Holiday rentals with a pool in Talbot County

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.

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)

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.

The Place in Cambridge-Summer is in the Air!

The pool is open! 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.

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.

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.

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.

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

Bayside Escape

Enjoy a relaxing stay at a family friendly home on the Eastern Bay. Bask in rosy hues as the sun sets over the Eastern Bay from the covered deck or the living room couch. Observe marine life in its natural habitat off of the dock. At our Bayside Escape you get two choices for how to cool off- float in the swimming pool or take a refreshing dip in the bay itself! This charming home has it all- space to work, play, and relax.