Maryland holiday rentals

Search hundreds of travel sites at once for holiday home deals in Maryland

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Maryland holiday rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$28 - $638$638 - $1,247$1,247 - $1,857$1,857 - $2,466$2,466+ per night

Property type

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Maryland

Show all
Charity's Haven II - Waldorf
Charity's Haven II
Waldorf, MD, United States
7.9Good(69)
Homestay
Parking
$110+
Check availability
The Haven at Charity House - Waldorf
The Haven at Charity House
Waldorf, MD, United States
7.5Good(94)
Homestay
Parking
Free Wi-Fi
$115+
Check availability
The Oasis - Clinton
The Oasis
Clinton, MD, United States
8.6Very Good(43)
Homestay
Parking
Free Wi-Fi
$126+
Check availability
Nock Apartments - Ocean City - Balcony
Nock Apartments
Ocean City, MD, United States
7.9Good(598)
Apartment
Parking
Free Wi-Fi
Pet friendly
$181+
Check availability
Shore Point Cottages - Ocean City - Pool
Shore Point Cottages
Ocean City, MD, United States
9.1Wonderful(303)
Cottage
Parking
Free Wi-Fi
Pool
Pet friendly
$241+
Check availability
Extraordinary Oceanfront Penthouse - Unit 1210 - Ocean City
Extraordinary Oceanfront Penthouse - Unit 1210
Ocean City, MD, United States
House
Parking
Free Wi-Fi
Pool
$427+
Check availability
Luxe Oceanfront Escape Private Balcony & Wet Bar - Ocean City - Living room
Luxe Oceanfront Escape Private Balcony & Wet Bar
Ocean City, MD, United States
10Wonderful(13)
Condo
Parking
Free Wi-Fi
Pool
$432+
Check availability
Extraordinary Oceanfront Escape - Unit 1109 - Ocean City
Extraordinary Oceanfront Escape - Unit 1109
Ocean City, MD, United States
6.0Okay(1)
House
Parking
Free Wi-Fi
Pool
$433+
Check availability
Extraordinary Oceanfront Penthouse - Unit 1209 - Ocean City
Extraordinary Oceanfront Penthouse - Unit 1209
Ocean City, MD, United States
House
Parking
Free Wi-Fi
Pool
$434+
Check availability
Spectacular Oceanfront Escape - Unit 704 - Ocean City - Living room
Spectacular Oceanfront Escape - Unit 704
Ocean City, MD, United States
Condo
Parking
Free Wi-Fi
Pool
$445+
Check availability
Extraordinary Oceanfront Escape - Unit 809 - Ocean City
Extraordinary Oceanfront Escape - Unit 809
Ocean City, MD, United States
House
Parking
Free Wi-Fi
Pool
$445+
Check availability
Cozy Suburban Haven!!! - Waldorf - Bedroom
Cozy Suburban Haven!!!
Waldorf, MD, United States
5.0Fair(1)
House
Parking
Free Wi-Fi
$537+
Check availability
Marigot Beach 209 condo - Ocean City
Marigot Beach 209 condo
Ocean City, MD, United States
5.0Fair(3)
Apartment
Parking
Free Wi-Fi
Pool
$549+
Check availability
Extraordinary Oceanfront Penthouse - Unit 1211 - Ocean City - Living room
Extraordinary Oceanfront Penthouse - Unit 1211
Ocean City, MD, United States
10Wonderful(3)
House
Parking
Free Wi-Fi
Pool
$558+
Check availability
Spacious 5-Bedroom House With In Ground Pool - Fitness Room, Poker Room & Arcade - Waldorf - Kitchen
Spacious 5-Bedroom House With In Ground Pool - Fitness Room, Poker Room & Arcade
Waldorf, MD, United States
10Wonderful(1)
House
$1,470+
Check availability
Charming 4-bedroom house with WiFi, fitness room in superb Waldorf - Waldorf - Building
Charming 4-bedroom house with WiFi, fitness room in superb Waldorf
Waldorf, MD, United States
House
$2,904+
Check availability
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 81 days before your stay begins to get the best price for your Maryland vacation rental.
Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
May
$377
$333
Cheapest month to stay with an average 57% drop in price.
Most expensive month to stay with an average 30% 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 holiday rental

  • If you’re looking for a cheap holiday rental in Maryland, you should consider visiting during the low season. The cheapest holiday homes in Maryland can be found in August and July.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Maryland for 9 days.
  • Pool, pet friendly, hot tub, and beachfront are the most popular holiday rental property amenities in Maryland
  • Holiday rentals in Maryland are around 19% more expensive than hotels on average. Search here to compare prices for all accommodation types in Maryland.

FAQs when booking a holiday home in Maryland

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

    Based on KAYAK holiday rental searches, the most popular destination is Suitland (25% of total searches to Maryland). The next most popular destinations are Olney (25%) and Rockville (25%). Searches for holiday rentals in Frederick (25%) are also popular.

  • 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 $108. 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 $103 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 houses, homestays, apartments, cottages, bungalows, cabins, campgrounds, caravans, condos, luxury tents, villas, agritourism, lodges, hotels and houseboats.

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

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

  • 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.

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 holiday home.

Everything you need to know for your stay in Maryland

Complete your trip to Maryland

Flights to Maryland
Car rentals in Maryland