Holiday rentals in Clarksville, Howard County

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Top-rated holiday rentals in Clarksville, Howard County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Guest favourite

Flat in Annapolis

4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

Crow’s Nest Cottage - Down Under: 3BR/1BA garden-level duplex with fenced Zen garden, natural bamboo, water fountain, gas BBQ grill, brand new gourmet kitchen, sleeps 8. TV in all BR’s, steps to Chesapeake Bay waterfront. Sandy beach, protected swimming lagoon, park, bbq grills & picnic tables. Enjoy coastal Maryland’s beautiful flora & fauna. Nature lovers paradise, lower-level duplex (5 steps down) in waterfront community, access to pier, boat ramp, kayaks. Best vacation rental holiday home

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 155 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favourite

Cottage in Leesburg

4.92 out of 5 average rating, 406 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Top guest favourite

Cottage in North Beach

4.98 out of 5 average rating, 148 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Superhost

Home in Stevensville

4.89 out of 5 average rating, 47 reviews

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Guest favourite

Cottage in Pasadena

4.97 out of 5 average rating, 173 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Superhost

Cottage in Saint Michaels

4.84 out of 5 average rating, 31 reviews

Cottage #8 Herons Nest Lg 2 rooms Under Main House

OPEN March 25th to Nov 1st. every year. Herons Nest no 8 is located under main house, consist of full Kitchen, dining table, 1 queen size bed in separate bedroom, Living room Full size Futon open to a bed, 2 large sleeper recliners. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! room tax 4% due on arrival , 6% Abb collects please Bring waters . Boat info below. If need air mattress can bring.

Guest favourite

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Top guest favourite

Home in Sabillasville

4.93 out of 5 average rating, 115 reviews

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!

Guest favourite

Home in Arlington

4.84 out of 5 average rating, 112 reviews

Next to Virginia Hospital Center

Welcome to your future home away from home! This stunning 5-bedroom single-family corner house is the epitome of comfort and convenience. -A step a way from VHC hospital. - Metro bus stop at the end of the block - 5 car parking lot - has access to house without stairs, and walk in shower for those experiencing difficulty with movement or stepping over tub. -sleeps 10 guests comfortably (3 queen beds, 4 twin beds) -1.4 miles from Ballston metro stop

Guest favourite

Home in Annapolis

4.99 out of 5 average rating, 70 reviews

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!