Family-friendly holiday rentals in Saint Michaels

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Top-rated family-friendly rentals in Saint Michaels

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Pasadena

4.99 out of 5 average rating, 550 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.

22 Feb – 1 Mar

€ 100 per night

Guest favourite

Home in St Michaels

4.85 out of 5 average rating, 108 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

13–20 Apr

€ 354 per night

Guest favourite

Home in Oxford

4.96 out of 5 average rating, 185 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

19–26 Aug

€ 329 per night

Guest favourite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

16–23 Nov

€ 107 per night

Guest favourite

Flat in Lexington Park

4.97 out of 5 average rating, 511 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

21–28 Feb

€ 122 per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 192 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.

13–20 Sep

€ 146 per night

Guest favourite

Flat in Crownsville

4.98 out of 5 average rating, 165 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

21–28 Oct

€ 105 per night

Guest favourite

Guest house in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

31 Jul – 7 Aug

€ 199 per night

Guest favourite

Home in Cambridge

4.9 out of 5 average rating, 146 reviews

Jewell on the Chesapeake

626 Hills Point on Brannocks Bay off of the Chesapeake Bay is one of the most peaceful beautiful places on the Eastern shore. Our recently renovated 3 bedroom single bath home sits on 3 acres of pristine waterfront with a new 80 ft private dock, with 300 ft of Chesapeake shoreline. The perfect place for kayaking, paddle boarding, fishing, crabbing, boating or just relaxing watching the wildlife.

15–22 May

€ 197 per night

Guest favourite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Summer is a 1-week minimum, Friday-Friday* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300 foot private beach. The year-round property has a pier, in-ground pool (May-October) with amazing river views.

16–23 Oct

€ 771 per night

Guest favourite

Home in Lusby

4.98 out of 5 average rating, 261 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids).

22–29 Sep

€ 182 per night

Superhost

Cottage in Wittman

4.9 out of 5 average rating, 136 reviews

"Wittman Cottage"

Wittman Cottage is located on a beautiful stretch of waterfront views. It is a very nice vacation spot for the family. You can relax and watch the beautiful sunsets from our very large screened porch, or drive to shop and dine in St. Michaels and visit the Maritime Museum which is only 7 miles away..

28 Apr – 5 May

€ 271 per night