Holiday rentals in Stockton

4.81 out of 5 average rating, 146 reviews

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

4.89 out of 5 average rating, 284 reviews

Tiny home in Snow Hill

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.

4.99 out of 5 average rating, 90 reviews

Loft in Pocomoke City

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.

4.87 out of 5 average rating, 131 reviews

Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.88 out of 5 average rating, 65 reviews

Guest suite in Westover

The Hideaway Suite

Welcome to our humble farmhouse guest suite, your own little slice of tranquility nestled amongst the fields and forests. Tucked away from the hustle and bustle, our home is your perfect getaway, providing peace and quiet while still being conveniently close to Route 13. Once you step inside to the comfort of your suite on the second floor, you're in for a treat with beautiful views and idyllic sunsets. We look forward to hosting you in our lovely farmhouse.

4.75 out of 5 average rating, 211 reviews

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.86 out of 5 average rating, 189 reviews

Flat in Chincoteague

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

Guest suite in Chincoteague

4.98 out of 5 average rating, 288 reviews

Baywatch Upper-Waterfront & Roaming Ponies!

Discounted rates for weekly rentals Summer ‘25. Beautiful space in and out! Situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

4.85 out of 5 average rating, 136 reviews

Tiny home in Salisbury

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

4.98 out of 5 average rating, 107 reviews

Home in Pittsville

Wagon Wheel Cottage

Remodeled country farm house cottage that was built by our uncle in a quiet rural area surrounded by farm land. Other family members live all around us. It's located in the small town of Powellville, Md. It is 21 miles from Assateague, 20 miles from Ocean City, 12 miles from Berlin, 13 miles from Salisbury and 41 miles from Chincotegue VA. Sorry we do not allow pets as some guest have pet allergies.

Guest house in Pocomoke City

4.95 out of 5 average rating, 145 reviews

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

4.71 out of 5 average rating, 218 reviews

Flat in Snow Hill

Whimsical and Wonderful Retreat near the Ocean

This home is located in beautiful Snow Hill Md, which sets in between to popular beaches. You can be in Ocean City Md within 25 short miles ( all highway), or visit wonderful wildlife and ponies at Assateague Island MD, or Assateague Va, which is only 23 miles. Bridle parties for Castle Farms can stay and be at your event within 7 miles from my home.

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Other great holiday rentals in Stockton

4.93 out of 5 average rating, 14 reviews

Flat in Snow Hill

The Top of Downtown Snow Hill

HeatherRating, 5 stars3 weeks ago

Blair's condo was the perfect spot for our weekend trip. The condo was beautiful with all the necessities. It also has a good location, and is centrally located to Snow Hill shops and dining as well as a short drive from Assateague and Ocean City. We highly recommend this stay!

Home in Horntown

4.9 out of 5 average rating, 10 reviews

Campfire Bliss at the Beach

AngelaRating, 5 stars9 months ago

This is a lovely little spot in Trails End. Everything was modern and beautiful. The kitchen was so spectacular I cooked on vacation. Would go back many times and probably will.

5 out of 5 average rating, 10 reviews

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

JillianRating, 5 stars5 days ago

Had a wonderful stay! The entire family enjoyed the little beach and dock. Our son caught us crabs to eat every day and our daughter was in the water constantly! Very peaceful sitting on the back deck.

Home in Girdletree

4.61 out of 5 average rating, 56 reviews

Private Home in Quiet Beach Country setting

AmberRating, 5 stars3 weeks ago

We really enjoyed our stay! The home was cozy and it was very easy to get to the beach and nearby restaurants. The neighbors’ house was much closer than you could tell in the photos, so allowing our dog to use the backyard off leash wasn’t as easy as we had hoped. Otherwise, we had a great trip and loved the screened in porch!

4.88 out of 5 average rating, 113 reviews

Flat in Newark

Relax at the Shorehouse

MorganRating, 5 stars1 week ago

Margo was very nice and checked in with my throughout the weekend. The house was just as described and very clean! It was perfect for the two days we were there.

Houseboat in Snow Hill

4.64 out of 5 average rating, 39 reviews

Experience life on the water Houseboat!

JamieRating, 5 stars4 days ago

What a great long weekend for my husband and I! Think camper on the water and you’ll be set with your expectations. Our first time on a houseboat, but it certainly won’t be the last. So much included - bed linens, toiletries for the shower, soap, washcloths and towels for the bathroom and kitchen, nearly everything needed in the kitchen… even the coffee and filters for the coffee pot! We cooked our meals on the marina over the fire in the fire pit and on the black stone grill. Matt from the marina was there to greet us and answer any and all questions during our stay, and we had a cell to text in the event any issues arose. We spent the weekend outside crabbing, kayaking, and playing corn hole, and inside playing board games and watching movies. WiFi available so you could be as connected or not as you desire. Highly recommend both the hosts and the boat - you won’t be disappointed!

4.91 out of 5 average rating, 22 reviews

Home in Greenbackville

Knot Stressed in Captain’s Cove

DanielRating, 5 stars10 months ago

Thanks very much Virginia, we’ll see you again soon.