Vacation rentals in Deale

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Top-rated vacation rentals in Deale

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern apartment features a treehouse-style deck that is surrounded by leafy trees. The exterior showcases a combination of dark wood and neutral siding, while large windows allow natural light to enter the space.
Loft in Riva
4.95 out of 5 average rating, 132 reviews

New Loft w/South River view from treehouse deck!

Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

Guest favorite
A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.
Cottage in North Beach
4.91 out of 5 average rating, 117 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Top guest favorite
Home in Deale
4.99 out of 5 average rating, 163 reviews

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Cook wonderful meals in our well-equipped kitchen. Or try some our local restaurants. Great place for families or multi family groups.

Guest favorite
A comfortable living area features a plush blue sofa with pink accent pillows, complemented by a round mirror. Decorative plants add a touch of greenery. A light wooden coffee table supports a floral arrangement, while two poufs create additional seating in a welcoming space.
Townhouse in North Beach
4.96 out of 5 average rating, 222 reviews

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

Top guest favorite
A close-up view of the sleeping area features a full bed with an earthy-toned quilt and decorative pillows. A soft throw blanket rests at the foot of the bed. Above, a series of wooden wall art pieces adds a touch of warmth, while a 55-inch Smart TV is mounted nearby.
Apartment in Bowie
4.93 out of 5 average rating, 147 reviews

Just Like Home - Private Entrance Apt in DMV Area

288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sofa, roll-away single bed, kitchen, bathroom with small shower stall & 55” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Excellent location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

Top guest favorite
The open living space is furnished with a dark sectional couch and a glass dining table surrounded by patterned chairs. Natural light enters through a window, illuminating the wooden flooring and creating a welcoming ambiance.
Guesthouse in Bowie
4.86 out of 5 average rating, 125 reviews

Renovated Basement with Private Entrance

Fully renovated & updated basement with a full set of windows and sunlight. House is in a very nice and safe neighborhood. Walk-out basement with Private Entrance. Plenty of Parking. Non smoking. All Utilities and Wi-Fi are included. • Total Area: 800 Sq.ft. • One Bedroom with closet • Full Bathroom • Fully Furnished • Kitchen • Dining Area • Walk out Basement – Above ground (Private Entrance) • No Owen • No Dishwasher • No Washer and Dryer • Plenty of Parking • No Smoking

Top guest favorite
The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.
Home in West River
4.97 out of 5 average rating, 148 reviews

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Guest favorite
A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.
Apartment in Deale
4.91 out of 5 average rating, 620 reviews

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis or other local walks. Fully relax with pier, kayaks, hot tub, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Top guest favorite
The cottage features a welcoming exterior with a combination of siding and a shingled roof. A well-maintained lawn surrounds the home, and landscaping includes a variety of shrubs. Large windows are visible on the front, providing ample natural light.
Home in Deale
4.99 out of 5 average rating, 155 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale
4.95 out of 5 average rating, 169 reviews

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

Top guest favorite
A cozy living area is highlighted by red sofas and a decorative coffee table. A cheerful lamp casts warm light, while natural light filters through windows. The open layout leads to a dining space, accentuated by framed artwork on the walls.
Guest suite in Edgewater
4.91 out of 5 average rating, 538 reviews

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Top guest favorite
A wooden pier extends into the calm waters of Chesapeake Bay, framed by gentle waves and open sky. A grassy area borders the water, with scattered leaves adding to the natural setting. Several boats are visible moored along adjacent docks.
Cottage in North Beach
4.97 out of 5 average rating, 352 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

Popular amenities for Deale vacation rentals

Frequently Asked Questions

  • Do house rentals in Deale have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Deale. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Deale?

    Experience the best of Deale with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Deale have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Deale. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Deale?

    Four-legged friends are welcome in Deale. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Deale have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Deale. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Deale?

    Deale has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Deale?

    Yes! Work meets play with ease at over 20 vacation rentals in Deale featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Deale?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Deale

  • Total vacation rentals

    Explore 30 vacation rentals in Deale

  • Nightly prices starting at

    Deale vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

  • Verified guest reviews

    Over 3,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Deale vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Deale rentals

  • 4.9 Average rating

    Deale stays are highly rated by guests—averaging 4.9 out of 5!

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