Vacation rentals in Booby Point

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Top-rated vacation rentals in Booby Point

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Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.

Dec 6 – 13

ﺩ.ﺇ346 per night

Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 128 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

Apr 20 – 27

ﺩ.ﺇ586 per night

Guest favorite

Cottage in Essex

5.0 out of 5 average rating, 27 reviews

The Little House of Rockaway Beach, Maryland

Unwind at this new home in a quiet, safe neighborhood on the Chesapeake Bay. Designed by the host, the house is decorated with a mix of vintage and new items lovingly chosen to create an eclectic coastal cottage. Four adults (no pets) will sleep comfortably on a queen bed and a sleep sofa w/queen mattress. The clean and modern kitchen is fully equipped. Enjoy water views from the attached deck or walk a short distance to the waterfront where a designated deck offers seating and water sport gear.

May 20 – 27

ﺩ.ﺇ745 per night

Guest favorite

Bungalow in Baltimore

4.96 out of 5 average rating, 154 reviews

RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

May 30 – Jun 6

ﺩ.ﺇ334 per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 562 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul 6 – 13

ﺩ.ﺇ411 per night

Guest favorite

Apartment in Baltimore

4.99 out of 5 average rating, 250 reviews

ButchersHill, Clean, Cozy Fireplace and Private!

My name is John S Marsiglia. I Clean and disinfect between each guest! Private, self checkin , historic 2207 E Baltimore St. See me and the listing online. Fully furnished, Enjoy remote control gas log fireplace, New King mattress, 50" 4K smart TV with surround sound, Xfinity,Netflix, Free top speed WiFi, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, 12Ft ceilings, modern beautiful bathroom, dual shower heads&seats, private full size front load W&D,walk-in closet.Pets?

Sep 23 – 30

ﺩ.ﺇ427 per night

Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 109 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Feb 20 – 27

ﺩ.ﺇ376 per night

Guest favorite

Guesthouse in White Marsh

4.97 out of 5 average rating, 140 reviews

Bird River Bottega - A Waterfront Oasis!

Private entrance studio located on a waterfront property. The Bottega is perfect for couples, solo travelers, and business professionals; best suited for two travelers. Enjoy your morning coffee by the water and watch the Ospreys, herons, ducks, hawks, and bald eagles galore. Whether you are fishing, lounging, or kayaking the Bird River (home to the Chesapeake Bay), you are bound for relaxation. Surrounded by a plethora of eateries, shopping, and entertainment all within a 25 minute drive.

Oct 28 – Nov 4

ﺩ.ﺇ331 per night

Guest favorite

Cottage in Glen Burnie

4.92 out of 5 average rating, 140 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Jan 12 – 19

ﺩ.ﺇ295 per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Oct 1 – 8

ﺩ.ﺇ514 per night

Guest favorite

Guest suite in Joppatowne

5.0 out of 5 average rating, 81 reviews

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe and dresser. Washer/dryer available upon request.

May 12 – 19

ﺩ.ﺇ277 per night

Guest favorite

Farm stay in Essex

4.95 out of 5 average rating, 139 reviews

Private wing at historic water view Walnut Grove

Enjoy your stay in the private guest wing of the historic Walnut Grove farmhouse with separate heating and cooling. Wildlife, chickens, rooster and pets in our little farm. Beautiful sunrises and sunsets viewed from the property or the dock across the street. 12 miles to Baltimore and 5 miles from 95. Local dining, shopping, parks, and golf course. NON-SMOKERS ONLY. No smoking or vaping on Property. Must agree to follow all rules.

Sep 13 – 20

ﺩ.ﺇ412 per night