Family-friendly holiday rentals in Saint Michaels

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Top-rated family-friendly rentals in Saint Michaels

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Guest favourite

Apartment in Pasadena

4.99 out of 5 average rating, 548 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.

6–13 Dec

$178 NZD per night

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 567 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!

3–10 Jul

$211 NZD per night

Guest favourite

Home in St Michaels

4.85 out of 5 average rating, 107 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.

5–12 Feb

$632 NZD per night

Guest favourite

Home in Oxford

4.96 out of 5 average rating, 184 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.

21–28 Oct

$550 NZD 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.

10–17 Nov

$190 NZD per night

Guest favourite

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.

13–20 Sep

$260 NZD per night

Guest favourite

Apartment 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.

28 Jun – 5 Jul

$247 NZD per night

Guest favourite

Guesthouse 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!

15–22 Oct

$356 NZD per night

Guest favourite

Guesthouse in Highland

4.98 out of 5 average rating, 264 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

2–9 Oct

$218 NZD per night

Guest favourite

Tiny home in Bethesda

4.96 out of 5 average rating, 322 reviews

Middleton Cottage, near NIH; Free Parking Permit

Our newly updated charming guest cottage is nestled on a tree-lined residential street in the heart of Bethesda, just two blocks from the Bethesda Metro stop. A vast array of restaurants, clubs, shops, farmer's markets, bike trails, theaters, galleries, parks and more are a quick walk from our front gate. Guests enjoy relaxing in the backyard (which is shared with residents of the main house) and dinning on the patio. Self check-in is easy with a keypad.

21–28 Aug

$236 NZD per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

810 Seabreeze Rd is a quiet cozy retreat located on Brooks Creek off the little Choptank river directly across from the ragged point county boat ramp and dock. Guests are welcome to bring their boat. The house's private dock is just a quarter mile from the public marina. This house is the perfect place for boating, kayaking, paddle boarding, fishing, swimming, crabbing or just relaxing watching the sunset over the historic little Choptank river.

8–15 Oct

$287 NZD 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.

25 Jun – 2 Jul

$1,620 NZD per night