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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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Cottage in Chestertown

4.91 out of 5 average rating, 34 reviews

Chesapeake East Shore Chestertown, Pool & 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

Farm stay in Centreville

4.94 out of 5 average rating, 79 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

Rental unit in Stevensville

4.98 out of 5 average rating, 273 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.

Rental unit in Stevensville

5 out of 5 average rating, 35 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.

Home in Stevensville

5 out of 5 average rating, 124 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Home in Stevensville

4.98 out of 5 average rating, 86 reviews

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.

Home in Queenstown

4.81 out of 5 average rating, 155 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.

Casa particular in Chestertown

4.94 out of 5 average rating, 133 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!

Home in Chester

4.99 out of 5 average rating, 80 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.

Cottage in Saint Michaels

4.97 out of 5 average rating, 158 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

5 out of 5 average rating, 250 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.

Cabin in Queenstown

4.89 out of 5 average rating, 19 reviews

Cozy and Private 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.

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

Free parking on premises

Air conditioning

House rentals with a pool

Home in Saint Michaels

4.33 out of 5 average rating, 3 reviews

Celebrate the Season! Cozy Waterfront Escape

Home in Rock Hall

4.94 out of 5 average rating, 35 reviews

Rockfish Keeper

Home in Denton

4.95 out of 5 average rating, 20 reviews

*NEW* The Wilder Way

Home in Rock Hall

5 out of 5 average rating, 10 reviews

The Mariner's House

Home in Church Hill

4.89 out of 5 average rating, 53 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

Home in Stevensville

5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

Home in Millington

4.89 out of 5 average rating, 53 reviews

The Peaceful Getaway (with private pool & hot tub)

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