Vacation rentals with a pool in Talbot County

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Top-rated rentals with a pool in Talbot County

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

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Guest favorite

Cottage in Royal Oak

5 out of 5 average rating, 11 reviews

Newly Renovated Summer Paradise-Pool-Tennis-Garden

Our newly renovated garden cottage is nestled on an 18 acre waterfront private retreat with access to a swimming pool, gym, tennis court & private dock! The kitchen is fully-equipped with stainless steel appliances and laundry located in house. The cottage shares the grounds with a few other of our private cottages. Guests also have access to kayaks, fishing equipment, the fire pit, ice cream shop, library and more! Quiet and remote but very close to both Easton and Saint Michaels for a perfect

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, 274 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 inviting outdoor area features shaded seating around a clear inground pool. Comfortable lounge chairs are positioned on a brick patio, surrounded by trees and landscaped plants. Tables with decorative elements add charm to the space, providing a relaxing environment.

Home in Stevensville

4.98 out of 5 average rating, 51 reviews

The Pool House in Romancoke On The Bay

Spacious 4 bedroom home on Kent Island minutes from multiple wedding venues. Inground pool with sunny & shaded sitting areas for everyone to enjoy. Pergola brick patio w/table & a deck with a bar for outdoor meals and a fully fenced back yard for your dog. Additional fee per dog. Living room with Fireplace, Sunny family room, nicely equipped Kitchen, all just a block from the Eastern Bay if you have beach strolling, kayaking or paddle boarding in mind. South Island Bike Trail just a block away.

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, 156 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.

Guest favorite

An aerial view showcases a spacious backyard featuring a private in-ground pool surrounded by lounge chairs. The large lawn is framed by trees, with the remodeled two-story home visible in the background, characterized by large windows and outdoor seating areas.

Home in Easton

4.94 out of 5 average rating, 17 reviews

Waterfront Home w/ POOL near St. Michaels & Easton

Beautiful WATERFRONT 4 bedroom/4 bath home with a large 3.5 acre yard and private in-ground POOL, dock, fire pit & kayaks! Our family recently purchased and remodeled the entire home. Everything is new! The home is located minutes between Easton and St Michaels. Each bedroom is very spacious and 3 of the bedrooms have King beds. The "kids" room has a Queen over Queen bunk bed and another queen bed. There is a separate TV and rec room for kids too! STRN 23-54 (Talbot County license number)

Top guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 119 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Guest favorite

Home in East New Market

4.94 out of 5 average rating, 32 reviews

Waterfront Private Dock & Pool Near Cambridge

Escape to tranquility on our serene 1-acre property, perfect for birdwatching enthusiasts. Enjoy exclusive access to a private dock, two kayaks, fishing and a refreshing in-ground saltwater pool. Unwind in our spacious 5-bedroom, 2.5-bathroom home, equipped with TVs, streaming services, and high-speed internet throughout, allowing you to stay connected while you relax. Conveniently located 10 min from the Hyatt & 15 min from Historic/ downtown Cambridge. Your peaceful retreat awaits!

Guest favorite

A spacious backyard showcases a private pool surrounded by lounge chairs. The house, featuring a classic design, is set against a backdrop of lush greenery and trees, with a screened porch visible to the left, creating an inviting outdoor retreat.

Home in Easton

5 out of 5 average rating, 49 reviews

Tuckaway Cove Relaxing waterfront property

Tucked away on a beautiful, quiet cove off the Miles River, with a large yard for playing, a private pool & dock, & kayaks for water fun, Tuckaway Cove provides all the perfect ingredients for a relaxing, memorable family vacation! The home is fresh & bright, comfortable & spacious with a nautical theme throughout. The location is private, but conveniently located between Easton and St Michaels, close to everything you need! Licensed by Talbot County, MD #ST-851-MIL 2019

Top guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 160 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

A spacious outdoor area features a rectangular pool surrounded by a paved deck. Lounge chairs and tables are arranged around the pool, with a covered seating area visible in the background. A hot tub is positioned nearby, enhancing outdoor leisure options.

Home in Stevensville

5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

Bring the whole family (including the furry ones) to this great home with lots of room for indoor and outdoor fun and relaxation. Located near the Chesapeake Bay and walking distance to local beaches, an 18 hole executive golf course, equestrian park, paved walking/bike trail. Close to restaurants, fishing pier, boat ramps, and shopping. A short drive to Annapolis and the United States Naval Academy. Less than and hour's drive to Washington DC or Baltimore.

Top guest favorite

Guesthouse in Stevensville

4.99 out of 5 average rating, 270 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.

Top guest favorite

A private pool area is surrounded by lush green grass, featuring a rectangular swimming pool with clear blue water. Lounge chairs are arranged around the pool, and a shaded seating area is visible nearby, providing a relaxed outdoor environment.

Home in Saint Michaels

4.98 out of 5 average rating, 100 reviews

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.