Holiday rentals with a pool in Somerset County

Year Round Playground - Rare Rustic-Modern Getaway

WINTER SALE 10%!! Feeling the fall & winter blues stuck in cramped city life? IMAGINE YOURSELF with a cup of hot cocoa surrounded by foliage, roasting s'mores by fire pit, enjoying hot tub under the stars feeling one with nature! Experience the magic of Eastern Shore in a one-of-a-kind waterfront retreat with a private dock on East Creek! This peaceful 3BR/2.5BA getaway offers the perfect mix of privacy and cold-weather comfort. Only missing piece is YOU! BOOK NOW & be the family vacation HERO!!

Condo-The Oasis on the Bay

Bayside Luxury Where Serenity Meets Style... Escape to this stunning upscale 2king &1queen, 2bath lakeside condo nestled on the water’s edge. This peaceful haven offers a rejuvenating getaway for adventure or relaxation. Cozy up by the fireplace in the stylish living room. Dine under sparkling chandeliers for glamour in the evenings. Enjoy breathtaking sunsets from the screened-in porch or patio lounge chairs. Take a dip in the pool, go fishing, or launch your boat from the private boat slip.

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!

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).

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!

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!

The Homestead at Sugar Water Manor Farm Stay

Located on 115 acres along the Manokin River, the Homestead offers full access to Sugar Water Manor's property, including kayaks, the pool, and opportunities to join the farm crew, collect eggs, or harvest produce. A breakfast treat is delivered daily. From the screened porch, enjoy the best sunset views over the river, gardens, and fields. Unplug during your stay--no WiFi, TV, or smoking on the property.

Big Cozy Loft Overlooking the Farm and River

Located above the apiary workshop, the Loft is a spacious kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens, Each morning, a farm-fresh breakfast is delivered. The Loft includes a small refrigerator plus coffee and tea essentials. Designed for a true retreat, there is no WiFi, TV, or smoking. Please note: children are not permitted.

Farm House Stay on the Eastern Shore of Maryland

Set on 115 acres along the Manokin River, Sugar Water Manor invites guests to enjoy kayaks, the pool, fire pit, and even join the farm crew to collect eggs or harvest produce. A breakfast treat is delivered each morning. The Farm House offers the property's finest views--river, gardens, barns, and fields all around. Unplug during your stay, as there is no WiFi, TV, or smoking on the property.

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!

Beautiful, Waterfront, Luxury

Welcome to "Hosta Cottage!" - a fabulous vacation home located in Temperanceville! Enjoy all the fine features this charming villa 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!

Creek House - Luxury Waterfront on Holden's Creek

Welcome to "Creek House!" - a fabulous vacation home located in Temperancville! Enjoy all the fine features this charming abode 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!