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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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, 288 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

A private in-ground pool is surrounded by a spacious patio, featuring lounge chairs with blue striped cushions. A small cottage is visible in the background, framed by trees and greenery, offering a peaceful outdoor retreat.

Guesthouse in Cambridge

5 out of 5 average rating, 27 reviews

The Place in Cambridge-Sailing into Autumn

The pool is open through September 30th Beautifully located, a clean crisp poolhouse cottage with key extras.! Queen bed, full kitchenette, and beautiful bath. Enjoy the lovely in-ground pool & poolside seating. Perfect for couples or small families. A block from the Choptank River, 1/2 mile walk downtown to shops and dining. Experience the Eastern Shore of the Chesapeake from a new perspective-it's your stay! The Place in Cambridge, sometimes, the best experiences come in simple packages.

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

4.92 out of 5 average rating, 26 reviews

Waterfront Home & 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, 129 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.

Superhost

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

4.94 out of 5 average rating, 104 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, 174 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

The exterior view showcases a spacious backyard with an inviting swimming pool surrounded by lounge chairs and blue umbrellas. A two-story gray house stands prominently, with a deck and seating area visible, all framed by greenery and a clear sky.

Home in Cambridge

4.97 out of 5 average rating, 123 reviews

Gorgeous, waterfront home - Perfect for Families.

If you were thinking of heading to the Eastern Shore, Casey's Porch is the place to go. Come and see for yourself. Bring your extended Family. Bring your friends. Enjoy the pool. Kayaks and paddle boards and bikes await you at this beautiful home on Hudson Creek. Fish from the dock. Pull crabs from the creek. Walk down quiet country lanes. Sit around the fire pit. So many fun, outdoor things to do. Casey's Porch has it all. First Floor bedroom, also.

Top guest favorite

Guesthouse in Stevensville

4.99 out of 5 average rating, 303 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 charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in Saint Michaels

4.98 out of 5 average rating, 108 reviews

SM’s Premier Rental Heated Pool (closes 10/28)

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.

Top guest favorite

A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.

Cottage in Easton

5 out of 5 average rating, 114 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

An aerial view of a spacious property featuring a private pool with a curvy shape. The home boasts multiple outdoor seating areas and is surrounded by a grassy yard. Solar panels are visible on the roof, and neighboring houses can be seen in the background.

Home in Tilghman

5 out of 5 average rating, 15 reviews

Waterfront Bliss: Ultimate Tilghman Retreat

ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This meticulously designed vacation home is tailored for the ultimate relaxation and adventure, offering a seamless blend of comfort, luxury, and outdoor excitement. Picture yourself returning from an exhilarating day on the Bay, gently mooring your boat to the private dock before plunging into the refreshing pool.

Guest favorite

Home in Saint Michaels

4.86 out of 5 average rating, 7 reviews

Crew's Quarters | an ESVR property

Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for social gatherings, especially for multiple couples looking to be within an easy walk into the historic town of St. Michael's . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Talbot County STR License STN-22-28