Holiday rentals with a hot tub in Talbot County

A large window fills the space with natural light, offering views of the tranquil waterfront and grassy area. A small desk and chair are positioned nearby, while outdoor seating is visible on a stone patio outside.

4.97 out of 5 average rating, 73 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.

Guest suite in Queenstown

River Guest Suite w/ Pool, Beach, Private BoatSlip

Enjoy some rest & relaxations on the river with an unbeatable sunset! This guest suite offers 2 private bedrooms & a private bathroom suitable for two couples or a family! It also includes a large private living room with a 85 inch flatscreen TV & a private bar! In addition a newly added full indoor private kitchen. As well as a pull out couch that becomes a bed, size full. Your stay comes with a personal escort from our farm dog, Reef! He’s an old yellow Labrador who loves making new friends!

4.98 out of 5 average rating, 45 reviews

4.88 out of 5 average rating, 200 reviews

A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.

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!

5.0 out of 5 average rating, 31 reviews

Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock

Cattail Cove: Your perfect riverside escape! Nestled on 4 scenic acres along the river, our property offers a peaceful respite for family&friends. Sip your coffee overlooking the river as bald eagles dive for their breakfast, and then relax in the heated saltwater pool before crabbing from our brand-new private pier! Included Amenities: -Saltwater Pool: seasonal -Hot tub open all year! -Stone Fire Pit -Kayak, paddle board, canoe -Private boat launch area Max Guest Count is 13 total people

Superhost

An open living and dining area features a high ceiling and abundant natural light. A cozy fireplace is positioned between two seating areas, each adorned with comfortable sofas. A dining table with modern chairs occupies one corner, while large windows overlook the outdoor space.

Home in St. Michaels

Crew's Quarters | an ESVR property

1/2 Mile to Historic District, Pickleball Court, 3 Private Suites! Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for friends and family, especially for multiple couples looking to be a short drive 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. Extra large windows through-out provide wonderful views

4.89 out of 5 average rating, 9 reviews

The historic waterfront home showcases a large saltwater pool surrounded by lounge chairs. The expansive backyard features a well-maintained lawn, with the house's charming architecture and three porches visible in the background under a clear blue sky.

5.0 out of 5 average rating, 73 reviews

River Lure estate - Waterfront, Pool, Hot Tub

River Lure is a beautifully restored historic waterfront home on the banks of the Choptank River, 3 blocks from downtown Cambridge, MD. The 5 bedroom, 3 full/2 half bath waterfront home features a new salt water pool & hot tub overlooking the river, plus a huge yard & private dock. Perfect for families, the entire 3rd floor is a kid's bunk room paradise. Stroll into town to bars & restaurants, River Lure is steps from the Cambridge Marina and Lighthouse; walk to Ironman & Eagleman start.

A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.

4.94 out of 5 average rating, 187 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.

Superhost

A spacious outdoor area showcases a well-maintained lawn surrounded by trees. A large deck is furnished with seating, while a private hot tub and BBQ grill add to the outdoor amenities. The house features multiple sections, enhancing the inviting atmosphere.

Home in Chester

Waterfront Hot Tub, Fire Pit & Views

Sink into the hot tub and watch the sun set over the Chesapeake Bay. This waterfront home in Chester has everything you need to unplug — a 270-degree sunroom with stunning water views, a fire pit for evening hangouts, a cozy indoor fireplace, and two comfortable bedrooms that sleep up to 8. The full kitchen is ready for group meals, and the sofa bed adds extra space. Minutes from Kent Island restaurants and the Bay Bridge. Annapolis and the Eastern Shore's best spots are an easy drive.

4.89 out of 5 average rating, 27 reviews

4.95 out of 5 average rating, 65 reviews

A serene waterfront view captures a sunset over Crab Alley Bay, reflecting warm colors on the water. A private pier extends into the bay, with a boat anchored nearby. Lush green grass leads to the water's edge, framed by trees in the background.

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!

5.0 out of 5 average rating, 126 reviews

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

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

4.87 out of 5 average rating, 23 reviews

An inviting pool area is showcased, featuring a clear blue water pool surrounded by several sun loungers and umbrellas. A hot tub is situated at the edge of the pool, framed by lush greenery and open space, enhancing the serene outdoor setting.

Home in St. Michaels

St. Michaels Waterfront Retreat | Pet Friendly

Escape to the quieter side of St. Michaels at this spacious retreat. Spend crisp mornings overlooking the water, afternoons wandering the shops and restaurants of St. Michaels, and evenings gathered back at the house. With beautiful interiors, generous gathering spaces and plenty of room for your four-legged companion, it’s made for family weekends, trips with friends and slower days on the Eastern Shore. Talbot County Licensure: STRN-25-30

Superhost

A scenic waterfront view is captured, featuring a spacious green yard with a double swing and a hammock situated under a tall tree. Calm waters reflect the sky, creating a serene atmosphere. Lush greenery lines the shore, enhancing the peaceful setting.