Vacation rentals with a pool in Somerset County

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.

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.

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

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).

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!!!

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 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!