Vacation rentals with a pool in Queen Anne's County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Queen Anne's County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

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

4.91 out of 5 average rating, 35 reviews

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

Guest favorite

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

4.94 out of 5 average rating, 94 reviews

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

Top guest favorite

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.

Apartment in Stevensville

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.

Top guest favorite

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.

Apartment in Stevensville

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.

Superhost

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

4.81 out of 5 average rating, 157 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.

Top guest favorite

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.

Casa particular in Chestertown

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!

Guest favorite

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

4.95 out of 5 average rating, 96 reviews

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.

Guest favorite

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.

Top guest favorite

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.

Superhost

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.

Home in Queen Anne's County

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.

Superhost

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

4.91 out of 5 average rating, 22 reviews

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.

Superhost

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

5 out of 5 average rating, 3 reviews

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.