Maryland vacation rentals

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Best Maryland vacation rentals

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₪53 - ₪1,379₪1,379 - ₪2,705₪2,705 - ₪4,032₪4,032 - ₪5,358₪5,358+ per night

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Most recommended vacation rentals in Maryland

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1 Mi to Boardwalk: Convenient North Beach Apt! - Owings - Bedroom
1 Mi to Boardwalk: Convenient North Beach Apt!
Owings, MD, United States
Free Wi-Fi
Air Conditioning
₪618+
Check availability
The Cozy Crab- Your Charming Haven in Lovely North Beach! - North Beach - Bedroom
The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach, MD, United States
Air Conditioning
₪708+
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Waterfront Lux Cottage With Amazing Views Near DC - North Beach - Living room
Waterfront Lux Cottage With Amazing Views Near DC
North Beach, MD, United States
9.0Wonderful(4)
Parking
Free Wi-Fi
Air Conditioning
₪815+
Check availability
Guest Quarters at the Inn - 101 - North Beach - Bedroom
Guest Quarters at the Inn - 101
North Beach, MD, United States
9.7Wonderful(9)
Free Wi-Fi
Air Conditioning
₪822+
Check availability
Beachwalk Cottage - Charm By The Chesapeake Bay - North Beach
Beachwalk Cottage - Charm By The Chesapeake Bay
North Beach, MD, United States
9.4Wonderful(22)
Pet friendly
Air Conditioning
₪995+
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Cozy and quiet basement apartment pet friendly! - Pikesville - Bedroom
Cozy and quiet basement apartment pet friendly!
Pikesville, MD, United States
8.0Very good(2)
Free Wi-Fi
Air Conditioning
₪1,094+
Check availability
Cozy Home in Private Beach Community Close to City - Chesapeake Beach - Living room
Cozy Home in Private Beach Community Close to City
Chesapeake Beach, MD, United States
8.0Very good(1)
Air Conditioning
₪1,119+
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Adorable Beach Cottage with Hot Tub and Tropical Bar! - Chesapeake Beach - Balcony
Adorable Beach Cottage with Hot Tub and Tropical Bar!
Chesapeake Beach, MD, United States
8.6Very good(9)
Free Wi-Fi
Air Conditioning
₪1,126+
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Bahia Breeze - Beachfront Cottage - Chesapeake Beach
Bahia Breeze - Beachfront Cottage
Chesapeake Beach, MD, United States
8.0Very good(1)
Air Conditioning
₪1,433+
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Cozy Getaway - Breezy Point Beach & Marina - Chesapeake Beach - Living room
Cozy Getaway - Breezy Point Beach & Marina
Chesapeake Beach, MD, United States
9.3Wonderful(3)
Free Wi-Fi
Air Conditioning
₪1,480+
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Huge Beach Bungalow- Yard, Beach Pass, King Beds - North Beach - Building
Huge Beach Bungalow- Yard, Beach Pass, King Beds
North Beach, MD, United States
10Wonderful(18)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
₪1,563+
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Rising Sun Bay View Cottage - Chesapeake Beach - Living room
Rising Sun Bay View Cottage
Chesapeake Beach, MD, United States
Air Conditioning
₪2,044+
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Grasonville Home with Private Pool on the Water - Grasonville - Pool
Grasonville Home with Private Pool on the Water
Grasonville, MD, United States
9.7Wonderful(20)
Free Wi-Fi
Pool
Air Conditioning
₪2,301+
Check availability
Waterfront 4 BR home with private pier and boat dock - Grasonville - Living room
Waterfront 4 BR home with private pier and boat dock
Grasonville, MD, United States
10Wonderful(9)
Free Wi-Fi
Air Conditioning
₪3,146+
Check availability
Amazing Waterfront Destination For Romantic And Family Vacations - Chesapeake Beach
Amazing Waterfront Destination For Romantic And Family Vacations
Chesapeake Beach, MD, United States
Free Wi-Fi
Air Conditioning
₪3,554+
Check availability
Indoor pool and spa in contemporary French home secluded in surrounding woods - Chesapeake Beach - Bedroom
Indoor pool and spa in contemporary French home secluded in surrounding woods
Chesapeake Beach, MD, United States
10Wonderful(7)
Pool
Air Conditioning
₪3,631+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Maryland

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Maryland with confidence.

How early should you book a vacation rental in Maryland?

Book at least 72 days before your stay begins to get the best price for your Maryland vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
October
₪703
₪838
Cheapest month to stay with an average 26% drop in price.
Most expensive month to stay with an average 24% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Maryland vacation rental

FAQs when booking a vacation home in Maryland

  • What is the most popular vacation rental destination in Maryland?

    Based on KAYAK vacation rental searches, the most popular destination is Chesapeake Beach (100% of total searches to Maryland).

  • How much is a vacation rental in Maryland for tonight?

    In the last 72 hours, users have found Maryland vacation rentals for tonight for as low as ₪204. Search here for similar prices

  • How much is a vacation rental in Maryland for this weekend?

    In the last 72 hours, users have found Maryland vacation rentals for this weekend for as low as ₪216 per night. Search here for similar prices

  • What types of vacation rentals are available in Maryland?

    There are loads of different property types that you can make your vacation home in Maryland. You’ll find apartments, cottages, houses, homestays, houseboats, villas, bungalows, cabins, campgrounds, caravans, condos, luxury tents, agritourism, lodges, boats, hotels, recreational vehicles and chalets.

  • What are some of the most-loved vacation rentals available in Maryland?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Econo Lodge Frederick I-70.

  • Are there any pet-friendly vacation rentals in Maryland?

    There are a number of dog and pet-friendly Maryland vacation rentals, with around 5% allowing you to bring your pet along with you.

Where to stay in Maryland?

Our map will help you find the perfect place to stay in Maryland by showing you the exact location of each vacation home.

Everything you need to know for your stay in Maryland

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