Vacation rentals with outdoor seating in Assateague Island

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Top-rated outdoor seating rentals in Assateague Island

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Guest favorite

Condo in Berlin

4.98 out of 5 average rating, 103 reviews

Amazing Waterfront in Berlin, MD- Sea Breeze Suite

1 of 5 waterfront units (Drift Inn, Sea Breeze, Coconut Grove, Coral Tides, Day Break) located at The Inn on Turville Creek in West Ocean City. Perfect for outdoor lovers or a quiet escape. Bring your paddleboards, kayaks, or just enjoy the beautiful views from the comfort of your own patio. The Inn is located approximately 5 miles from downtown Ocean City and the town of Berlin, MD (voted America's Coolest Small Town) and ~10 miles from Assateague. Stunning sunsets right from your front patio!

Sep 16 – 23

R3,571 ZAR per night

Guest favorite

Tiny home in Accomac

4.93 out of 5 average rating, 442 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

Oct 1 – 8

R2,322 ZAR per night

Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 109 reviews

Waterview Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Dec 25 – Jan 1

R2,612 ZAR per night

Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 177 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Jan 9 – 16

R3,356 ZAR per night

Guest favorite

Home in Chincoteague Island

4.97 out of 5 average rating, 179 reviews

★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★

Fully equipped 1000 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes & Private Dock. Linens & towels included Jay's Retreat is at nature's front door within a few miles from Assateague National Seashore (the beach), home of the world famous Chincoteague Ponies. Enjoy: Swimming in the bay and ocean Bicycling Fishing, crabbing, clamming Kayaking, paddle boarding; boating Hiking Bird Watching Nature photography Hunting Nature Trails Great Restaurants & Brew Pub Boat Tours Ponies

Dec 31 – Jan 7

R2,518 ZAR per night

Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 227 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Nov 8 – 15

R2,088 ZAR per night

Guest favorite

Cottage in Onancock

4.97 out of 5 average rating, 198 reviews

Escape to the Eastern Shore - Upscale Waterfront

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles

Nov 24 – Dec 1

R3,404 ZAR per night

Guest favorite

Guest suite in Chincoteague

4.93 out of 5 average rating, 229 reviews

Baywatch North-Waterfront & Roaming Ponies

This is a lovely space! 2 queen bedroom unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, patio cooking area shared with upstairs unit, bbq grill, fantastic view, beach items, plenty of parking, private lane, very quiet out of the way of everything, super laid back host living in the other portion of the house. Labrador and cat on premises, ponies on premises!

Nov 3 – 10

R1,667 ZAR per night

Guest favorite

Condo in Ocean City

4.9 out of 5 average rating, 145 reviews

Oceanside Oasis - Stylish Condo Steps to the Beach

Beautifully renovated one-bedroom condo just steps to the beach. Centrally located on 35th street our unit is close to shopping, restaurants, the Convention Center, and the boardwalk. Our private patio has a view of the beach and ocean, and the spacious kitchen has more than enough room to have some friends over for a meal. Located in Midtown, this area is full of nightlife, amazing restaurants, and a less crowded beach since there aren't any large hotels.

Nov 9 – 16

R2,071 ZAR per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 157 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Oct 20 – 27

R2,018 ZAR per night

Guest favorite

Guest suite in Ocean City

4.98 out of 5 average rating, 273 reviews

Spacious Luxury Studio in Ocean City

The Elbridge is a luxury studio apartment in downtown Ocean City. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants and the boardwalk, The Elbridge is truly special.

Oct 12 – 19

R3,545 ZAR per night

Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 176 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

Dec 19 – 26

R2,289 ZAR per night