Family-friendly vacation rentals in Chestertown

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Top-rated family-friendly rentals in Chestertown

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

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Guest favorite

A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.

Condo in Annapolis

4.94 out of 5 average rating, 390 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

A serene waterfront scene is captured just before twilight, showcasing calm waters reflecting the soft colors of the sky. Distant lights from nearby docks create a gentle glow, framed by the silhouettes of trees and the peaceful harbor setting.

Apartment in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Superhost

A well-lit bathroom features a spacious vanity with dual sinks, complemented by a large mirror above. A glass shower enclosure is present, along with a toilet positioned nearby. The floor showcases a unique blue patterned design, enhancing the overall clean and modern look of the space.

Home in Queenstown

4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Guest favorite

A landscaped yard is displayed, featuring a large tree and seasonal blooming flowers near a stone path. A charming cottage with multiple windows is visible in the background, alongside a bench positioned in a shaded area, providing a serene outdoor setting.

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

A colorful playground is situated under a canopy of trees, featuring a variety of play structures including slides, climbing frames, and swings. The ground is covered in wood chips, creating a safe play environment, while open grassy areas invite outdoor activities.

Place to stay in Annapolis

4.94 out of 5 average rating, 120 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

A living room is showcased with hardwood floors and large windows allowing natural light. A comfortable black chair and a light wood accent chair are present, along with a glass coffee table stacked with books. Decorative elements include a red pouf and indoor plants.

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

A spacious grassy yard is highlighted by a colorful playset, equipped with slides and climbing features. Sunlight filters through surrounding trees, casting gentle shadows on the lawn. The area is open and well-maintained, suitable for outdoor activities and play.

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

A spacious living area showcases a comfortable gray sofa with accent pillows. A wooden dining table is surrounded by upholstered chairs. Large windows allow natural light to flood the room, highlighting framed artwork on the walls and a warm wooden floor.

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

An attic space features a cozy bed with colorful bedding positioned next to a window. Across from the bed, a set of black washers and dryers is situated, with neatly arranged towels and supplies on a shelf above. Warm lighting enhances the inviting atmosphere.

Home in Perryville

4.93 out of 5 average rating, 214 reviews

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Guest favorite

A modern studio loft features an open layout with a cozy leather couch, coffee table, and well-appointed kitchenette. Skylights and large windows offer natural light, while a decorative rug adds warmth to the space. A stylish ceiling fan enhances air circulation.

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.

Top guest favorite

A park scene is visible, featuring a playground with colorful slides and climbing structures framed by several green trees. People are seen enjoying the space, with some pushing strollers on the grassy area. The setting appears to be family-friendly and inviting.

Townhouse in Federal Hill - Montgomery

4.96 out of 5 average rating, 196 reviews

Fed Hill & Inner Harbor / BEST Location & Reviews!

Walk to EVERYTHING! Steps to the Inner Harbor, museums, restaurants, stadiums, & parks. Charm City Circulator & Water Taxi nearby for access to the entire city! Bright home in Historic Federal Hill. Live like a local in an upscale setting! Quiet, comfortable 2 bedroom home perfect for families Preference for booking age to be 25 or older. Baltimore is thriving & evolving, see for yourself how beautiful the area is year round!

Top guest favorite

A bright common room features a comfortable white sofa paired with a glass coffee table. A small wooden table with a floral arrangement is positioned nearby. A map adorns the wall, and a kitchenette area includes a toaster and coffee setup, providing convenience for guests.

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.