Maryland Holiday Rentals – KAYAK

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Best Maryland holiday rentals

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€14 - €1,070 €1,070 - €2,125 €2,125 - €3,180 €3,180 - €4,236 €4,236+ per night

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Free cancellation Free breakfast Free parking Free internet

Epic Brunswick Apartment with Deck! - Brunswick - Living room

Epic Brunswick Apartment with Deck!

Brunswick, MD, United States

9.1Wonderful(27)

Free Wi-Fi

Pet friendly

Air conditioning

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7 Mi to Baltimore Maryland Gem with Shared Yard! - Brooklyn Park - Building

7 Mi to Baltimore Maryland Gem with Shared Yard!

Brooklyn Park, MD, United States

Free Wi-Fi

Air conditioning

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Contemporary Hideaway Near Historic Harpers Ferry! - Knoxville - Living room

Contemporary Hideaway Near Historic Harpers Ferry!

Knoxville, MD, United States

9.0Wonderful(2)

Free Wi-Fi

Air conditioning

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Stunning sunsets Leonardtown apartment - Leonardtown - Living room

Stunning sunsets Leonardtown apartment

Leonardtown, MD, United States

Free Wi-Fi

Air conditioning

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Pet-friendly Community! | Near Parks | Woodmont Triangle | by GLS - Chevy Chase - Restaurant

Pet-friendly Community! | Near Parks | Woodmont Triangle | by GLS

Chevy Chase, MD, United States

8.0Very Good(1)

Air conditioning

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Downtown Harpers Ferry! Charming Historic House In Harpers Ferry National Park! - Harpers Ferry - Building

Downtown Harpers Ferry! Charming Historic House In Harpers Ferry National Park!

Harpers Ferry, WV, United States

9.8Wonderful(93)

Free Wi-Fi

Air conditioning

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Riverview Suite at La Soledad - Harpers Ferry - Living room

Riverview Suite at La Soledad

Harpers Ferry, WV, United States

9.7Wonderful(5)

Free Wi-Fi

Air conditioning

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Charming Brookland Retreat - Washington, D.C. - Living room

Charming Brookland Retreat

Brookland

Air conditioning

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Luxury Condo 2br close to Metro & NIH Walter Rees/Sightseeing/Museums/Zoo/shops - Chevy Chase - Kitchen

Luxury Condo 2br close to Metro & NIH Walter Rees/Sightseeing/Museums/Zoo/shops

Chevy Chase, MD, United States

9.5Wonderful(22)

Air conditioning

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Anne and Freds Leonardtown Home - Leonardtown - Living room

Anne and Freds Leonardtown Home

Leonardtown, MD, United States

9.3Wonderful(3)

Free Wi-Fi

Air conditioning

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Big Country Home - Harpers Ferry - Balcony

Big Country Home

Harpers Ferry, WV, United States

10Wonderful(10)

Free Wi-Fi

Air conditioning

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St. Michaels Waterfront Home - Easton - Living room

St. Michaels Waterfront Home

Easton, MD, United States

9.9Wonderful(28)

Free Wi-Fi

Air conditioning

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September Splender! Waterfront ,pool, Dock, Hot Tub.A Luxury Vip Vacation Rental - Royal Oak - Dining room

September Splender! Waterfront ,pool, Dock, Hot Tub.A Luxury Vip Vacation Rental

Royal Oak, MD, United States

9.5Wonderful(16)

Free Wi-Fi

Air conditioning

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Magnolia Cove - Royal Oak

Royal Oak, MD, United States

Parking

Free Wi-Fi

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Thorneton Point Estate - Easton - Pool

Thorneton Point Estate

Easton, MD, United States

9.7Wonderful(17)

Air conditioning

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25 Bedrooms - Retreat Center Waterfront Renovated - Royal Oak - Living room

25 Bedrooms - Retreat Center Waterfront Renovated

Royal Oak, MD, United States

Parking

Free Wi-Fi

Pool

Air conditioning

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Booking Insights

KAYAK’s insights for holiday 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 36 days before your stay begins to get the best price for your Maryland vacation rental.

Low season	High season	Average price (weeknight)	Average price (weekend night)
November	February	€186	€267
Cheapest month to stay with an average 29% drop in price.	Most expensive month to stay with an average 44% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Maryland for 3 days.
Pet-friendly, pool, hot tub, and beachfront are the most popular holiday rental property amenities in Maryland
Holiday rentals in Maryland are around 21% more expensive than hotels on average. Search here to compare prices for all accommodation types in Maryland.

What is the most popular holiday rental destination in Maryland?
Based on KAYAK holiday rental searches, the most popular destination is Hanover (50% of total searches to Maryland). The next most popular destinations are Baltimore (25%) and Fort Meade (25%).
How much is a holiday rental in Maryland for tonight?
In the last 72 hours, users have found Maryland holiday rentals for tonight for as little as €57. Search here for similar prices
How much is a holiday rental in Maryland for this weekend?
In the last 72 hours, users have found Maryland holiday rentals for this weekend for as little as €56 per night. Search here for similar prices
What types of holiday rentals are available in Maryland?
There are loads of different property types that you can make your holiday home in Maryland. You’ll find apartments, cottages, houses, houseboats, bungalows, cabins, campgrounds, caravans, condos, homestays, luxury tents, villas, agritourism, lodges, boats, hotels, motorhomes and chalets.
Are there any pet-friendly holiday rentals in Maryland?
There are a number of dog and pet-friendly Maryland holiday rentals, with around 3% allowing you to bring your pet along with you.

Everything you need to know for your stay in Maryland

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