Holiday rentals in Kennedyville

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Top-rated holiday rentals in Kennedyville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A historic two-story house is nestled among lush greenery, featuring a muted grey exterior with bright red shutters. The inviting front porch is framed by trees, contributing to the home's serene and picturesque setting.

Guest suite in Chestertown

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

ValueLocationComfort

4.99 out of 5 average rating, 151 reviews

Top guest favourite

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

FamilyValueSleep quality

4.98 out of 5 average rating, 199 reviews

Top guest favourite

Guest suite in Chestertown

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate a portion of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

LocationValueSleep quality

4.99 out of 5 average rating, 258 reviews

Guest favourite

A hot tub bubbles gently in the foreground, surrounded by lush greenery and a view of the waterfront. Twinkling string lights hang above the screened porch, which features a spacious dining area. The sunset casts a warm glow over the scenic landscape.

Home in Chestertown

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

ValueFamilyCheckout

4.95 out of 5 average rating, 122 reviews

Top guest favourite

Home in Chestertown

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located. Complimentary on-street parking.

ValueFamilyAccuracy

4.97 out of 5 average rating, 107 reviews

Top guest favourite

The two-story cottage is framed by vibrant orange daylilies, with a welcoming porch adorned with patriotic bunting. An American flag hangs prominently, while the well-maintained landscape invites guests to relax. The exterior features a mix of siding and a metal roof.

Home in Betterton

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage is in the center of Betterton. There's a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom (on the first floor) and an amazing outdoor shower available seasonally! There are three bedrooms (all on the second floor). Enjoy Betterton Beach which is down the street! Look for sea glass or watch the sunset! There is a cute park with a playground in town that the kids love! It also has pickleball, tennis and basketball courts.

LocationFamilyParks

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Flat in Chestertown

Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

LocationFamilyCondition

4.98 out of 5 average rating, 146 reviews

Top guest favourite

The charming cottage features a covered front porch with a white railing and a decorative door, framed by lush greenery and blooming hydrangeas. A flag is displayed proudly, while stairs lead up to the welcoming entrance. Natural light brightens the overall exterior.

Cottage in Betterton

Charming Home w/Great Porch

We would love to share our well-loved cottage on the Bay with you. Most loved for its beautiful views and quiet town, it is a perfect place to relax with great beach access. We think you'll love it too. Plenty of space to spread out and comfy spaces to enjoy together: whether on the screened porch (our favorite), in the updated foodie-kitchen, or swinging on the swing, snoozing in hammock or walking to the beach - you will be glad you found this place-we definitely are!

FamilyLocationParks

5.0 out of 5 average rating, 45 reviews

Superhost

A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.

Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

FamilyValueWifi

4.89 out of 5 average rating, 122 reviews

Guest favourite

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

LocationValueWifi

4.96 out of 5 average rating, 107 reviews

Top guest favourite

Home in Lynch

Bamboo Sands Beach Getaway

Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub.... Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on a sandy area of the Chesapeake Bay where families can RELAX & reconnect. Here, serenity and fun flow as easily as the coastal breeze. Enjoy sandy beaches without the crowds, the sounds of waves on the bay without the oceanfront price tag, a coastal luxury getaway...

FamilyLocationSleep quality

4.97 out of 5 average rating, 31 reviews

Top guest favourite

Home in Chestertown

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 258 reviews