Vacation rentals with a pool in Queen Anne&#x27;s County

4.91 out of 5 average rating, 35 reviews

A tranquil saltwater pool is surrounded by lush green grass, featuring a clear blue surface reflecting the sky. Lawn chairs are positioned nearby, with a wooden fence and trees in the background, alongside a house and an American flag gently waving.

Cottage in Chestertown

Chesapeake East Shore Chestertown,Pool (May1),Dock

A bright, airy, refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (your private use 6 hours a day) & dock. Bring your watercraft & gear. Layout is open kitchen, dining and living area. Master & bath on ground; upstairs 2 bedrm suite with bath Fiber optic & smartTVs Gas fireplace, central heat & AC Linens, kitchen utensils & Keurig coffee maker. GE washer and dryer. BBQ, deck chairs, picnic table, seating on water & dock, fire pit

4.94 out of 5 average rating, 94 reviews

A private pool features a clear blue surface, surrounded by a concrete patio. Lush greenery borders the area, while a wooden railing encloses the space. In the background, a barn and a greenhouse complement the serene farm setting.

Farm stay in Centreville

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

Apartment in Stevensville

A spacious backyard features a large in-ground pool surrounded by landscaped gardens. Comfortable seating areas with shaded pergolas are positioned nearby, offering a perfect spot for relaxation. The house stands in the background, complementing the serene outdoor environment.

4.98 out of 5 average rating, 278 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Apartment in Stevensville

An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.

5 out of 5 average rating, 50 reviews

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

4.81 out of 5 average rating, 157 reviews

A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.

Home in Queenstown

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.

Casa particular in Chestertown

An inground pool is surrounded by brick paving, with several lounge chairs positioned nearby. The pool's turquoise water is partially shaded by a large tree, providing a serene outdoor setting. Lush green grass and a wrought-iron fence are visible in the background.

4.92 out of 5 average rating, 148 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

4.95 out of 5 average rating, 96 reviews

A serene view of the Chesapeake Bay is captured from the backyard, featuring a pool surrounded by green lawn. Towering trees provide shade, while a patterned stone patio is visible in the foreground, enhancing the outdoor atmosphere.

Home in Chester

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Cottage in Saint Michaels

4.97 out of 5 average rating, 165 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Guesthouse in Stevensville

4.99 out of 5 average rating, 279 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Home in Queen Anne's County

An aerial view captures a secluded cottage nestled among lush trees, highlighting a heated saltwater pool illuminated softly. The outdoor area features a patio and deck, with warm lighting inviting relaxation in a tranquil setting.

5 out of 5 average rating, 3 reviews

River Heights Retreat (pool and hot tub)

Welcome to this secluded waterfront oasis with a heated salt water pool, hot tub and kayaks! Come and make memories with your family and friends! HIGHLIGHTS POOL HOT TUB BREEO FIREPIT ESPRESSO MACHINE This newly renovated cottage with a pool is located on the banks of a river and has lovely water views from the spacious kitchen and living room, and has a luxurious master suite with a king bed and a bathroom with a double vanity and a luxury tile shower.

4.91 out of 5 average rating, 22 reviews

The exterior of the historic cabin is showcased, featuring a dark blue facade with a white entrance door. Flowerpots flank the entrance, and landscaped gardens present vibrant floral hues. A glimpse of the dock along the river is visible in the background, framed by mature trees.

Cabin in Queenstown

Cozy Historic Cabin on the Water

Step into our almost 300-year-old, historic cabin. This charming cabin, dating back to 1787, is nestled alongside the picturesque Wye River. The views from the dock provide a tranquil setting to unwind and escape the pressures of everyday life. As you step through the door, exposed beams, wooden walls, and modern fireplaces create a cozy atmosphere. Wake up to the melodies of nature and enjoy observing the wildlife in their natural habitat.

5 out of 5 average rating, 3 reviews

A serene outdoor space features a stone-lined swimming pool bordered by lush greenery. The pool is surrounded by trees and flowering plants, creating a tranquil retreat. Sunlight filters through the leaves, adding to the peaceful ambiance of the area.

Home in Queenstown

Pintail Point Cottage

Escape to serene Pintail Point Farm Cottage in Queenstown. Discover 360 degrees of picturesque views. Enjoy boating, paddle boarding, fishing, sporting clays, and scenic waterways. Experience tranquility, outdoor adventures, and water activities at Pintail Point Farm Cottage for an unforgettable getaway. A manager will be on premises at all times.

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Popular amenities for Queen Anne's County rentals with a pool

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Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 38 reviews

The outdoor scene showcases a fenced-in area with a circular above-ground pool adjacent to a wooden deck. Lush green grass surrounds the pool area, with landscaped flower beds and trees in the background, creating a tranquil and spacious environment.

Home in Rock Hall

Rockfish Keeper

Mary JaneRating, 5 stars1 month ago

It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"

5 out of 5 average rating, 15 reviews

A clear swimming pool reflects the overcast sky and surrounding buildings. Multiple white lounge chairs are arranged around the pool, accompanied by blue umbrellas offering shade. The pool area is enclosed by a low fence, creating a serene atmosphere for relaxation.

Home in Rock Hall

The Mariner's House

ErinRating, 5 stars1 month ago

Wonderful property with lots of amenities!

5 out of 5 average rating, 5 reviews

The exterior of the house features a combination of natural stone and shingle siding. A well-maintained garden with flowering shrubs borders the walkway. A small porch is visible, providing access to the entrance, all under a clear blue sky.

Home in Stevensville

Bay Bliss House

IanRating, 5 stars1 week ago

Beautiful property and well maintained. Unique views and plenty to do when the weather is not so good. Great proximity to Annapolis and the Eastern Shore and plenty of great dining spots on the water.

4.89 out of 5 average rating, 53 reviews

A two-story home is seen from the perspective of a patio area, featuring a large saltwater pool in the foreground. Lounge chairs are arranged around the pool, and string lights are hung overhead. A garden area with plants borders the pool, adding greenery to the scene.

Home in Church Hill

Private Peaceful Waterfront House w/ Pool, Hot Tub

LenaRating, 5 stars11 months ago

This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️

4.45 out of 5 average rating, 20 reviews

A private pool is centrally located, surrounded by a well-kept grassy yard. Lounge chairs are positioned around the pool, providing relaxation options. The two-story cottage is visible in the background, along with a shaded area and trees that create a serene setting.

Home in Stevensville

Private Pool, Bay Views near Kentmorr Bar & Beach

DeniseRating, 5 stars11 months ago

Had a wonderful time with my family

4.58 out of 5 average rating, 12 reviews

The home features a welcoming exterior illuminated by warm outdoor lighting, showcasing large windows and a spacious deck with comfortable seating. A pool and spa, glistening in green hues, are surrounded by lush landscaping, creating a serene evening atmosphere.

Home in Saint Michaels

10 Minutes to St. Michaels with a Private Pool

SarahRating, 5 stars1 week ago

This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!

5 out of 5 average rating, 17 reviews

The outdoor pool area features a spacious salt-water pool surrounded by a stone patio. Comfortable seating is arranged on either side, with colorful landscape visible in the background and an umbrella providing shade. The skyline is adorned with hues of sunset across the bay.

Home in Stevensville

Bayside Escape

JohnRating, 5 stars5 days ago

Our family of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors