Family-friendly vacation rentals in Tilghman Island

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Top-rated family-friendly rentals in Tilghman Island

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

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Guest favorite

Condo in Annapolis

4.94 out of 5 average rating, 388 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens, lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 10.

Guest favorite

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

Cottage in Rock Hall

4.99 out of 5 average rating, 108 reviews

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Top guest favorite

Place to stay in Annapolis

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Top guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 221 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.

Guest favorite

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Superhost

Home in Annapolis

4.85 out of 5 average rating, 221 reviews

Spacious Home in Private Neighborhood with Beach

A beautiful and spacious home located on the Severn River in the gated community of Epping Forest! The house is just 7 miles from downtown Annapolis and offers guests a private, secluded home away from home. A private beach and club house are located within walking distance! Enjoy a fire on either of the two levels of private decks, or gather around the large dining room table for any of the provided board games. An abundance of amenities will make your stay more than comfortable!

Guest favorite

Apartment in Deale

4.91 out of 5 average rating, 620 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 favorite

Cottage in Colonial Beach

4.93 out of 5 average rating, 168 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Superhost

Townhouse in Capitol Hill

4.85 out of 5 average rating, 377 reviews

MODERN HOME NEAR CAPITOL HILL ✩✩✩✩✩ Walk to METRO subway

♢ 2 blocks to the nearest Metro subway station ♢ 8-minutes by car to downtown Washington DC ♢ HDTV + Roku TV in living room & Master bedroom ♢ Amazon's Alexa at your service on the Echo ♢ High-speed Wi-Fi ♢ Kid- and family-friendly rental Relax in style in this lovely DC home, located just minutes from Capitol Hill and the must-see H St. Corridor in the Hill East community, and just a short metro ride from the museums.

Top guest favorite

Home in Lusby

4.99 out of 5 average rating, 294 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). No pets allowed.

Top guest favorite

Guest suite in Annapolis

4.95 out of 5 average rating, 192 reviews

Cozy Naptown Perch

Perfectly Placed Perch in Murray Hill neighborhood. 1 mile to USNA stadium; 1 mile to historic downtown. Walk to local restaurants, in town events. Few blocks to water access. 2 bedroom upstairs suite recently renovated. Common room has sofa, table and chairs, coffee/ tea set up. Patio, fire pit available to guests.

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What guests are saying

Osprey's roost: Spring and summer 2025

4.97 out of 5 average rating, 159 reviews6 days ago

We had such a wonderful stay at this home! I visited with my three young kids and there was never a dull moment—so many fun activities to do, both indoors and out. We loved having access to the kayak and canoe, which we used on both the ocean and the nearby lake. The location was peaceful and quiet, perfect for relaxing, and we had a blast fishing right off the dock. Inside, the house was cozy, spotless, and very comfortable. The beds were clean and comfy, and the kitchen was fully stocked with everything we needed—including spices and condiments, which made cooking easy. There were also tons of games to keep the kids entertained during downtime. The hosts were incredibly friendly, responsive, and proactively helpful, checking in by text and making sure we had everything we needed. I highly recommend this place and would absolutely come back!

Home in Hague

What guests are saying

Hawthorn Cottage Great In-town Location!

4.96 out of 5 average rating, 101 reviews8 months ago

We were 4 adults and 1 child (9y). We absolutely loved our stay at Jackie’s place. She was proactive in her communication and very flexible. She was able to offer as an extra night for free. We understand that this will not always be possible but it isn’t the norm nowadays anymore and it shows she goes above and beyond for her customers. The house was close to the beach, clean and everything was just as described online. We loved the quiet area, perfect for families with children or people who don’t like overcrowded beaches. Our boy loved catching jelly fish, collecting rocks and shells and of course being in the water. Our favorite restaurant was high tides (yummy cocktails and the best fish and chips basket). We also ventured out to see James Monroe’s and George Washington’s birthplace which were only a 20 minutes drive away and really worth a visit. Jackie, thank you for everything!

Cottage in Colonial Beach

What guests are saying

1 block to metro-Capitol Hill Garden flat

4.93 out of 5 average rating, 459 reviews2 weeks ago

Every aspect of this trip was amazing and it started with crystal effectively communicating before we even left home. From recommendations to using the metro, she had us covered. The location could not be more perfect in regards to getting to the Capital, monuments and great resteraunts. The neighborhood felt safe and walking around was truly a pleasure. The accommodations were lovely and very comfortable. Everything was clean and easy to use, and very we thought out. Loved it!

Guest suite in Capitol Hill

What guests are saying

DC PRIME SPOT - Walk to Metro & Monuments+ Parking

4.91 out of 5 average rating, 199 reviews1 week ago

I had a great experience staying at Robin’s place on a solo trip to DC. The apartment was exactly as described and the location was great. Easy walk to the metro and tons of restaurants nearby. Trader Joe’s is close by as are other shops. Would definitely stay again.

Apartment in Capitol Hill

What guests are saying

Historic Capitol Hill, Best Location! 3 Bed/3 Bath

4.84 out of 5 average rating, 100 reviews2 weeks ago

What a convenient location! We were 4 adults and 2 young children. We ate most meals on Barracks Row - lots of restaurants- many child-friendly. Easy walk to the Metro with frequent trains to various DC locations. The house is, as listed, older and has lots of charm. When we encountered any minor problems, hosts were quick to respond. We would stay there again.

Townhouse in Capitol Hill

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