Search vacation rentals in Maryland from 100+ sites!

57371 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Maryland vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Maryland

Best family friendly Maryland vacation rentals

Among the 57371 accommodations in Maryland, here are the 4 best family friendly rentals

Turf Valley Resort - Maryland
8.9 1976 reviews
Maryland
08/15 – 08/17
$187/nighttotal: $374 (2 )

Turf Valley Resort

1 2
resort , Ellicott City
Turf Valley Resort is located near historic downtown Ellicott City, just off Interstate 70, making it a convenient base for exploring Baltimore and Washington, D.C. This resort has received very good ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodations, including spacious rooms and suites with modern amenities. Guests can enjoy a variety of amenities, including two championship golf courses, a full-service spa, a fitness center, tennis courts, and indoor and outdoor pools.
Equestrian Escape! Quiet Farm Stay Near Gettysburg - Maryland
9.8 103 reviews
Maryland
07/11 – 07/16
$209/nighttotal: $1045 (5 )

Equestrian Escape! Quiet Farm Stay Near Gettysburg

1 4
house , Union Bridge
This charming house is located in Keymar, Maryland, just a short drive from historical attractions like Little Round Top Gettysburg and Devil’s Den Gettysburg, offering a peaceful escape from the city. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The home has one bedroom and one bathroom, accommodating up to four guests, and offers a spacious 1190 square feet of living space. Guests can enjoy a fully equipped kitchen, a private patio, and access to the horse breeding farm, providing a unique rural experience.
A Private And Peaceful Oasis With All Amenities In Quiet Scenic Brookeville - Maryland
9.2 5 reviews
Maryland
06/27 – 07/06
$175/nighttotal: $1575 (9 )

A Private And Peaceful Oasis With All Amenities In Quiet Scenic Brookeville

1 1
apartment , Olney
This Brookeville apartment rental is conveniently located within 6 miles of Patuxent River State Park, MedStar Montgomery Medical Center, and the Olney Theatre Center, offering easy access to outdoor recreation and cultural attractions.
The one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with microwave and dishwasher, in-unit laundry, a fireplace, a private patio, and a Smart TV; barbecue grills are available on-site.
Riverside At Pear Tree Point--waterfront Escape - Maryland
Maryland
07/06 – 07/11
$432/nighttotal: $2160 (5 )

Riverside At Pear Tree Point--waterfront Escape

3 10
apartment , Kingstown
This waterfront house in Pear Tree Point, Kingstown offers direct river views and is a short drive from the shops and restaurants of historic Chestertown, Maryland, with sports courts less than 0.5 miles away.
This family-friendly residence accommodates up to 10 guests with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a terrace/balcony, a garden, and a walkout lower level featuring a second family room with bunk beds.

Top cities

Best pet friendly Maryland vacation rentals

Among the 57371 accommodations in Maryland, here are the 4 best pet friendly rentals

Cute Bungalow Blocks To Stadium - Maryland
9.8 8 reviews
Maryland
06/20 – 06/27
$508/nighttotal: $3556 (7 )

Cute Bungalow Blocks To Stadium

2 2
apartment , Annapolis
This Annapolis vacation home, located in the Admiral Heights neighborhood, is 0.5 miles from People's Brewer Hill Cemetery and 1.6 miles from the U.S. Naval Academy.
This 1190-square-foot rental boasts three bedrooms, two bathrooms, a private garden with barbecue grills, and accommodates up to six guests with amenities including a fully equipped kitchen, balcony, and free internet.
Charming "Cream Of The Crop" Cape ~️Of Middletown - Maryland
9.9 456 reviews
Maryland
10/02 – 10/04
$272/nighttotal: $544 (2 )

Charming "Cream Of The Crop" Cape ~️Of Middletown

2 2
apartment , Middletown
This Middletown vacation home is conveniently located just 2.5 miles from Orchid Cellar Winery and within a 6-mile radius of several other attractions including wineries, a state park, and two golf courses. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall user experience.
This 1400 square foot home features two bedrooms and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen, a fireplace, outdoor patio with barbecue grills, a washing machine, and modern conveniences like a refrigerator and TV.
⋘ Lakeside Apartment ⋙| Private+cozy Setting | - Maryland
9.6 75 reviews
Maryland
07/01 – 11/30
$94/nighttotal: $14288 (152 )

⋘ Lakeside Apartment ⋙| Private+cozy Setting |

1 1
apartment , Queenstown
This one-bedroom apartment is located in historic Wye Mills, Maryland, on 17 private acres with access to a lake and just a short drive from Chesapeake College. It has received excellent ratings for cleanliness, location, and overall guest experience.
The rental has one bedroom and one bathroom, comfortably accommodating up to 5 guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, parking, and high-speed internet, along with access to a lake for kayaking, fishing, and other water activities.
Easy Metro Access: Wfh-friendly Apt 7 Mi To Dc! - Maryland
8.6 4 reviews
Maryland
06/20 – 06/27
$123/nighttotal: $861 (7 )

Easy Metro Access: Wfh-friendly Apt 7 Mi To Dc!

1 2
apartment , Silver Spring
This Silver Spring condo is located 0.9 miles from the Baltimore & Ohio Railroad Station and within 3.1 miles of Rock Creek Park and Holy Cross Hospital.
This pet-friendly rental offers complimentary WiFi in public areas, free self-parking, an in-unit microwave, and a coffee/tea maker.

Frequently Asked Questions about vacation rentals in Maryland

  • What are the must-see sights in Maryland?

    Maryland offers a diverse range of attractions. For history buffs, a visit to the Inner Harbor in Baltimore, with its maritime museums and the National Aquarium, is a must. Historic Annapolis, the state capital, boasts charming architecture and the United States Naval Academy. For a glimpse into colonial life, explore the St. Mary's City historic site. Don't forget the charming Eastern Shore towns like St. Michaels.
  • What are the best Airbnb and vacation rentals in Maryland?

  • Are there unique natural phenomena in Maryland?

    Yes! Assateague Island National Seashore, known for its wild horses, offers stunning beaches and wildlife viewing opportunities. The Chesapeake Bay, the largest estuary in the United States, provides incredible opportunities for boating, fishing, and birdwatching. Deep Creek Lake in Western Maryland is a popular destination for outdoor recreation.
  • What are the most popular Airbnbs in Maryland?

  • What essentials should you bring along for a trip to Maryland?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring. Depending on the time of year, layers of clothing are recommended, as Maryland's weather can be unpredictable. Sunscreen, insect repellent, and a reusable water bottle are also essential, especially during warmer months. Don't forget your camera to capture the beautiful scenery!
  • What are the best vacation rentals with a pool in Maryland?

    Unit 9 Ocean Side 41 St 50 Steps To The Beach, Lovely 2b/2b Belmont Towers and Belmont Towers 801 are the best vacation rentals with a pool in Maryland.

  • What famous events or festivals are happening in Maryland?

    Maryland hosts many events throughout the year. The Preakness Stakes, a renowned thoroughbred horse race, takes place in Baltimore. The Maryland Renaissance Festival offers a unique experience with medieval-themed activities. Numerous smaller festivals and events happen throughout the state, celebrating local culture and produce.
  • What are the best rentals for families and kids in Maryland?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Maryland?

    A daily budget will vary greatly depending on your travel style. For a budget-conscious trip, you could plan for around $100-$150 per day, covering budget-friendly accommodations, meals, and some activities. A mid-range budget might be $200-$300 per day, allowing for more comfortable lodging and dining options. Luxury travel could easily exceed $500 per day.
  • What are the best rentals or Airbnbs with a jacuzzi in Maryland?

  • Where can you find the best restaurants serving local dishes in Maryland, and what are the must-try specialties?

    Baltimore's Inner Harbor offers many seafood restaurants. Crab cakes are a Maryland staple, and you'll find countless variations throughout the state. Smith Island Cake, a unique layered dessert, is another must-try. Exploring smaller towns along the Eastern Shore will reveal charming restaurants serving fresh, local seafood and produce.
  • What are some less-famous attractions in Maryland that are worth a visit?

    Consider visiting the Catoctin Mountain Park, offering hiking trails and scenic views. The Chesapeake & Ohio Canal National Historical Park provides a peaceful escape with opportunities for biking and walking along the canal towpath. The Harriet Tubman Underground Railroad State Park offers a powerful and moving historical experience.
  • What are the best activities for engaging with locals and understanding their culture in Maryland?

    Visiting local farmers' markets provides a chance to interact with local producers and sample regional specialties. Attending smaller, community-based festivals and events offers opportunities to meet residents and experience local traditions. Exploring the state's many historical sites can provide insight into Maryland's rich history and culture.
  • What unique natural landscapes and terrain features can travelers explore in Maryland?

    Maryland boasts diverse landscapes. The Chesapeake Bay offers a unique estuary environment. The mountains of Western Maryland provide opportunities for hiking and scenic drives. The coastal plains of the Eastern Shore offer beautiful beaches and farmland. The Piedmont region offers rolling hills and forests.
  • How many days are ideal for visiting Maryland, and what are some itinerary suggestions?

    A long weekend (3-4 days) allows for exploring a specific region, such as Baltimore and Annapolis. A week-long trip allows for a more comprehensive experience, including both city and nature destinations. Two weeks would allow for a thorough exploration of the entire state. Itinerary suggestions would depend on your interests and the length of your stay.

Nearby regions

Best Maryland vacation rentals with a pool

Among the 57371 accommodations in Maryland, here are the 4 best rentals with a pool

Leeds Landing - Maryland
Maryland
07/13 – 07/18
$1174/nighttotal: $5870 (5 )

Leeds Landing

1 8
house , Easton
This Easton-area vacation home, Leeds Landing, is located in Saint Michaels, Maryland, seven miles from the Academy of the Arts and 25 miles from the Chesapeake Exploration Center.
This 2,560-square-foot house features four bedrooms, three bathrooms, a private pool, free Wi-Fi, free parking, and a fully equipped kitchen, comfortably accommodating up to 19 guests.
3 Bedroom W Indoor Pool Hotub - Maryland
8.6 11 reviews
Maryland
07/19 – 07/25
$338/nighttotal: $2028 (6 )

3 Bedroom W Indoor Pool Hotub

3 4
house , Wheaton
This Wheaton house rental, located in the suburbs approximately 9 miles from the Phillips Collection in Silver Spring and 10 miles from both the Walter E. Washington Convention Center and the White House, offers convenient access to Washington, D.C. attractions.
This three-bedroom, two-bathroom home sleeps up to 12 guests and boasts a private indoor pool and hot tub, a fully equipped kitchen, free Wi-Fi, free parking, and a terrace with garden views.
The Heron's Nest At Atlantic Marina - Maryland
9.8 315 reviews
Maryland
07/19 – 07/25
$375/nighttotal: $2250 (6 )

The Heron's Nest At Atlantic Marina

1 4
cottage , Lake Shore
This charming cottage is located in Pasadena, just steps from the beach on the Patapsco River, offering breathtaking water views and a peaceful escape. The cottage has consistently received excellent reviews from previous guests.
The cottage has a spacious layout with 580 square feet of living space, one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a private porch, and access to a swimming pool, making it perfect for families and groups seeking a relaxing getaway.
Luxe Houseboat: Breathtaking Skyline 360 Views - Maryland
10 24 reviews
Maryland
06/19 – 06/21
$1183/nighttotal: $2366 (2 )

Luxe Houseboat: Breathtaking Skyline 360 Views

1 2
houseboat , Baltimore
FLOHOM 1 | Bay Escape is a unique houseboat docked in Baltimore's Inner Harbor, offering stunning views of the city skyline and easy access to attractions like the National Aquarium and Camden Yards. This houseboat consistently receives excellent ratings from guests.
FLOHOM 1 | Bay Escape comfortably sleeps four guests in one bedroom and two bathrooms. This floating home comes with amenities like a fully equipped kitchen, air conditioning, a swimming pool, and a terrace, making it a perfect choice for a relaxing getaway.

Neighborhoods and points of interest in Maryland

Best Maryland vacation rentals with parking

5 Bedroom Home Near Downtown Annapolis - Maryland
Maryland
09/10 – 09/13
$803/nighttotal: $2409 (3 )

5 Bedroom Home Near Downtown Annapolis

5 12
house , Annapolis
This house is located near downtown Annapolis, offering convenient access to the city's attractions.
This 1800-square-foot home accommodates up to 23 guests with 2 bathrooms, a full kitchen, free WiFi, and private parking.
Cozy 1-bedroom & Loft Duplex In Pleasant Frederick With Ac - Maryland
Maryland
06/27 – 07/06
$52/nighttotal: $468 (9 )

Cozy 1-bedroom & Loft Duplex In Pleasant Frederick With Ac

1 1
apartment , Frederick
This one-bedroom apartment in Frederick is located near Regal Westview and Frederik Golf Club, with the Roads and Rails Museum and The Delaplaine Arts Center also within easy reach.
This pet-friendly rental offers air conditioning, a garden, parking, and a kitchen equipped with a fridge, microwave oven, and dishwasher, ideal for one guest.
Entire Private 2 Bedrooms House, Nice Neighborhood - Maryland
9.4 82 reviews
Maryland
10/02 – 10/04
$266/nighttotal: $532 (2 )

Entire Private 2 Bedrooms House, Nice Neighborhood

2 2
apartment , Arnold
This 2-bedroom house is located in Arnold, a quiet neighborhood about 10 miles from Annapolis Harbor and 14 miles from Baltimore-Washington International Airport. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The 1190 square foot apartment comfortably accommodates up to 5 guests. Enjoy the relaxing amenities like the hot tub, garden, and fully equipped kitchen with a dishwasher, oven, washing machine, microwave, and toaster.
Luxury Private Pass Time Space - Maryland
10 2 reviews
Maryland
09/01 – 11/30
$74/nighttotal: $6660 (90 )

Luxury Private Pass Time Space

2 2
apartment , Beltsville
This basement apartment in Beltsville offers convenient access to Washington D.C. attractions, located approximately 10 miles from the White House and Washington Monument, and within easy reach of the Smithsonian Institution and National Zoo.
This family-friendly rental features two bedrooms, a fully equipped kitchen, a separate dining and living room, dedicated office space, and unlimited parking, accommodating up to five guests.
©2026 cozycozy.com