Family-friendly holiday rentals in Tilghman Island

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Top-rated family-friendly rentals in Tilghman Island

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Guest favourite

Serviced apartment in Pasadena

4.99 out of 5 average rating, 554 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.

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 570 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!

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.

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.

Guest favourite

Flat in Crownsville

4.98 out of 5 average rating, 166 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.

Guest favourite

Guest house in Galesville

4.95 out of 5 average rating, 164 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!

Guest favourite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 105 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Guest favourite

Flat in Deale

4.91 out of 5 average rating, 614 reviews

Romantic Wtrfrnt Flat+Solarium@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 TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

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.

Guest favourite

Home in Lusby

5.0 out of 5 average rating, 112 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*One summer week left, June 21-28* 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, and in-ground pool (May-October) with amazing river views.

Guest favourite

Guest suite in Edgewater

4.89 out of 5 average rating, 441 reviews

South River Park Apartment

Located minutes from Annapolis, MD 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.

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. Michael's and visit the Maritime Museum which is only 7 miles away..

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Tilghman Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Kent Narrows

5.0 out of 5 average rating, 280 reviews

Chester Riverfront At Kent Narrows

Guest favourite

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

Guest favourite

Townhouse in Baltimore

4.95 out of 5 average rating, 574 reviews

Romantic Hot Tub Getaway, Walk to Fells Point

Superhost

Home in Edgewater

4.76 out of 5 average rating, 270 reviews

Edgewater/Mayo Getaway!

Guest favourite

Home in Montross

4.95 out of 5 average rating, 220 reviews

Stunning Lake House Retreat on the Potomac River

Guest favourite

Flat in Arnold

4.96 out of 5 average rating, 158 reviews

Celebrate Summer By Your Private Pool

Guest favourite

Home in Harwood

4.94 out of 5 average rating, 118 reviews

Luxury Home, Sleeps 15, Private Pool, Close to DC

Guest favourite

Home in Arlington

4.86 out of 5 average rating, 267 reviews

Arlington farmhouse w/easy access to everything DC

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Family- and pet-friendly home rentals

Guest favourite

Cabin in Gambrills

4.89 out of 5 average rating, 141 reviews

Relaxing Cabin Get Away Near Annapolis & DC

Guest favourite

Flat in Edgewater

4.92 out of 5 average rating, 402 reviews

Pet Friendly Garden Apartment Near Annapolis

Guest favourite

Flat in Solomons

4.99 out of 5 average rating, 226 reviews

Island Breeze Solomons

Guest favourite

Flat in Silver Spring

4.93 out of 5 average rating, 395 reviews

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Guest favourite

Guest suite in Arnold

4.85 out of 5 average rating, 504 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 193 reviews

Beautiful Waterfront Chestertown Getaway

Guest favourite

Cottage in Deale

4.89 out of 5 average rating, 149 reviews

Rockhold Creek Cottage

Guest favourite

Flat in Lexington Park

4.97 out of 5 average rating, 513 reviews

Historic St. Mary's City, MD

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Family-friendly home rentals with a pool

Guest favourite

Guest house in Highland

4.98 out of 5 average rating, 265 reviews

Woodland Retreat

Guest favourite

Guest suite in Catonsville

4.94 out of 5 average rating, 470 reviews

Rollingside: Two-Room Guest Suite

Superhost

Home in Queenstown

4.81 out of 5 average rating, 143 reviews

Bay Breeze Retreat

Guest favourite

Apartment in Oxon Hill

4.88 out of 5 average rating, 132 reviews

Modern Apartments available at National Harbor

Superhost

Cottage in Neavitt

4.88 out of 5 average rating, 17 reviews

Grandview Cottage #2 -A special peaceful place!

Guest favourite

Cabin in Saint Michaels

4.99 out of 5 average rating, 97 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

Guest favourite

Home in Saint Michaels

4.98 out of 5 average rating, 84 reviews

SM’s Premier Rental Heated Pool opens 4/12

Guest favourite

Villa in Easton

4.95 out of 5 average rating, 38 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

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Quick stats about holiday rentals that are family-friendly in Tilghman Island

Total rentals
10 properties
Local attractions
Wylder Hotel Tilghman Island, Characters Bridge Restaurant and Two if by Sea
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
200 reviews
Nightly prices starting at
$203 SGD before taxes and fees

Family-friendly holiday rentals in Tilghman Island

Top-rated family-friendly rentals in Tilghman Island

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Tilghman Island family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Kent Narrows

Home in Deale

Townhouse in Baltimore

Home in Edgewater

Home in Montross

Flat in Arnold

Home in Harwood

Home in Arlington

Family- and pet-friendly home rentals

Cabin in Gambrills

Flat in Edgewater

Flat in Solomons

Flat in Silver Spring

Guest suite in Arnold

Guest suite in Chestertown

Cottage in Deale

Flat in Lexington Park

Family-friendly home rentals with a pool

Guest house in Highland

Guest suite in Catonsville

Home in Queenstown

Apartment in Oxon Hill

Cottage in Neavitt

Cabin in Saint Michaels

Home in Saint Michaels

Villa in Easton

Quick stats about holiday rentals that are family-friendly in Tilghman Island

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore