Holiday rentals with a hot tub in Talbot County

4.97 out of 5 average rating, 60 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

Quiet waterfront cozy home w/ pvt pier, hot tub, kayaks, grill, massagechair & fire pit. Experience life on the river in a 2bedrm/1 bath-shower/3bed Retreat on a cove off the ChoptankRiver. About 15-20mins toHistoricCambridge/Restaurants/groceries. Easy day trips to St.Michaels/Tighlman/Oxford/Tubman; 75-90min drive to Ocean City/Rehoboth beach. Waterviews from beds. Relax in screened porch w/ waterviews. Watch sunrise/sunset in pvtpier/kayak/hottub. Bring fishing rods/crablines/baits-seasonal.

5 out of 5 average rating, 8 reviews

Home in Chester

Waterfront House: Hot Tub, Fire Pit, & Views

Escape to a stunning Waterfront Getaway on Maryland's Eastern Shore! This charming house offers breathtaking water views, a private hot tub, and a cozy indoor fireplace, perfect for a relaxing retreat. With two bedrooms, it comfortably accommodates families or groups, providing amenities like a BBQ grill, a fully equipped kitchen, and a beautiful patio to enjoy the outdoors. Located in Chester, you'll be close to local attractions and enjoy the tranquility of waterfront living. Experience the be

4.87 out of 5 average rating, 182 reviews

Home in Annapolis

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay 100ft away. Water views from most rooms plus treehouse vibes. 4 bedrooms + 4 full bath. Custom luxury upgrades, new appliances. Pull out daybed +2 folding queen mattresses, rustic leather sectional sofas can sleep 4 more (14+total), outdoor grills, covered balconies, hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

4.95 out of 5 average rating, 98 reviews

Home in Stevensville

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

4.84 out of 5 average rating, 19 reviews

Hambrooks Home with Hottub/Mid Term stays welcomed

Welcome to my 2 bedroom/2 bath, an office(with 2 smaller 72x38 inch floor mattresses) so you can keep your nose to the grindstone if desired, and also a Hot tub! The Home is situated a stones throw outside of the city limits, but close enough to Downtown, The Choptank River, and all the area has to offer. Watch the sun rise on the front porch with a cup of coffee, or enjoy the back deck and Hot tub while the sun sets. Reading material, games, and fun stuff for the kiddo's also obtainable.

4.93 out of 5 average rating, 149 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

4.74 out of 5 average rating, 85 reviews

Home in Saint Michaels

Two Oysters House 2025 Remodel

The Two Oysters House finished renovations in 2025. The house is on the water with private (salt water) pool and dock situated in a peaceful country retreat in St. Michaels, Md just 2.5 mi. from the center of town (Inn at Perry Cabin and Museum). Bikes and kayaks are included in the rental rate. 4 bedrooms plus den 3 full baths. 2 Mastersuite with private bath. We prefer weekly rentals in the summer. 3nt.min stay. Pool/spa open in the summer, please check with us for exact dates.

4.96 out of 5 average rating, 51 reviews

Home in Chester

A waterfront Paradise with hot tub

Retreat with family, friends or team member to an idyllic waterfront house that faces west. That means, you will see the most beautiful sunsets of the Chesapeake Bay from the living area, the deck or the pier while relaxing. Open concept kitchen connected to the social area of a fully renovated home. Very well, equipped kitchen with fancy details. The huge backyard offer plenty of room for having fun outside doing, a fire pit or playing outdoor games. Two TV rooms. This is a paradise!

4.75 out of 5 average rating, 4 reviews

Home in Royal Oak

September Splender! Waterfront ,Pool, Dock, Hot Tu

Deep water dock will accommodate a 52' yacht! Catch fresh fish and go crabbing, and two kayaks are available. The views are wide open and can be enjoyed from most (Website hidden by Airbnb) sparkling pool is adjacent to a large porch where you can watch the kids, have a crab feast, or just enjoy the expansive water views. Celebrate the end of a perfect day by viewing the sunsets.You may arrive by water, MLW depth is 4 1/2-6 feet/end of the dock. Will accommodate 40 ' sailboats.

4.9 out of 5 average rating, 10 reviews

Home in Grasonville

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family! **Located in the Prospect Bay Country Club just 15 minutes east of the Bay Bridge. Relax every evening in the back yard. The setting is incredibly peaceful and a wonderful romantic escape for a family getaway. Find peace and reconnect with nature at this amazing short term rental with 45 feet of undeveloped creek view. **This spacious home can sleep a MAX of 6 guests. 3br and 3.5 baths!**

5 out of 5 average rating, 11 reviews

Historic and Spacious Stewart House

This 18th Century Victorian home has been lovingly restored and furnished. It boasts 8 beautifully appointed bedrooms (2 king, 5 queen and 1 double twin rooms) and 5 1/2 baths, formal dining room, eat-in kitchen, den, laundry room, two working fireplaces, upper deck, large, landscaped backyard with a jacuzzi spa, firepit, large outdoor seating area with barbeque and more. Convenient location on High Street just blocks from downtown restaurants, bars and boutiques.