Top Maryland Vacation Rentals

1

Chesapeake Hospitality

Greenbelt, Maryland

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+1 (301) 474 - 3307

The most unique entry on this list, Chesapeake Hospitality doesn't offer any properties to rent. What it DOES offer is an exceptional third-party hotel management. So if you were flipping through this list and... read more

The most unique entry on this list, Chesapeake Hospitality doesn't offer any properties to rent. What it DOES offer is an exceptional third-party hotel management. So if you were flipping through this list and thinking to yourself, "Man, I wish MY company was good enough to be put on a list like this!", these are the people that can help you do so.

With an immaculate track record of successful operations and outstanding financial performance, Chesapeake Hospitality also has an unparalleled reputation for results, and has for almost 60 years. Whether you are a private equity, institutional, or individual hotel investors/owners, Chesapeake Hospitality presents a unique opportunity to experience what’s possible with a results-driven hotel management partner. What can you expect? Quality, first and foremost. Honesty, integrity and humility are the values the company was founded on, and they're experts at balancing ownership’s strategic vision with the practical immediacy of day-to-day operational demands.

Address

6404 Ivy Ln #800, Greenbelt, MD 20770

Population

Greenbelt's population was 23,068 at the 2010 U.S. Census.

Fun facts

reenbelt was one of three "green" towns planned in 1935 under the United States Resettlement Administration

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2

Tidewater Vacations

St. Michaels, Maryland

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+1 (410) 745 - 5255

St. Michaels has been consistently voted (in various publications) as one of the best places to vacation in the state. Tidewater Vacations invites you to come and experience why!Self-described as the "Hamptons of... read more

St. Michaels has been consistently voted (in various publications) as one of the best places to vacation in the state. Tidewater Vacations invites you to come and experience why!

Self-described as the "Hamptons of the Chesapeake Bay", Tidewater Vacations offers a bevy of properties, amenities, and hospitality, the likes of which most guests have never seen before. Their huge inventory of holiday rental homes are full of serenity, style and comfort, all wrapped up in a waterfront setting. All properties have private pools, docks, and many have tennis courts. Feel like living luxuriously? Each property offers full concierge service, so hire your own personal chef and have an authentic Eastern Shore Crab Feast!

Address

300 N Talbot St, St Michaels, MD 21663

Highlights

The concierge team can help you arrange your own private chef, a rental boat, massage therapists, and even suggest where to grab an exquisite dinner.

Fun facts

Southern Living Magazine ranks St. Michaels in the top 3 "Best Small Town Getaways"!

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3

7C's Lodging

Flintstone, Maryland

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+1 (301) 478 - 3535

7C's Lodging's sole goal is to bring a touch of country and relaxation into a fast paced world. When you commit to staying in a 7 C's property, you commit to a relaxing and restful vacation. What else would you... read more

7C's Lodging's sole goal is to bring a touch of country and relaxation into a fast paced world. When you commit to staying in a 7 C's property, you commit to a relaxing and restful vacation. What else would you expect from a place named after cozy, convenient, comfortable, clean, classic, country, cabins?

First things first" 7 C's advises you to not let the word "cabin" fool you! You won't be sitting in a poorly-ventilated shack off in the middle of nowhere. Instead, you'll be staying in a veritable hotel room nestled in a cabin, featuring all the comforts of home and plenty more. The list of amenities stretches from here to Baltimore, but here are a few: walls of knotty pine (some also have stone), contemporary air conditioning and heating, an eating area with a microwave, refrigerator, coffee maker and condiments, dish network television, cathedral ceiling and a complete bath with shower and modern amenities. Each cabin also has a front porch where you can just sit, relax and enjoy the mountain scenery. What better way to enjoy the beautiful Maryland countryside?

Address

21530 National Pike NE, Flintstone, MD 21530

Highlights

Cabins offer two double beds, two queen beds or one king bed along with knotty pine walls and a cathedral ceiling with a ceiling fan

Getting there

The entrance just 50 yards from Eastbound Exit 56 off Interstate 68.

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4

Yellowstone Villages

Oakland, Maryland

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+1 (800) 336 - 7303

One of the newest additions to the Oakland area, Yellowstone Villages are a collection of luxurious villas, flanked by majestic vistas and supported by a dedicated (and incredibly hospitable) staff.Yellowstone... read more

One of the newest additions to the Oakland area, Yellowstone Villages are a collection of luxurious villas, flanked by majestic vistas and supported by a dedicated (and incredibly hospitable) staff.

Yellowstone Villages excels in catering to large groups. Family reunions, business retreats, and team-bonding weekends will be incredibly comfortable and satisfied with the proximity to Oakland's cornucopia of things to do. Each beautifully wooded property offers the private get-away feel most seek, but they're still close enough to each other that the kids can go out and play when they feel like it. Adults will be able to relax in comfortable furnishings, and will rest easy knowing that they're surrounded by a great village community, populated with your coworkers, family, or friends.

Address

35 Towne Centre Way, McHenry, MD 21541

Highlights

The Autumn Glory Festival, a fall festival that attracts a great number of tourists, takes place in Oakland every October.

Related activities

Within walking distance, guests will find the local movie theatre, Arrowhead Market & Convenience Store, Uno’s Pizzeria as well as several shopping stores.

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5

Central Reservations

Ocean City, Maryland

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+1 (877) 736 - 8621

Central Reservations doesn't promise its guests anything that it can't deliver on. So you know that when they claim to offer the best resort vacation rental properties in Ocean City, they have the homes, locations,... read more

Central Reservations doesn't promise its guests anything that it can't deliver on. So you know that when they claim to offer the best resort vacation rental properties in Ocean City, they have the homes, locations, and hospitality to back it up.

There's simply no better way to experience beautiful Ocean City than with Central Reservations. All of their condos, townhouses, and homes are supremely located so as to offer easy access to the ten miles of white beaches the city is famous for. Take a stroll on the boardwalk, get out on the water for some sports fishing, or have a blast at a nearby waterpark; your mind will be at ease knowing you have an incredibly luxurious, spacious, and well-stocked rental just waiting to be enjoyed. You owe it to yourself to make a reservation at Central Reservations!

Address

6200 Coastal Hwy #100, Ocean City, MD 21842

Population

7,092 as of 2013

Related activities

Make sure you check out the adjacent Jolly Roger Park, comprised of SpeedWorld, Splash Mountain, Jolly Roger at 30th Street, and Jolly Roger at the Pier. Fun for the whole family!

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6

Century 21 New Horizon

Ocean City, Maryland

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+1 (800) 756 - 8223

Century 21 New Horizon is a company that is known throughout the US for its quality, personal service, and fantastic locations. Century 21 New Horizon in Ocean City is no exception to that mold.The incredibly... read more

Century 21 New Horizon is a company that is known throughout the US for its quality, personal service, and fantastic locations. Century 21 New Horizon in Ocean City is no exception to that mold.

The incredibly friendly staff at Century 21 New Horizon will help you search for the perfect Ocean City rental, one that will personalize and enhance your vacation experience. Since 1982, Century 21 New Horizon has proven again and again that they know how to handle guests, both first-timers and returners. Opulent accommodations and pristine vistas are a certainty, as is the fun you'll have at Ocean City's plethora of amusement parks, restaurants, and various other attractions!

Address

8606 Coastal Hwy, Ocean City, MD 21842

Highlights

Ocean City now extends just more than 9 mi (14 km) from the southern inlet to the Delaware line.

Fun facts

During the summer, Ocean City becomes the second most populated town in Maryland.

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7

Taylor-Made Deep Creek Vacations & Sales

McHenry, Maryland

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+1 (866) 351 - 1119

With a wide array of homes and an innovative sense of style, Taylor-Made Deep Creek Vacations & Sales invites you to stay in a opulent rental and experience the majestic beauty of Deep Creek Lake and the... read more

With a wide array of homes and an innovative sense of style, Taylor-Made Deep Creek Vacations & Sales invites you to stay in a opulent rental and experience the majestic beauty of Deep Creek Lake and the surrounding mountains. You'll swear your rental was tailor made for you!

Bad puns aside, Taylor-Made offers properties that are surrounded by four seasons of activities and adventure, so good that you'll want to come back just to experience it all! Go rent a jet ski for some high-speed excitement, or grab a boat and take a fishing tour with one of the local guides. Tackle the rapids at the Adventure Sports Center's man made white water rafting course or brave some of the nation's top rivers with local rafting companies. Winter allows for skiing, snowboarding, ice skating and more! Go have a blast, then when you're all tuckered out return to your exceedingly cozy home.

Address

35 Towne Centre Way, McHenry, MD 21541

Total area

Deep Creek Lake covers approximately 3,900 acres and has 69 miles of shoreline.

Fun facts

Deep Creek Lake is the largest inland body of water in Maryland

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8

Vacasa Vacation Rentals Ocean City

Ocean City, Maryland

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+1 (503) 345 - 9399

Whether you're a family looking to make some memories or a couple in need of a romantic escape, you'll find what you're looking for in a Vacasa Rental!Make yourself cozy inside a spacious Vacasa Vacation Rental!... read more

Whether you're a family looking to make some memories or a couple in need of a romantic escape, you'll find what you're looking for in a Vacasa Rental!

Make yourself cozy inside a spacious Vacasa Vacation Rental! You'll feel like royalty surrounded by such opulence, from the exquisite furnishings and grandiose full kitchens to the stately deck's which enjoy majestic beach views. Of course, the accommodations are simply the means to an end- that being the oodles of attractions and activities Ocean City provides! There are miles of pristine beach and a wooden boardwalk lined with a variety of restaurants and shops perfect for a lazy afternoon. Spend a day at the beach, grabbing a tan or splashing about in the crystal clear water- there's no wrong way to enjoy yourself at Vacasa!

Population

The town supports a year-round population of about 8,000.

Highlights

Ocean City also has a public transportation system referred to as the "Beach Bus" which runs along pretty much the entire length of the city, 24 hours a day, 7 days a week.

Fun facts

Prior to 1870, what is now Ocean City was known as "The Ladies' Resort to the Ocean."

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9

Eastern Shore Vacation Rentals

Easton, Maryland

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+1 (410) 770 - 9093

Eastern Shore Vacation Rentals' properties are scattered throughout many of Maryland's most charming towns, including St. Michaels, Easton, Oxford, Tilghman Island, Cambridge, and Chestertown. Why not try them... read more

Eastern Shore Vacation Rentals' properties are scattered throughout many of Maryland's most charming towns, including St. Michaels, Easton, Oxford, Tilghman Island, Cambridge, and Chestertown. Why not try them all?

The quiet Maryland Eastern Shore is the perfect place to escape the hustle and bustle of a typical beach vacation, and instead surround yourself with serenity and natural beauty. Sunrises and sunsets, miles of pristine shoreline, sophisticated small town charm and family friendly fun are just SOME of the reasons that families return year after year, but it's Eastern Shore's incredible hospitality that truly seals the deal. Right outside of your exquisitely cozy rental you'll have an entire world of fun at your fingertips. Go fishing, crabbing, golfing, sailing, swimming, kayaking or biking, or do it all! Or, slow it down and absorb the breathtaking views from your secluded dock and relax in your own private pool.

Address

16 N. Washington St. Suite 102, Easton, Maryland 21601

Highlights

Most homes are dog friendly, so you don't have to leave your best friend behind!

Fun facts

St. Michaels is consistently named as a top vacation destination by travel media!

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10

Offlake Realty & Rentals

Oakland, Maryland

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+1 (877) 389 - 9740

Picture yourself lounging on a patio, listening to waves gently lap against the shore and a cacophony of cicadas while you flip through a good book. That's just a typical day at an Offlake Realty & Rentals... read more

Picture yourself lounging on a patio, listening to waves gently lap against the shore and a cacophony of cicadas while you flip through a good book. That's just a typical day at an Offlake Realty & Rentals property.

With a wide selection of accommodations just steps away from the shores of beautiful Deep Creek Lake, Offlake Realty & Rentals features everything you need for a comfortable and convenient vacation. From their fully-equipped kitchens and spacious living rooms to hot tubs and super fast Wi-Fi, it's a Maryland vacationer's paradise. Away from your rental, you'll find that the Deep Creek area is chock-full of things to do, see, and experience. Get out on the lake for some fishing, lounge under the sun on the beach, or take a short drive and experience the variety of golf courses, nearby state and national parks, and local shops and restaurants nearby!

Address

12978 Garrett Hwy, Oakland, MD 21550

Population

The town has a population of 1,925 according to the 2010 United States Census.

Related activities

Oakland is situated only miles from the source of the Potomac River, which flows directly into the Chesapeake Bay.

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11

Railey Vacations

McHenry, Maryland

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+1 (866) 820 - 6268

Don't let Deep Creek Lake's name fool you- it's much more than a creek. It's actually one of the largest and most beautiful lakes in a ll of Maryland, and companies have sought to cash in on its appeal for decades.... read more

Don't let Deep Creek Lake's name fool you- it's much more than a creek. It's actually one of the largest and most beautiful lakes in a ll of Maryland, and companies have sought to cash in on its appeal for decades. Railey Mountain Lake Vacations, however, does this better than the rest.

With over 450 rental houses, condos, cottages,and cabins, Railey Mountain Lake Vacations is the top provider of rentals in the Deep Creek Lake area. What can you expect when you stay in one of these comfortable properties? Firstly, a wide selection of features and amenities, from private pools and hot tubs, to home theaters, game rooms and cozy fireplaces. Secondly, an incredible location. Some properties are even located right on the lake, while others are nestled in the woods in a more private setting. And third, you can expect an easy, intuitive process when booking. Their website offers easy and efficient online booking, and allows you to search by home size and property features, and then view photos of the homes of your dreams.

Address

5 Vacation Way, McHenry, MD 21541

Getting there

Deep Creek Lake is just a short drive from D.C., Baltimore, Fairfax, and Pittsburgh!

Fun facts

Railey Mountain Lake Vacations has the largest selection of rental homes at Deep Creek Lake!

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Chesapeake Hospitality

Address

Population

Fun facts

Tidewater Vacations

Address

Highlights

Fun facts

7C's Lodging

Address

Highlights

Getting there

Yellowstone Villages

Address

Highlights

Related activities

Central Reservations

Address

Population

Related activities

Century 21 New Horizon

Address

Highlights

Fun facts

Taylor-Made Deep Creek Vacations & Sales

Address

Total area

Fun facts

Vacasa Vacation Rentals Ocean City

Population

Highlights

Fun facts

Eastern Shore Vacation Rentals

Address

Highlights

Fun facts

Offlake Realty & Rentals

Address

Population

Related activities

Railey Vacations

Address

Getting there

Fun facts

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