1623+ Vacation Rentals Near Maryland |
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Unplugged Weekend - Vacation Rentals in Maryland

Ocean Front, North Ocean City, Maryland in Ocean City From US $566
         

9.8 (48 Reviews)
Condo
Ocean Front, North Ocean City, Maryland
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Foxfire - Secluded Zen Retreat with Spa & Views in Smithsburg From US $342
         

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10.0 (9 Reviews)
House
Foxfire - Secluded Zen Retreat with Spa & Views
  • Air Conditioner
  • Parking
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Blackwater Bend - Waterfront Farm w/Pool & Dock - Sleeps 10 in Cambridge From US $676
         

New
House
Blackwater Bend - Waterfront Farm w/Pool & Dock - Sleeps 10
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⛱️2BR/2BA OCEANFRONT BUILDING. Book End of Summer/FALL Rates AS LOW AS $99/Night in Ocean City From US $223
         

10.0 (140 Reviews)
Condo
⛱️2BR/2BA OCEANFRONT BUILDING. Book End of Summer/FALL Rates AS LOW AS $99/Night
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Capri Ocean Front Family Beach Vacation Resort in Ocean City From US $391
         

10.0 (49 Reviews)
Condo
Capri Ocean Front Family Beach Vacation Resort
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Gorgeous Direct Oceanfront in Ocean City From US $107
         

9.8 (38 Reviews)
Condo
Gorgeous Direct Oceanfront
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DIRECT OCEANFRONT VIEW CALL HOST NOW FOR DISCOUNTS FOR AUG SEPT OCT FREE LINENS in Ocean City From US $366
         

9.8 (26 Reviews)
Condo
DIRECT OCEANFRONT VIEW CALL HOST NOW FOR DISCOUNTS FOR AUG SEPT OCT FREE LINENS
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Nicely Appointed Beachfront Condo with Incredible Views and Indoor Pool! in Ocean City From US $306
         

9.4 (175 Reviews)
Condo
Nicely Appointed Beachfront Condo with Incredible Views and Indoor Pool!
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  • Pool

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Luxury Places to Stay in Maryland

Over 10000+ Luxury Places to Stay in or Near Maryland
New
House
Luxury Estate for Filming
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  • Pet Friendly
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Luxury Estate for Filming
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New
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25 Bedrooms - Retreat Center Waterfront Renovated
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Moofy's Farmhouse: Main Lodge ; Private Waterfront Retreat Center, New Reno on 18 Acres
  • Air Conditioner
  • Parking
  • Pool

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New
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Spacious 7-bedroom house in tranquil Fallston with fitness room, AC
  • Air Conditioner
  • Parking
  • Pet Friendly

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6.0 (1 Review)
Condo
Tiffanie by the Sea 319D-Oceanside 55th St, W/D, AC
  • Parking
  • Pool
  • TV

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New
House
Walk to Harborside Sleeps 16 Boat Trailer Parking
  • Air Conditioner
  • Parking
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New
House
Townhouse near to Towson center and Parkville, EV charger available.
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Top-Rated Vacation Rentals with a Pool in Maryland

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Maryland
Island Life! Kent Island Waterfront with Pool-Bring your boat! in Stevensville From US $581
         

10.0 (214 Reviews)
House
Island Life! Kent Island Waterfront with Pool-Bring your boat!
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BOAT, FISH, CRAB, SWIM, RELAX! WELCOME TO YOUR EASTERN SHORE ESCAPE! in Cambridge From US $484
         

10.0 (213 Reviews)
House
BOAT, FISH, CRAB, SWIM, RELAX! WELCOME TO YOUR EASTERN SHORE ESCAPE!
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5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip in Ocean City From US $860
         

10.0 (204 Reviews)
House
5-6BR, 5BA in Bayside Retreat with Community Pools & Boat Slip
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Waterfront Cabin with Million Dollar View and Luxury Bath! Find Shark's Teeth! in Port Republic From US $206
         

10.0 (199 Reviews)
House
Waterfront Cabin with Million Dollar View and Luxury Bath! Find Shark's Teeth!
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Beach Oceanfront~2BR/2BA~4 Seasons Availability~5 Star~Pool~Uptown~Booking 2027 in Ocean City From US $315
         

10.0 (182 Reviews)
Condo
Beach Oceanfront~2BR/2BA~4 Seasons Availability~5 Star~Pool~Uptown~Booking 2027
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Bay Front Condo w/Pool One Block from the Beach! in Ocean City From US $168
         

10.0 (169 Reviews)
Condo
Bay Front Condo w/Pool One Block from the Beach!
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St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3 in St. Michaels From US $867
         

10.0 (153 Reviews)
Cottage
St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3
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Huge Oceanfront Balcony | 3BR | 2 King Rooms | Pool | Perfect spot for families! in Ocean City From US $252
         

10.0 (151 Reviews)
Condo
Huge Oceanfront Balcony | 3BR | 2 King Rooms | Pool | Perfect spot for families!
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Pet-Friendly Vacation Rentals in Maryland

Over 5468+ Pet-Friendly Vacation Rentals in or Near Maryland
240' Private Beachfront @Kent Island Love Point - Great for Families in stevensville From US $678
         

10.0 (209 Reviews)
House
240' Private Beachfront @Kent Island Love Point - Great for Families
  • Air Conditioner
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  • Pet Friendly

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10 Clarke in Frederick From US $303
         

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9.7 (58 Reviews)
Bed & Breakfast
10 Clarke
  • Air Conditioner
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  • Pet Friendly

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Penthouse Retreat with Rooftop Pool – Explore Silver Spring & Washington D.C. in Silver Spring From US $362
         

9.8 (6 Reviews)
Apartment
Penthouse Retreat with Rooftop Pool – Explore Silver Spring & Washington D.C.
  • Air Conditioner
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  • Pet Friendly

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Eastern Shore beach cottage get-away in Rock Hall From US $457
         

10.0 (142 Reviews)
Cottage
Eastern Shore beach cottage get-away
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  • Parking
  • Pet Friendly

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Historic 70-Acre Farm with Porches, Animals & Ponds in Ijamsville From US $771
         

10.0 (110 Reviews)
House
Historic 70-Acre Farm with Porches, Animals & Ponds
  • Air Conditioner
  • Parking
  • Pet Friendly

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Kingsbay Mansion Bayhouse in Marion From US $943
         

10.0 (42 Reviews)
House
Kingsbay Mansion Bayhouse
  • Air Conditioner
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  • Pet Friendly

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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch in Saint Michaels From US $487
         

9.8 (208 Reviews)
Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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  • Pet Friendly

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Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW in Cambridge From US $669
         

9.8 (136 Reviews)
House
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
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  • Pet Friendly

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Large Vacation Homes & Villas in Maryland

Over 6429+ Large Vacation Homes & Villas in or Near Maryland
Luxury Home, 1.5mi to Assateague Island and Top Golf Courses! Sleeps 12! in Berlin From US $693
         

10.0 (103 Reviews)
House
Luxury Home, 1.5mi to Assateague Island and Top Golf Courses! Sleeps 12!
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Lake Pointe Inn in McHenry From US $337
         

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10.0 (99 Reviews)
Bed & Breakfast
Lake Pointe Inn
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Americana Condos 10th street in Ocean City From US $553
         

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8.4 (29 Reviews)
Condo
Americana Condos 10th street
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Baydream Believer in Talbot County From US $1,168
         

10.0 (88 Reviews)
House
Baydream Believer
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Family-Friendly Waterfront Retreat w/Pool, Dock, Firepit & Game Room in Cambridge From US $749
         

10.0 (74 Reviews)
House
Family-Friendly Waterfront Retreat w/Pool, Dock, Firepit & Game Room
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Huge 5 Bedroom, 4 bathrooms/Ocean Views/Open July 10-17, 2026 in Ocean City From US $583
         

10.0 (40 Reviews)
House
Huge 5 Bedroom, 4 bathrooms/Ocean Views/Open July 10-17, 2026
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🏖️ 5 Bedroom Penthouse Ocean Views, Renovated, Pool, Stunning Ocean Views🏖️ in Ocean City From US $383
         

9.8 (94 Reviews)
Condo
🏖️ 5 Bedroom Penthouse Ocean Views, Renovated, Pool, Stunning Ocean Views🏖️
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Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks in Easton From US $1,256
         

10.0 (145 Reviews)
House
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
  • Air Conditioner
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Wheelchair Accessible Vacation Homes in Maryland

Over 7306+ Wheelchair Accessible Vacation Homes in or Near Maryland
Ocean Front 1st Floor walkout to 25'x50' deck on the Boardwalk/Beach at 4th St in Ocean City From US $441
         

10.0 (80 Reviews)
Condo
Ocean Front 1st Floor walkout to 25'x50' deck on the Boardwalk/Beach at 4th St
  • Air Conditioner
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Thunder Island 67B in Ocean City From US $151
         

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10.0 (1 Review)
Apartment
Thunder Island 67B
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The Oaks Waterfront in Easton From US $538
         

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10.0 (42 Reviews)
Bed & Breakfast
The Oaks Waterfront
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Direct Oceanfront, Mid-Town, Updated & Spacious 1st Floor - Walk off to Beach in Ocean City From US $291
         

10.0 (79 Reviews)
Condo
Direct Oceanfront, Mid-Town, Updated & Spacious 1st Floor - Walk off to Beach
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BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL! in Ocean City From US $260
         

9.8 (145 Reviews)
Condo
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
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🏖️Spectacular Spacious Ocean Front Condo on Boardwalk, this one you've got to see! 🏖️ in Ocean City From US $380
         

9.6 (100 Reviews)
Condo
🏖️Spectacular Spacious Ocean Front Condo on Boardwalk, this one you've got to see! 🏖️
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Time to plan for SUMMER! Sunset Island Condo-67th St in Ocean City From US $696
         

10.0 (69 Reviews)
Condo
Time to plan for SUMMER! Sunset Island Condo-67th St
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Dazzling Views Perfect Location Ocean Front with Pool Fabulous Balcony Sleeps 6 in Ocean city From US $255
         

9.8 (56 Reviews)
Condo
Dazzling Views Perfect Location Ocean Front with Pool Fabulous Balcony Sleeps 6
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Maryland Vacation Rentals and Airbnb Places to Stay Under $200

Over 5767+ Maryland Vacation Rentals and Airbnb Places to Stay Under $200
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool in Ocean Pines From US $161
         

9.0 (108 Reviews)
House
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool
  • Air Conditioner
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  • Pet Friendly

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Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes in Baltimore From US $137
         

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5.0 (1 Review)
Apartment
Designer Fashion Loft 1 Bedroom Apartment -Royalty Homes
  • Air Conditioner
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  • Internet

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Historic 1825 Chesapeake Farm Stay in St. Leonard From US $144
         

10.0 (1 Review)
Bed & Breakfast
Historic 1825 Chesapeake Farm Stay
  • Parking
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  • Ocean View

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Great bayfront location that is steps from the Convention Center in Ocean City From US $198
         

9.4 (37 Reviews)
Condo
Great bayfront location that is steps from the Convention Center
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XPLORIE ACTIVITIES & LINENS INCLUDED*! PANORAMIC VIEWS! Bahama Princess-Direct bayfront 2BR/2BA condo. in Ocean City From US $196
         

8.8 (8 Reviews)
Condo
XPLORIE ACTIVITIES & LINENS INCLUDED*! PANORAMIC VIEWS! Bahama Princess-Direct bayfront 2BR/2BA condo.
  • Air Conditioner
  • Pool
  • TV

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Clean, Comfortable 2 bedroom condo on bayside. Pool, Wifi in Ocean City From US $150
         

9.4 (49 Reviews)
Condo
Clean, Comfortable 2 bedroom condo on bayside. Pool, Wifi
  • Air Conditioner
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  • Pool

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Sharpsburg Retreat-Civil War Home Near Antietam Battlefield, C&O Canal Towpath in Sharpsburg From US $176
         

9.6 (210 Reviews)
House
Sharpsburg Retreat-Civil War Home Near Antietam Battlefield, C&O Canal Towpath
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Oceanfront midrise building conveniently located on 52 street, perfect for a family of 6 in Ocean City From US $196
         

8.8 (21 Reviews)
Condo
Oceanfront midrise building conveniently located on 52 street, perfect for a family of 6
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Instantly Bookable Vacation Homes in Maryland

Over 17327+ Instantly Bookable Vacation Homes in or Near Maryland
PERFECT LOCATION in the heart of history in Annapolis From US $533
         

10.0 (231 Reviews)
House
PERFECT LOCATION in the heart of history
  • Air Conditioner
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  • Balcony/Terrace

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Crab Cove On The Bay 208 in Ocean City From US $317
         

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New
Apartment
Crab Cove On The Bay 208
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Lovely spacious 3 BR Condo - 88th St - 100 feet to the beach in Ocean City From US $323
         

9.2 (103 Reviews)
Condo
Lovely spacious 3 BR Condo - 88th St - 100 feet to the beach
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Charming Historic Annapolis Home With Two Off-street Parking Places! in Annapolis From US $817
         

10.0 (215 Reviews)
House
Charming Historic Annapolis Home With Two Off-street Parking Places!
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AMAZING LOCATION! JUST STEPS FROM THE BEACH! MINI WEEKS AVAILABLE! in Ocean City From US $350
         

10.0 (104 Reviews)
Condo
AMAZING LOCATION! JUST STEPS FROM THE BEACH! MINI WEEKS AVAILABLE!
  • Air Conditioner
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Gorgeous Views, Direct Bayfront Condo in Ocean City From US $281
         

9.8 (51 Reviews)
Condo
Gorgeous Views, Direct Bayfront Condo
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Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location! in Ocean City From US $339
         

9.2 (128 Reviews)
Condo
Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!
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4BR/4BA~New Hot Tub~Pet Friendly~Minutes to Wisp~Private Bath for Each BR in McHenry From US $539
         

9.6 (175 Reviews)
House
4BR/4BA~New Hot Tub~Pet Friendly~Minutes to Wisp~Private Bath for Each BR
  • Parking
  • Pet Friendly
  • TV

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About Maryland Vacation Rentals

With more than 1623 Maryland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Unpluggedweekend and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Maryland.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Unpluggedweekend Maryland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Maryland. Places to stay near Maryland are 1029.59 ft² on average, with prices averaging US $453 a night.

Unpluggedweekend makes it easy and safe to find and compare vacation rentals in Maryland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Maryland

Type Count
Vacation Homes 333
Holiday Apartments 111
Hotels 51
Resorts 37
Cabin Rentals 16
Villas 14
B&B 11
Cottages 9
Ski Chalet Rentals 4
Others 2

Use these Quick Filters to Find a Vacation Rental in Maryland

★ Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Maryland.

Weather in Maryland

View the weather forecast for Maryland before booking your Maryland Vacation Rentals to confirm your best time to go.

December - February
High 55°F       Low 28°F
March - May
High 72°F       Low 34°F
June - August
High 88°F       Low 63°F
September - November
High 78°F       Low 35°F

Top Attractions Around Maryland, US

Unpluggedweekend offers a large selection of top attractions around Maryland. Research things to do on your vacation before you visit Maryland.


National Aquarium in Baltimore Ocean City Boardwalk Baltimore Cruise Terminal University of Maryland-College Park Johns Hopkins University Baltimore Convention Center Johns Hopkins Hospital Horseshoe Casino Baltimore Ocean City Beach Baltimore Inner Harbor Marina Arundel Mills Mall FedEx Field M&T Bank Stadium MGM National Harbor Oriole Park at Camden Yards Maryland Live Casino U.S. Naval Academy Deep Creek Lake Towson University Jolly Roger Amusement Park Maryland Beach Deep Creek Lake State Park Salisbury University Ripken Stadium Casino at Ocean Downs Maryland Zoo Six Flags America Merriweather Post Pavilion Wisp Resort Rocky Gap State Park

Other Places to Stay Near Maryland, US


Chesapeake Bay 14,661 Properties Northern Chesapeake Bay 8,979 Properties Worcester County 7,550 Properties Ocean City 7,509 Properties North Ocean City 3,256 Properties Cumberland 2,501 Properties Garrett County 2,439 Properties Midtown Ocean City 2,409 Properties Isle of Wight Bay 1,325 Properties Anne Arundel County 1,274 Properties Baltimore 1,260 Properties McHenry 1,082 Properties

Complexes around Maryland, US


Sea Watch Ocean City 890 Properties Thunder Island 37 Properties Wyndham National Harbor 64 Properties Enjoy Beauty The Chesapeake Bay 41 Properties Loft Oakland 37 Properties Bethesda 33 Properties Belmont Ocean 28 Properties Frederick 17 Properties Ocean Hideaway 22 Properties Club Ocean Villas 18 Properties Assateague Pointe Woc 17 Properties Prince George St Annapolis 6 Properties Hampton Inn 3 Properties Breakaway East 11 Properties Brexton Baltimore 8 Properties
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Maryland Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Maryland?

There are a lot of options in Maryland. If you plan on staying in the Maryland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Maryland:

How many vacation rentals are available in Maryland?

Currently, the total number of properties listed in 2026 is over 1623 in the Maryland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Maryland.