5. Being mere seconds from the beach is heavenly, but it is also nice to lay out on the beautifully decorated deck and relax. We also love being close to tax-free shopping in Delaware. It is a nice, quiet spot that doesn't have a lot of traffic buzzing by, but everything from Billy's to the boardwalk is easily accessible. We cannot wait to come back.

1 of 2 match: Swing set or jungle gym, Rental types

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Price per night from

$353

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

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Price per night from

$1,032

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

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$477

Beach, Bay & Bicycle

Ocean City house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$451

Quiet P/F Cul de Sac back to nature

Upper Marlboro house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Rental types

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Price per night from

$201

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.

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Price per night from

$459

Johns Hopkins Doctors Welcome (3 Minute Walk to J)

Baltimore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$68

Deep Creek Log Home Sleeps 10

McHenry house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$287

Grove Guest Home

Frederick house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$218

The Sweet Home near Washington DC

Highland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 11 minutes

1 of 2 match: Swing set or jungle gym, Rental types

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Price per night from

$104

Kingsbay 'Bayhouse' Vacation Rental

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,142

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