Holiday rentals in Stockton

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Private Home in Quiet Beach Country setting

Take a wander off the beaten path for cozy, quiet setting where ALL the stars come out at night. Quick access to area beaches, parks, ocean & rivers for water activities of all sorts and great country backroads that are cycling friendly! Unplug & relax from the hectic city life. The screened back porch offers an outdoor dining area with shaded mornings & fantastic evening sunsets. Enjoy a firepit with smores. RATE based on number of Guests. Over 2BRs/4 guests will increase rates modestly.

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

Countryside Home in Princess Anne

Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

Mary’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Mary’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. There is beauty all around on this property. You simply won’t want to leave! Just 20 minutes from Chrisfield There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Martha's Cottage” (check my profile for listing).

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

Island View House

On Chincoteague Bay’s iconic Public Landing waterfront - 180 degree view of Assateague Island's horizon from Ocean City to Chincoteague. Perfect for sunrises, sunsets, sky gazing, bird watching and watersports. Sleeps 6, two bedrooms two baths, private dock, raised decks, and sunroom. 30 feet from the water. Public Landing has great swimming, boating, fishing and crabbing. Public pier boat ramp, and beach are within short walking distance and there are no fees.

Tiny Gorgeous Waterfront Cottage

This cottage is 10 feet from the water. You'll wake up on a quiet slice of heaven. The road side faces the west for a beautiful sunset over the quiet corn field. The back side, faces the East. You look directly across at Assateague Island over the Bay. Our house is off the beaten path. This is great because it's an extremely quiet location, but also you are 11 minutes from anything. The closest store is 9 miles away. we love quiet coffees on the pier

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!