Holiday rentals with a pool in Somerset County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Somerset County

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

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Superhost

Farm stay in Westover

The Farm

Three places in one located on Sugar Water Manor with full access to the property- fire pit, pool & more. The Farm is a combination of the Farm House-3 bedrooms, 1.5 baths & a dining room, living room and porch that will all seat everyone. It also has an eat-in kitchen. The Homestead is just a short walk down the farm lane -2 bedrooms, 1 bath, living room, dining room, porch & full kitchen. Next to the Homestead is the Loft- a private suite for up to 2 adults with a large bath, table and desk.

Top Guest favourite

Farm stay in Westover

5 out of 5 average rating, 68 reviews

Farm House Stay on the Eastern Shore of Maryland

Sugar Water Manor sits on nearly 115 acres of farm and woods on the Manokin River. Guests have full access to the property including kayaks, fire pit, pool and can make arrangements to enjoy the farm crew, collect eggs and harvest for your meals. A breakfast treat will be delivered each morning . The Farm House has the best views of the property. With views of the river, garden, both barns and farm you will not know where to look first. Unplug- no WiFi/TV or smoking on property.

Top Guest favourite

Farm stay in Westover

5 out of 5 average rating, 86 reviews

Big Cozy Loft Overlooking the Farm and River

The Loft is located above the apiary workshop. It is an expansive king room with bath. Walk-in shower has a rainforest head. Views of the donkey pasture out your window! From one side you have a view of the farm & river, the other apiary, gardens & river. The loft is the perfect place to cozy up. Each morning you will have a farm fresh breakfast. The loft has a small refrigerator, tea, coffee with all your necessities. No WiFi/TV or smoking on property. No children in Loft.

Top Guest favourite

Farm stay in Westover

5 out of 5 average rating, 58 reviews

The Homestead at Sugar Water Manor Farm Stay

The Homestead at Sugar Water Manor sits on nearly 70 acres of farm and woods on the Manokin River. Guests have full access to the property including kayaks, the pool and can make arrangements to enjoy the farm crew, collect eggs & harvest for your meals. A breakfast treat will be delivered for your breakfast. It has the best sunset views from it’s screened in porch. With views of the river, garden and farm you will not know where to look first. No WiFi/TV or smoking on property

Home in Deal Island Historic District

1 Mi to Boat Ramp: Peaceful Deal Island Home!

Large Backyard w/ Pool | Near Fishing & Bird-Watching Yearning for an idyllic getaway with your loved ones? Look no further than this vacation rental in Deal Island Historic District! This 2-bedroom, 1-bath home boasts a screened porch and convenient proximity to the bay, making it easy to enjoy nature at its finest. Spend your days swimming, boating, or soaking up the sun. At night, gather around the fire pit and gaze at the stars. Your next East Coast escape begins here!

Guest favourite

Farm stay in Princess Anne

4.94 out of 5 average rating, 99 reviews

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Superhost

Cottage in Marion Station

4.72 out of 5 average rating, 39 reviews

Year Round Playground - Rare Rustic-Modern Getaway

Enjoy best of Eastern Shore living in this unique property that provides privacy & exciting amenities for everyone: POOL, 7 PERSON HOT TUB, OUTDOOR KITCHEN, REC ROOM, FISHING, w/GOLFING & BEACHES nearby! Newly renovated 3BR/2.5BA offers guests an opportunity to have in-the-woods feelings w/o sacrificing comfort. Escape the city rushes on a rare waterfront property w/private dock on East Creek leading out to the bay! Don’t miss out on Insta-worthy photo ops! BOOK NOW!!!

Condo in Crisfield

Walk to Main St: Condo w/ Pool Access in Crisfield

Community Pool | Marina On-Site | Walk to Ferry Terminal Rest and relaxation await at this 3-bedroom, 2-bath vacation rental condo in Crisfield, Maryland. Enjoy the serenity of the morning with scenic water views of Daugherty Creek while sipping coffee on the private screened balcony. Then, peruse the local shops, hop on the ferry to explore Smith Island, or spend an afternoon lounging at Crisfield’s Wellington Beach. Your next getaway is just a click away!

Top Guest favourite

Apartment in Crisfield

5 out of 5 average rating, 8 reviews

Newly renovated 3 Bedroom Condo

Relax and enjoy time away with stunning sunsets and water views! Discover the Eastern Shore first hand and fish or crab off the dock. Condo is on the top floor with a balcony and screened in porch for additional entertaining. Access to the community pool and kayak or bicycle around town. Walking distance to quant shops and great restaurants. Everything you need right outside your front door and don't miss out on daily ferry to Smith Island!

Apartment in Crisfield

5 out of 5 average rating, 3 reviews

Waterfront Condo Getaway

This stylish place to stay is perfect for family getaways, girl trips and everything else. Located in the waterfront community of Crisfield, Md., with access to Smith and Tangier Islands, local seafood restaurants, kayaking trails and Janes Island State Park all located nearby. Ocean City, Md and Assateague beaches are about 1 hr. away. There is a great pool, wraparound deck and screened porch for enjoying those evening sunsets!

Home in Temperanceville

The Porter's Barn - waterfront w/ dock & fire pit

Welcome to "Porter's Barn at The Creek!" - a fabulous vacation flat located on Chincoteague Island! Enjoy all the fine features this charming cottage has to offer, and remember, you're renting the *entire* place which means you don't have to share! After all, this is... #WhereGreatVacationsHappen ...on Virginia's Eastern Shore!