Best Vacation Homes in Maryland
Cabin
10.0(398 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
Hot Tub
Spa
Fireplace/Heating
Pool
CA $759/Night
7 Nights - CA $5,313
Bed & Breakfast
10.0(99 Reviews)
12 Bedrooms
12 Baths
26 Guests
260.13 ft²
Private Beach
Oceanfront- Hot Tub
Ocean View
CA $412/Night
7 Nights - CA $2,881
Bed & Breakfast
10.0(223 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Fireplace/Heating
Balcony/Terrace
Breakfast
CA $375/Night
7 Nights - CA $2,621
House
10.0(392 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Kitchen
Parking
CA $437/Night
7 Nights - CA $3,058
Bed & Breakfast
10.0(89 Reviews)
23 Bedrooms
24 Baths
60 Guests
- Balcony/Terrace
- Parking
Air Conditioner
Internet
CA $399/Night
7 Nights - CA $2,793
Cabin
10.0(237 Reviews)
1 Bedroom
1 Bath
4 Guests
840 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
CA $216/Night
7 Nights - CA $1,515
House
10.0(198 Reviews)
3 Bedrooms
2 Baths
10 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $613/Night
7 Nights - CA $4,293
Cottage
10.0(161 Reviews)
2 Bedrooms
1 Bath
6 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
CA $268/Night
7 Nights - CA $1,878
Maryland Luxury Rentals
House
12 Bedrooms
12 Baths
24 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
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House
12 Bedrooms
1 Bath
24 Guests
204.51 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
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House
25 Bedrooms
20 Baths
40 Guests
11000.72 ft²
- Fireplace/Heating
- Pool
- View
- Parking
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House
7 Bedrooms
7 Baths
30 Guests
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
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House
5 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
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House
3 Bedrooms
2 Baths
1 Guest
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
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Condo
6.0(1 Review)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
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Condo
2 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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Maryland Pet Friendly Vacation Rentals
Cottage
10.0(147 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,205/Night
7 Nights - CA $8,433
House
10.0(9 Reviews)
4 Bedrooms
3 Baths
12 Guests
2195.84 ft²
- Oceanfront
- Hot Tub
- Spa
Skiing
CA $414/Night
7 Nights - CA $2,900
Bed & Breakfast
10.0(89 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
CA $500/Night
7 Nights - CA $3,498
Cottage
10.0(84 Reviews)
2 Bedrooms
1 Bath
5 Guests
576 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $373/Night
7 Nights - CA $2,608
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
10 Guests
10763.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
CA $1,369/Night
7 Nights - CA $9,581
Cottage
10.0(67 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $1,152/Night
7 Nights - CA $8,066
House
10.0(62 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $382/Night
7 Nights - CA $2,671
House
10.0(53 Reviews)
2 Bedrooms
1 Bath
4 Guests
1 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $416/Night
7 Nights - CA $2,911
Maryland Large Vacation Homes
Villa
10.0(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $570/Night
7 Nights - CA $3,990
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- Skiing
- Fireplace/Heating
- Parking
- Air Conditioner
CA $1,117/Night
7 Nights - CA $7,817
Condo
8.4(19 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
CA $702/Night
7 Nights - CA $4,915
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $359/Night
7 Nights - CA $2,511
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
2594.1 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
CA $893/Night
7 Nights - CA $6,248
CA $1,659/Night
7 Nights - CA $11,613
House
8.4(5 Reviews)
2 Bedrooms
3 Baths
10 Guests
1536 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
CA $346/Night
7 Nights - CA $2,424
House
8.0(43 Reviews)
2 Bedrooms
3 Baths
10 Guests
1536 ft²
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
CA $342/Night
7 Nights - CA $2,392
Why Choose Rent By Owner for your Maryland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Maryland
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit ensures you experience the region’s best weather and attractions, making your stay in Maryland perfect for relaxing or exploring at your own pace.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, the area experiences warm weather ideal for exploring outdoors and enjoying the natural beauty of Maryland.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Early Fall (September to October)
The region offers mild temperatures and vibrant foliage, making it a perfect time for outdoor activities and sightseeing.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
This quieter season features cooler temperatures, providing a peaceful atmosphere for those seeking tranquility away from the crowds.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Early Spring (March to April)
As the weather begins to warm, fewer visitors explore the area, making it an ideal choice for budget-conscious travelers seeking a calm getaway.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Maryland
How to Book Your Maryland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Maryland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool for refreshing swims during your stay in the region.
- Relax on spacious decks or patios equipped for outdoor dining and entertaining.
- Take advantage of lush, landscaped gardens that enhance the natural beauty of your surroundings.
- Make use of outdoor grills for cooking up delicious meals while enjoying the fresh air.
- Explore extensive grounds with walking trails perfect for nature walks and exploration.
- Set up outdoor recreation areas such as volleyball courts or basketball hoops for active fun.
- Benefit from waterfront access or scenic views that highlight the area's natural charm.
Top Attractions Around Maryland
What attractions are nearby?
While staying in Maryland, you can explore a variety of nearby activities ranging from scenic outdoor adventures to cultural experiences, all conveniently accessible from your chosen vacation rental here in this vibrant region.
Family Activities
- National Aquarium in Baltimore: Discover marine life through interactive exhibits and mesmerizing aquariums, making it a perfect family activity in this region.
- Fort McHenry National Monument and Historic Shrine: Explore the historic fort where you can learn about American history while enjoying outdoor picnics and scenic views.
- Deep Creek Lake State Park: Enjoy outdoor adventures such as boating, fishing, and hiking at this popular destination for family fun in the area's natural setting.
- Six Flags America: Experience thrilling rides and entertaining shows suitable for all ages at this exciting amusement park within the local region.
Adult Activities
- Explore the Chesapeake Bay Maritime Museum: Discover the area's rich maritime history and enjoy hands-on exhibits that bring the region's naval traditions to life.
- Visit historic Annapolis: Stroll through the charming streets of this coastal city, taking in colonial architecture and vibrant waterfront views that showcase Maryland's heritage.
- Enjoy outdoor adventures in Patapsco Valley State Park: Engage in hiking, biking, or picnicking amidst lush scenery that highlights the natural beauty of this destination.
- Tour local vineyards and wineries: Experience tastings at some of the region's renowned vineyards, offering a taste of Maryland's growing wine country.
Other Places to Stay in Maryland, MD
Chesapeake Bay
Northern Chesapeake Bay
Worcester County
Ocean City
Cumberland
Garrett County
North Ocean City
Midtown Ocean City
Anne Arundel County
McHenry
Baltimore
Isle of Wight Bay
Maryland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the area's renowned cultural and outdoor sites to fully immerse yourself in the region's unique charm.
- Plan Your Transportation: Consider convenient transportation options within the destination to easily access key attractions and maximize your stay.
- Choose a Well-Located Property: Select vacation rentals that are centrally situated to minimize travel time and provide easy access to popular destinations in this area.
- Discover Regional Cuisine: Savor the local flavors by exploring nearby restaurants or preparing meals in your rental, enhancing your authentic experience here.
Transportation Options
- Maryland Transit Administration (MTA): The MTA offers extensive bus and light rail services that make exploring the area convenient for visitors staying in vacation rentals.
- Amtrak: Connecting you to major cities along the East Coast, Amtrak provides seamless train travel options for your stay here.
- Baltimore/Washington International Thurgood Marshall Airport (BWI): As a primary airport hub, BWI is an accessible option for travelers arriving from various locations around the country.
- Car Rentals: Renting a vehicle allows for flexible exploration of this destination and the surrounding region at your own pace.
Local Customs Options
- Crab Feast Culture: Participating in a traditional crab feast is a cherished tradition here, offering a flavorful glimpse into local culinary customs.
- Fishing and Boating Etiquette: Respect for water activities, such as fishing and boating, reflects the region’s maritime heritage and is highly valued by locals.
- Decorative Arts and Crafts: Appreciating Maryland's unique craft traditions, like quilt-making and glasswork, allows you to connect with the area's artisanal customs.
- Historical Preservation Practices: Embracing respect for historical sites and participating in community restoration efforts showcase the area’s dedication to preserving its rich history.
Frequently Asked Questions About Maryland?
1. 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:
- Lakefront Cabin, Finnish Sauna, Kayaks, Dock, Hot Tub, Gardens - OWLS NEST, DCL
- Stay in the HEART of Saint Michaels!
- #1 Rated Condo, Oceanfront, with Bay View Too
- Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Captivating Chesapeake experience
- Family and Pet-Friendly, Waterfront with Pier
- Annapolis waterfront "tiny house" in garden setting
- Oceanfront and Boardwalk luxury condo - 705
- Bayfront Penthouse Amazing views and a Pool. Walk to Boardwalk and Beach.
2. How many vacation rentals have private pools in Maryland?
There are 1495 vacation rentals with private pools near Maryland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Maryland are best for families?
If you are looking for a family-friendly vacation home in Maryland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Maryland:
4. How many Rentbyowner vacation rentals are available in Maryland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 27206 in the Maryland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Maryland.
5. What is the cancellation policy for vacation rentals in Maryland?
Cancellation policies vary by listing, so it’s important to review the specific terms on each property's page. Some may offer flexible cancellation options, while others might have stricter policies. Contact the host directly if you need clarification.
6. How do I ensure my reservation in Maryland is secure and trustworthy?
All listings on the platform are verified for quality and safety. To further ensure your reservation's security, communicate through the official messaging system and only make payments via the platform's trusted methods.
7. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning, service charges, or taxes are often included in the total price listed. Always review the detailed fee breakdown before completing your booking to avoid surprises.
8. Can I modify or cancel my reservation if my plans change?
Yes, many listings allow modifications or cancellations based on the property's policy. However, terms can differ, so it's best to check the specific cancellation and modification policies on the property details page or contact the host directly.
9. What amenities can I expect from vacation rentals here in Maryland?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. Review each listing carefully to find accommodations that meet your needs and preferences during your stay in the region.
Maryland Top Rated Vacation Rentals
Condo
10.0(331 Reviews)
2 Bedrooms
1 Bath
6 Guests
990 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $308/Night
7 Nights - CA $2,155
House
10.0(312 Reviews)
4 Bedrooms
2 Baths
14 Guests
2240 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $439/Night
7 Nights - CA $3,070
Cottage
10.0(267 Reviews)
4 Bedrooms
1 Bath
8 Guests
1872 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $523/Night
7 Nights - CA $3,660
Condo
10.0(252 Reviews)
3 Bedrooms
3 Baths
8 Guests
1750 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
CA $746/Night
7 Nights - CA $5,225
Condo
10.0(249 Reviews)
4 Bedrooms
3 Baths
10 Guests
1950 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $947/Night
7 Nights - CA $6,632
House
10.0(222 Reviews)
2 Bedrooms
1 Bath
6 Guests
750 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $656/Night
7 Nights - CA $4,592
Cabin
10.0(218 Reviews)
3 Bedrooms
2 Baths
13 Guests
1440 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $638/Night
7 Nights - CA $4,464
House
10.0(213 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
CA $549/Night
7 Nights - CA $3,844
