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Vacation rentals in Hillandale

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Top-rated vacation rentals in Hillandale

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A three-story waterfront home is framed by lush trees and greenery. A spacious deck extends toward the sandy beach, furnished with several chairs and a swing. Kayaks are visible against the house, highlighting opportunities for outdoor activities along the Chesapeake Bay.

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.

A person is seen kayaking on calm waters, with a lighthouse in the background. The kayak is gray with orange and blue accents. The scene captures a peaceful moment on the water, emphasizing the tranquility of the Chesapeake Bay.

Apartment 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

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 154 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!

A charming stone cottage is set against a backdrop of lush trees and open sky. A gravel path leads to the entrance, with two chairs positioned on the grassy area, offering a serene view of the surrounding nature.

Cottage in Leesburg

4.92 out of 5 average rating, 403 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!

A serene outdoor fire pit area features four black Adirondack chairs arranged on gravel, inviting gatherings. In the background, a peaceful waterfront scene is visible, complemented by a view of boats and trees lining the shore.

5 out of 5 average rating, 4 reviews

The Waterside Nest

Escape to this serene 3-bedroom, 2-bath waterfront home in Middle River, blending modern coastal design with nature’s tranquility. Enjoy lounging on the deck with stunning beach and water views, fish from the shared pier, or kayak on calm waters. Inside, unwind in the open living area, cook in the chef’s kitchen, and relax in the luxury master suite. With a sandy beach, fire pit, hot tub, and easy access to dining, shopping, and attractions, this retreat is ideal for relaxation and adventure.

A screened-in porch features comfortable seating in shades of aqua and natural wicker. A round fire pit and a grill are positioned on the wooden deck, which is framed by greenery in the background. The solid door provides access to the cottage interior.

Cottage in Chesapeake Beach

4.93 out of 5 average rating, 87 reviews

Cozy Getaway - Breezy Point Beach

If you're planning a family trip, this 2 bedroom, 1 bathroom beach cottage will not dissapoint. Enjoy a cup of coffee or tea watching the sunrise from the screened-in porch. Listen to the waves while reading a book on the porch swing. Breezy Point Beach is located just steps away from a fun filled day of beach activities. For fishing and crabbing enthusiasts, there is a 200-foot pier for your pleasure. Jet Ski| Waterpark | Golfcourse mins away. Wheelchair Friendly| Free Parking| Free Wifi

Farm stay in La Plata

4.96 out of 5 average rating, 26 reviews

Oasis at Charity's Hope Farm Resort

Enjoy the perfect retreat for families, couples or anyone looking for rest and relaxation among a quiet, breath-taking location. This revived historic farmland is an icon in the area. Located just 30 miles outside of Washington DC, features a grand Victorian home w/ modern amenities. This small “farm resort” features pasture areas with alpacas, mini-cows, horses, chicks, bunnies, barns, a private pond for fishing, beautiful pool, large patio w/ outdoor fireplace, an indoor garden, and more.

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 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.

An aerial view of a colonial-style home with a brick exterior and multiple gabled roofs is presented. The property is surrounded by neatly trimmed hedges, and a spacious lawn leads towards a serene lakeside backdrop, visible through trees. A vehicle is parked in the driveway.

Guest suite in Warrenton

4.93 out of 5 average rating, 121 reviews

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

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!

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!

A clean, modern bathroom is presented with a glass shower enclosure and a white marble countertop. Black and white tiled flooring creates a classic look. Natural light enters through a window, enhancing the space's brightness.

Guesthouse in Arnold

4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

Immaculately designed separate guest suite/apartment in separate building with private entrance, private bath, Queen bed and gorgeous water views from every window. Guests have their own refrigerator, coffee maker and microwave and convection oven and air fryer, Xfinity tv 43" and high speed 5G internet for guests. Up to 2 guests can dine in the apartment or enjoy outdoor deck dining overlooking Lake Placid.

Vacation rentals for every style

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Popular amenities for Hillandale vacation rentals

Free parking on premises

Air conditioning

Stay near Hillandale's top sights

Papa John's Pizza24 locals recommend

The 4 Corners Pub15 locals recommend

McDonald's13 locals recommend

U.S. Food and Drug Administration10 locals recommend

Carlo Santucci Deli9 locals recommend

Jewel of India9 locals recommend

Other great vacation rentals in Hillandale

A modern kitchen space is highlighted by a white countertop and sleek cabinetry. Bar stools are positioned at the kitchen island, and appliances are integrated into the design. Soft lighting accentuates the area, creating a bright and clean environment.

Apartment in Georgetown

4.88 out of 5 average rating, 116 reviews

Cozy Modern Apt. In G-Town

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

A custom-built residence is presented with a blend of stone and wood accents. Large windows illuminate the inviting front porch, surrounded by manicured landscaping and a lush green lawn. The two-story structure is set against a backdrop of trees, offering a sense of privacy.

Home in Annandale

4.94 out of 5 average rating, 18 reviews

Family Ready Dogs OK Ping Pong Backyard EV Charger

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

A row of charming urban townhouses features a blend of red brick and stone exteriors. A large tree stands in front, providing natural shade. The street is lined with parked vehicles, indicating a vibrant neighborhood. The sky is bright with scattered clouds.

Apartment in Canton

4.97 out of 5 average rating, 31 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

Top guest favorite

The exterior of the house is showcased with a charming wrap-around porch, flanked by neatly trimmed landscaping. A three-story structure features shingle siding and multiple large windows that allow ample natural light. The front entrance is accessed via a set of stone steps.

Home in Arlington

4.97 out of 5 average rating, 100 reviews

Entire family size house steps to ANC & metro walk

Home in Tilghman Island

4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

Quick stats about vacation rentals in Hillandale

Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Hillandale?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with air conditioning, over 60 homes with a kitchen, over 60 homes with free parking, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Hillandale?
Experience the best of Hillandale with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Hillandale have free parking?
Absolutely! We offer over 60 house rentals with free parking in Hillandale. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Hillandale have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Hillandale. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Hillandale?
Yes! Work meets play with ease at over 70 vacation rentals in Hillandale featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Hillandale have wifi?
Absolutely! We offer over 60 house rentals with wifi in Hillandale. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Hillandale?
Hillandale has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Hillandale have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Hillandale. Enjoy a tailored experience with all the comforts you desire.

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