Vacation rentals in Pooles Island

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Top-rated vacation rentals in Pooles Island

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Top guest favorite

A spacious lounge area features comfortable seating with a sectional sofa and two dark leather sofas. A modern coffee table sits atop an area rug, and a wall-mounted smart TV is visible. Natural light enters through several windows, contributing to the inviting atmosphere.

Guest suite in Joppatowne

4.99 out of 5 average rating, 171 reviews

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe & dresser. Washer/dryer available upon request. Please review house rules before booking

Top guest favorite

The image features a spacious outdoor area with a hot tub and a relaxing seating arrangement. Views of the waterfront are visible in the background, framed by lush green trees. A blue hammock is draped nearby, and a basket of towels rests on a small table.

Home in Middle River

5 out of 5 average rating, 27 reviews

Waterfront Paradise on Seneca Creek w/Hot Tub

Welcome to this luxurious waterfront home on Seneca creek with breathtaking views and amazing sunsets! This home features 4 bedrooms and 4 full bathrooms with water views from just about every room in the house. Plenty of outdoor space for relaxing, sitting by the firepit, chilling out in the hammocks, soaking in the hot tub, frolicking in the water or fishing from the private pier. This home is convenient to many activities, but you may never want to leave as it’s a destination all on its own.

Guest favorite

A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.

Apartment in Dundalk

4.96 out of 5 average rating, 25 reviews

Waterfront Romantic Studio

Unwind at our private studio getaway-featuring an updated kitchen & bathroom, and cozy sleeping area. Separate entrance for complete privacy. Step out onto the shared deck and take in stunning water views, perfect for your morning coffee or a relaxing evening drink enjoy the waterfront vibe. Make memories around the fire pit or explore nearby state parks with scenic hiking trails and beaches. Whether you’re here for a show, a convention, or just some sightseeing, only 20 minutes from Baltimore.

Guest favorite

A sunroom features a yellow door leading outside, with a comfortable seating area adorned with floral patterns and yellow cushions. Lush greenery hangs from the ceiling and sits on various surfaces, creating a vibrant and fresh environment, illuminated by natural light from the nearby windows.

Home in Baltimore

4.95 out of 5 average rating, 198 reviews

RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

Top guest favorite

A charming cottage with a yellow exterior is framed by lush greenery. A wooden porch features two classic white rocking chairs, inviting relaxation. The front entrance is highlighted by large glass doors and a wide set of steps leading to the well-manicured lawn.

Cottage in Rock Hall

4.96 out of 5 average rating, 163 reviews

The Blissful Retreat @theblissfulretreat

Serene space nestled in the woods; with water views. You have your own private cottage on our 10 acre property to watch the sunsets and enjoy the nature all around. You'll spot deer, bunnies, frogs, turtles, birds and so much more from the lovely front porch! As a Nurse I can guarantee our space has always been cleaned and sanitized to the highest standards, regular use of a ozone light. Check us out on insta for more blissfulness - theblissfulretreat and FB- theblissfulretreatrockhall

Top guest favorite

A calm body of water reflects clear blue skies and wispy clouds, with faint sunbeams glimmering across the surface. A wooden dock stretches into the water, framed by trees and distant houses along the shoreline, providing a serene waterfront atmosphere.

Cabin in Middle River

5 out of 5 average rating, 42 reviews

Cozy Waterfront Cabin Escape

Want to escape the city for a night or week and spend time sitting by the water reflecting and taking it all in, this is the cabin for you. Two (2) bedroom, 1.5 bath shore cabin (600 sqft) that provides the perfect balance of indoor charm with outdoor access and enjoyment. Bring your kayaks and launch them from the dock and explore beautiful Seneca Creek or just sit and relax in the hot tub. High-speed internet makes this a great working location as well with raise/lower desk and 2nd monitor.

Top guest favorite

A cozy studio features a full-size bed with light bedding, complemented by a world map artwork on the wall. A seating area includes a chair and small table. Large windows allow natural light to fill the room, enhancing the welcoming atmosphere.

Apartment in Rock Hall

5 out of 5 average rating, 100 reviews

Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in the Cinnamon By The Bay Inn. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

Guest favorite

A houseboat is docked at a marina, featuring a spacious upper deck under a blue canopy. The exterior showcases large windows and a white hull, surrounded by green trees. A wooden dock extends in front, offering easy access to the boat.

Houseboat in Essex

5 out of 5 average rating, 9 reviews

Lovin’ Life | Floating Getaway on Sue Creek

Escape the ordinary & fall in love with life on the water aboard “Lovin’ Life”—a cozy, romantic retreat on our beautifully maintained 2003 Gibson Classic, a unique blend of houseboat & cabin cruiser. Docked on peaceful Sue Creek, this floating hideaway offers a memorable stay filled with relaxation, waterfront views, & fun! Houseboat Charm • Outdoor Fun • Waterfront Dining Steps Away! On-site Charley’s Waterfront Restaurant with indoor & outdoor dining + plenty of TVs for sports fans!

Guest favorite

The exterior view showcases a modern home surrounded by lush, green landscaping. The spacious yard features a combination of trees and open grassy areas, providing a serene setting. The house features multiple windows and a large porch, inviting relaxation and enjoyment of the tranquil surroundings.

Home in Chestertown

4.97 out of 5 average rating, 32 reviews

Lotus House: spacious, private, expansive views

Relax and spread out in this modern yet perfectly appointed Eastern Shore Home. Neighboring the Chesapeake Bay and situated on a quiet and private road, you will be surrounded by preserved farmland and woods. Peer through the trees for a partial water view and fabulous sunsets. Fresh steamed crabs and other local seafoods are available for pick up just 2 miles away. Or try out the waterfront restaurant, beach bar, or rent a boat slip at Great Oak Landing Marina just a mile away.

Guest favorite

A wooden dock extends into a calm river, featuring three red Adirondack chairs at the end. Surrounded by trees, the still water reflects the overcast sky, providing a serene outdoor space for relaxation.

Home in Chestertown

4.98 out of 5 average rating, 60 reviews

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

Top guest favorite

A wraparound deck features bright turquoise Adirondack chairs and a matching side table, positioned near a railing. Sea views extend to the horizon, with gentle waves lapping against the distant rocks. A green potted plant adds a splash of color to the serene setting.

Home in Sparrows Point

5 out of 5 average rating, 72 reviews

Pristine Waterfront Home with Bay Views for Miles

Welcome to our home on the Chesapeake Bay! This freshly renovated 3 BR, 2 1/2 BA home sits directly at the water's edge, nestled toward the end of a quiet street. This house is 20 minutes east of Baltimore, yet you’ll feel like you’ve entered a different world. Take in the many sights and sounds of the bay from our huge wraparound deck or explore the bay by kayak. Inside, you’ll love the comfortable yet stylish living spaces, serene bedrooms, and luxurious baths.

Guest favorite

Large windows offer unobstructed views of Chesapeake Bay, allowing natural light to fill the space. A spacious seating area with a light-colored sofa is visible, alongside a dining table that accommodates multiple chairs. The outdoor deck can be seen through the doors, extending towards the water.

Home in Rock Hall

4.88 out of 5 average rating, 17 reviews

Chesapeake Bay Retreat W/Breathtaking Views

Escape to serenity on the shores of Chesapeake Bay! This luxurious, multimillion-dollar waterfront retreat offers sweeping water views, upscale furnishings, and timeless historic charm. Minutes from vibrant Rock Hall and Chestertown. Relax on the deck with morning coffee, stroll or bike the scenic waterfront paths, enjoy sun dips at Ferry Park beach, catch live performances at The Mainstay, or explore birdwatching trails at Eastern Neck Wildlife Refuge.