Vacation rentals with outdoor seating in Assateague Island

Salty Roots Retreat_Huge Yard_FirePit/Kids&Groups

Experience the perfect beach getaway in Rehoboth Beach.This stunning 5-bedroom, 2-bath home offers an open-concept kitchen and living area, ideal for family gatherings. Relax in the expansive private backyard featuring a deck and fire pit area—perfect for games and evenings under the stars. Just moments from beaches, restaurants, shopping, waterparks, and vibrant nightlife. Fully equipped kitchen, coffee bar, & all linens provided for your comfort and convenience. Book your dream vacation today!

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

*Location* Beach retreat walk to Rehoboth Ave

Location!! Location! Location! Walk to all the restaurants and bars Rehoboth has to offer. Newly renovated in 2020 our townhome is .4 miles, 10 min walk to Rehoboth Ave. We are beachside of Route 1. We have dedicated parking in front of our house for guests. Enjoy our outdoor deck patio with OUTDOOR shower, grill, fire table and sectional for a chill hangout in private yard after a fun day at the beach. TV’s have cable and streaming services so you can sit back and relax at the end of the day

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

Outside space - Urban Camping bring a tent or RV

Quiet backyard with beautiful holly and magnolia trees plus ornamental grasses, butterfly bushes, native plants, vegetable plants and a variety of blooming flowers. Bring your tent and camping supplies, sleeping bag, air mattress, etc. There is a large parking area for a camper or vehicle with pull camper. This is an outside area for camping. There is a picnic table, lounge chairs plus table and chairs for your use. Walking distance to the zoo, park, shopping center and restaurants.

Patrick's Creekside: 4 Peeps-Ur Doggies! 420-Bark!

Patrick's Creekside is free to your pooches - barking allowed, 420 friendly on your private deck, half a mile to the bike trail. Private entry to this 2nd story (2rm,2beds/queen bed & full sofa bed) 1 BR apartment with one full bathroom for a max of 4 humans and a handful of dogs. A good fit if you don’t mind who gets the sofa bed with bathroom access thru the master. Mini kitchen:Keurig, fridge, coffee, crockpot, backyard with little trail! Check out Timmy’s Treeside also.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

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.