Family-friendly vacation rentals in Chestertown

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chestertown

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

0 of 0 items showing

1 of 3 pages

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.

Dec. 6 – 13

$145 CAD per night

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 566 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!

May 21 – 28

$307 CAD per night

Guest favourite

Home in Glen Burnie

4.97 out of 5 average rating, 396 reviews

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

Sep. 27 – Oct. 4

$201 CAD per night

Guest favourite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Nov. 26 – Dec. 3

$468 CAD per night

Guest favourite

Cottage in Rock Hall

4.99 out of 5 average rating, 102 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!

Feb. 16 – 23

$340 CAD per night

Guest favourite

Guest suite in Baltimore

4.91 out of 5 average rating, 584 reviews

Secret Garden in the City

Art is everywhere! Most walkable part of Bmore! We are hosts with the inside scoop on the city. Close to everything! 25 minutes to airport (~$35 Lyft/Uber) 15 minute walk to InnerHarbor and 10 minute walk to many restaurants, bars, and boutiques. To get to the: National Aquarium/Inner Harbor (main tourist attraction) 0.6 miles, Marriott Waterfront Hotel/Conference Center 0.5 miles, Johns Hopkins Main Hospital 1.2 miles, Baltimore Convention Center 1.3 miles, and 2.6 miles to Penn Station.

Aug. 16 – 23

$179 CAD per night

Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 104 reviews

Waterfront w/Pier &Walking Distance to Chestertown

This 4 bedroom, 3 bath waterfront home is a terrific place to enjoy time with family and friends. This home has amazing amenities; from the stylish updated renovations and furnishings (some antiques), the screened porch, patio, fire pit, hot tub (Oct - April), sporting equipment, to the spacious, comfortable, indoor & outdoor gathering spaces. The kitchen is well-appointed with gourmet appliances, and plenty of hosting and culinary supplies to savor wonderful meals together at the house.

Nov. 9 – 16

$695 CAD 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.

Sep. 13 – 20

$213 CAD per night

Guest favourite

Apartment in Crownsville

4.98 out of 5 average rating, 164 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.

Jun. 28 – Jul. 5

$200 CAD per night

Guest favourite

Guest suite in Edgewater

4.89 out of 5 average rating, 437 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.

Jun. 11 – 18

$153 CAD per night

Guest favourite

Guesthouse in Havre de Grace

4.89 out of 5 average rating, 223 reviews

Studio apartment with off street parking

Private studio apartment just minutes away from the mouth of the Chesapeake Bay. Visiting our small town of Havre de Grace for a wedding or a local event, choose to relax in our sports themed comfortable home away from home. Havre de Grace has a lot of wonderful events, shops and restaurants to offer, and you will be just steps away from them.

Dec. 10 – 17

$158 CAD per night

Guest favourite

Guest suite in Arnold

4.85 out of 5 average rating, 497 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

Clean, bright, private and spacious guest suite, downstairs in my home. The space is a living room, bedroom and bath. Separate entrance, complete privacy and isolation. The bedroom is dark and quiet. Disinfected and safe. Both rooms have a separate access to the bathroom. There is a lovely, lush view out the back. Self check-in.

Aug. 13 – 20

$180 CAD per night