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House holiday rentals in Kent County

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Top-rated house rentals in Kent County

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Guest favourite
A wooden pier extends from the sandy shore towards a home surrounded by tall trees, with warm light glowing from large windows. The sky displays soft pink and blue hues as the day transitions to evening.
Home in Chestertown

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

4.91 out of 5 average rating, 66 reviews
Top guest favourite
The single-story ranch home is set on a spacious lot adorned with a mix of grass and fallen leaves. Blue shutters frame the windows, and a welcoming front porch is furnished with several chairs. A two-car garage is visible to the left.
Home in Rock Hall

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

4.98 out of 5 average rating, 110 reviews
Top guest favourite
An updated kitchen features modern appliances, including a white refrigerator and a built-in stove. Light grey cabinetry is complemented by a spacious countertop with a subtle marble pattern. Shelves display decorative items, while a wall art piece adds a touch of color.
Home in Chestertown

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

4.96 out of 5 average rating, 75 reviews
Top guest favourite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

4.97 out of 5 average rating, 131 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.

4.98 out of 5 average rating, 194 reviews
Top guest favourite
A charming white house with a steep roof and black shutters is displayed. The front porch features columns and seating areas, with potted plants lining the edges. An American flag hangs from the porch. Lush greenery surrounds the property, enhancing its inviting exterior.
Home in Chestertown

The Patriot House-Chestertown, MD

Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.

4.96 out of 5 average rating, 135 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

4.96 out of 5 average rating, 118 reviews
Top guest favourite
The front porch features sheer white curtains draped along the railing, creating an airy atmosphere. A bright yellow door serves as a focal point, flanked by large windows above. Brick steps lead up to the entry, surrounded by neatly arranged greenery.
Home in Rock Hall

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

4.99 out of 5 average rating, 130 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!

4.96 out of 5 average rating, 105 reviews
Top guest favourite
Home in Centreville

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.

5.0 out of 5 average rating, 62 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.

5.0 out of 5 average rating, 252 reviews
Top guest favourite
A bright living space is characterized by light blue walls and hardwood flooring. A brown recliner and a wooden coffee table are present, along with a turquoise entertainment unit housing a television. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.
Home in Chestertown

2 Beds, 2.5 Baths - Perfect Downtown Location

Charming and inviting, this beautifully updated home in historic Chestertown offers the perfect blend of comfort and location. Featuring 2 bedrooms—each with its own en suite bath—plus an additional half bath on the first floor, it comfortably accommodates up to 4 adults. Enjoy bright, thoughtfully designed living spaces throughout. Just a few blocks from downtown shops, restaurants, and waterfront, and an easy walk to Washington College.

4.98 out of 5 average rating, 126 reviews

Popular amenities for house rentals in Kent County

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
The outdoor area features an in-ground pool, accompanied by several sun lounge chairs arranged along the stone patio. Lush greenery surrounds the pool, contributing to a relaxing atmosphere. A staircase leads up to the home, offering easy access between the spaces.
Home in Worton

Cording Lodge*Pool*Pickleball/Basketball court

4.93 out of 5 average rating, 30 reviews
Guest favourite
Home in Chestertown

Waterfront Wellness - *With Pool and Hot Tub!*

4.9 out of 5 average rating, 30 reviews
Guest favourite
Home in Millington

The Peaceful Getaway (with private pool & hot tub)

4.89 out of 5 average rating, 89 reviews
Guest favourite
Home in Queen Anne's County

River Heights Retreat (hot tub and luxury)

4.89 out of 5 average rating, 35 reviews
Superhost
A rectangular swimming pool is situated in an open area surrounded by grass, offering a view of the expansive landscape. Two lounge chairs with umbrellas are positioned beside the pool, enhancing the outdoor relaxation space under a partly cloudy sky.
Home in Centreville

Creek Cottage at Reed Creek | an ESVR property

5.0 out of 5 average rating, 6 reviews
Top guest favourite
A group of seated individuals enjoys a view of the Chester River, surrounded by lush green grass. Comfortable lounge chairs are arranged in a line, facing the water. The scene is framed by trees, with a cloudy sky overhead, creating a peaceful atmosphere.
Home in Chestertown

Chestertown Watson Family Farm

4.98 out of 5 average rating, 42 reviews
Home in Church Hill

Pool + Hot Tub + Pickleball | Waterfront

4.83 out of 5 average rating, 72 reviews
Guest favourite
An outdoor area features a private pool surrounded by a deck with lounge chairs and an umbrella. A grassy area leads to a waterfront view, showcasing boats at the marina and a gentle breeze rustling the trees.
Home in Rock Hall

Waterfront w/pier, Hot Tub, pool, and in town

4.84 out of 5 average rating, 25 reviews

Weekly house rentals

Top guest favourite
The front of a colonial-style house features a yellow facade with dark green shutters, framed by lush trees and vibrant garden plants. A white picket fence lines the yard, leading to the entrance with a red front door and stone steps surrounded by flowers.
Home in Chestertown

Magnolia House is for sale! Historic Chestertown

5.0 out of 5 average rating, 61 reviews
Top guest favourite
Adirondack chairs are arranged around a fire pit on a grassy riverside. A vibrant sunset casts pink and orange hues across the sky and reflects on the calm water, creating a serene outdoor atmosphere. A tree stands nearby, adding to the peaceful setting.
Home in Chestertown

Down by the River

4.97 out of 5 average rating, 63 reviews
Top guest favourite
Home in Worton

Cozy Cape Cod in worton MD

5.0 out of 5 average rating, 24 reviews
Top guest favourite
A bright living space is highlighted by a wall of large windows showcasing views of water and greenery outside. A modern gray sofa is paired with decorative pillows, and a small coffee table rests on a textured rug. Natural light fills the room, creating an inviting atmosphere.
Home in Rock Hall

Water Views in Rock Hall

5.0 out of 5 average rating, 71 reviews
Guest favourite
An outdoor fire pit is surrounded by six wooden lounge chairs, arranged on a gravel patio. Lush green grass and trees provide a natural backdrop, while tranquil river views are visible beyond the fire pit, reflecting the soft colors of the sky.
Home in Millington

Anchors Away

4.95 out of 5 average rating, 44 reviews
Top guest favourite
A charming two-story house with a white exterior is framed by lush greenery. The front porch features a welcoming entrance with steps leading to the door. Large windows are adorned with dark shutters, and vibrant flower pots add a touch of color to the landscape.
Home in Rock Hall

Charming Cape By The Bay!

4.95 out of 5 average rating, 91 reviews
Top guest favourite
The screened-in deck features a comfortable seating arrangement with two armchairs and a sofa, all surrounding a central coffee table. A large, decorative plant adds a touch of nature, while panoramic views of the surrounding greenery are visible through the screens.
Home in Galena

Connection Pointe•River views•Quiet•Peaceful

4.96 out of 5 average rating, 78 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

4.99 out of 5 average rating, 73 reviews

Private house rentals

Top guest favourite
Adirondack chairs are positioned on a grassy area overlooking the Chesapeake Bay. A small side table accompanies the chairs, providing a space for drinks or snacks. Trees provide shade to this serene outdoor spot, where the blue water and sky blend harmoniously.
Home in Earleville

Sweet Bay Overlook

5.0 out of 5 average rating, 50 reviews
Guest favourite
A spacious outdoor deck is shown, featuring a wooden dining table and four Adirondack chairs. The serene waterfront view overlooks the Chesapeake Bay, with lush greenery extending towards the horizon. A BBQ grill is positioned nearby, complementing the relaxed atmosphere.
Home in Rock Hall

Relaxation by the Bay!

4.86 out of 5 average rating, 21 reviews
Guest favourite
A bright sunroom features large windows that allow natural light to fill the space. Comfortable seating includes a vibrant pink sofa and two green chairs beside a small accent table. A soft area rug lays on the floor, enhancing the cozy atmosphere.
Home in Chestertown

In Town Chestertown Rancher (1 Block to College)

4.98 out of 5 average rating, 59 reviews
Top guest favourite
The exterior features a welcoming entrance with a wooden deck, adorned with turquoise chairs for relaxation. Lush greenery and blooming flowers enhance the vibrant atmosphere. The entrance is framed by a mix of brick and light-colored siding, providing a charming and friendly appearance.
Home in Rock Hall

The Bay House - just a few steps to the bay!

4.98 out of 5 average rating, 54 reviews
Top guest favourite
A tranquil beach scene captures a vibrant sunset over the water. A sailboat glides smoothly in the distance while the shoreline is lined with smooth rocks and sandy areas. Soft waves lap against the shore, creating a serene atmosphere.
Home in Rock Hall

Oyster Cove - Walk to Marinas

5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Rock Hall

1 Particular Harbor – Single Story Coastal Home

5.0 out of 5 average rating, 48 reviews
Top guest favourite
A well-lit living area features comfortable seating on a soft gray sofa, complemented by a wooden coffee table and a television mounted on the wall. A ceiling fan is present above, and natural light filters in through large windows, creating an inviting space.
Home in Stevensville

Screened Porch | Near Bay Bridge & USNA | Big Yard

4.98 out of 5 average rating, 53 reviews
Guest favourite
A charming two-story cottage is framed by tall trees and a grassy yard. The light siding contrasts with the darker roof, while the front steps lead to a welcoming door. Clouds fill the sky, and the surrounding greenery complements the tranquil setting.
Home in Galena

Hunter's Lodge

4.85 out of 5 average rating, 13 reviews

Destinations to explore