Vacation rentals in Westover

4.78 out of 5 average rating, 23 reviews

A spacious deck is equipped with several white Adirondack chairs, arranged for relaxing views. Large glass doors open from the home, complementing the light and airy atmosphere. The well-maintained lawn stretches out, providing a welcoming outdoor space.

Home in Ocean City

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Top guest favorite

The kitchen and dining area feature a spacious table set for six, surrounded by white chairs. A modern chandelier hangs above, while stainless steel appliances complement the white cabinets. A colorful backsplash adds visual interest, and natural light brightens the inviting open layout.

4.98 out of 5 average rating, 53 reviews

Central Location- Walk to Dining & Entertainment!

Experience the ultimate in coastal living at this beautifully renovated home, a stone's throw from the Beach road. Seasonal discounts available, this is your perfect getaway destination. The interior features a bright chef's kitchen with granite countertops and a tiled backsplash, an open-concept first floor with a cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath and balcony for serene morning views 🌄

A charming two-story cottage with a red metal roof features wraparound porches and white railings. The exterior showcases light-colored siding, while flower beds with greenery enhance the outdoor appeal. Clear blue skies create a bright backdrop for this inviting structure.

4.88 out of 5 average rating, 112 reviews

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

LOCATION, LOCATION, LOCATION!!! Located in the heart of Chincoteague, Sunny Claire is just steps away from downtown restaurants, shopping, theater, town park, fishing pier & carnival grounds. Relax in the hot tub, read a book or enjoy sunsets from one of the cozy porches, or just stroll along Historic South Main Street. This well appointed cottage offers the perfect vacation spot for your Chincoteague vacation. Sleeps 8 Master w/ King Sleep Number Bed Bedroom #2 (1 Q) Bedroom #3( 1 Q, 1 F)

Top guest favorite

Cottage in Frankford

4.99 out of 5 average rating, 150 reviews

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Top guest favorite

A sunlit living area features a cozy fireplace beneath expansive windows, allowing natural light to filter through. Comfortable seating is arranged around a central coffee table, with decorative elements that add a touch of warmth. A pleasing color palette complements the inviting decor.

Home in Selbyville

4.95 out of 5 average rating, 19 reviews

The Villa at Bayside Resort

Introducing a stunning, professionally decorated vacation rental property nestled in the heart of the prestigious Bayside Resort. Property Features: 4 beautifully-appointed bedrooms, 3.5 baths A spacious loft A sun-soaked living area Sun room, An elegant dining room, perfect for memorable family meals A scenic patio off of a wooded lot, offering a serene outdoor retreat. Bayside Amenities: Golf course 4 pools Fitness center Tennis courts Playground Kayaking Trails Concert Venue

4.9 out of 5 average rating, 112 reviews

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!

4.83 out of 5 average rating, 75 reviews

A sandy beach stretches along the riverfront, with a few colorful chairs and an umbrella positioned near the water's edge. Two cottages can be seen set back from the shoreline, surrounded by trees, providing a serene and spacious environment.

Cottage in Heathsville

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

A screened-in outdoor lounge area is furnished with a large sectional sofa and a wooden coffee table, creating a comfortable space for relaxation. A round dining table with metal chairs is positioned nearby, and natural light filters through bamboo shades, enhancing the cozy atmosphere.

4.98 out of 5 average rating, 45 reviews

cozy sunset cottage

Feel at home as soon as you walk in. Indulge in a coastal retreat that embraces you with a beach-inspired ambiance from the moment you arrive. Experience the carefree comfort of this centrally-located home, thoughtfully designed to exude a beach-like charm. And don't miss the special touch—an inviting screened-in outdoor lounge area where you can relax, unwind, and soak up the coastal vibes, creating cherished moments reminiscent of blissful days by the shore.

4.98 out of 5 average rating, 126 reviews

Home in Cambridge

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!

4.83 out of 5 average rating, 127 reviews

A wooden deck leads down to a gravel path surrounded by lush greenery. Two red chairs are positioned on the gravel area, enjoying the serene view of the woods. Soft landscape lighting is present along the path, enhancing the natural surroundings.

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.

5 out of 5 average rating, 18 reviews

A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and oven. A spacious countertop offers room for food preparation. Natural light enters through the window, illuminating the neutral-toned flooring and decorative elements on the wall.

Condo in Tangier

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!