Holiday Homes in Maryland

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Maryland Accommodation: Most Popular Cities to Stay

Annapolis
Holiday HomesHoliday Homes

Annapolis

Annapolis

Featured Holiday Homes in Maryland

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is £1,138
per night
8 May - 9 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Caribbean Oasis with Pool Home - 25 mins to USNA!
Interior
Caribbean Oasis with Pool Home - 25 mins to USNA!
10.0 out of 10, Exceptional, (1)
"The house was exactly as promised! We were very happy with the accommodations!"
The price is £467
per night
6 May - 7 May
Caribbean Oasis with Pool Home - 25 mins to USNA!
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
Beach
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
10.0 out of 10, Exceptional, (69)
"Perfect for relaxation, with stunning lake views and cozy amenities. Ideal for a peaceful getaway."
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
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Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly
Beach
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly
10.0 out of 10, Exceptional, (3)
"Easier walk to the beach than anticipated. Great location and a very cute and live-able space. We felt very at home with our two boys."
Inviting home near beaches with fast WiFi, AC, full kitchen & W/D - dog-friendly
Sun, Sand, Beach & Boardwalk
Property grounds
Sun, Sand, Beach & Boardwalk
10.0 out of 10, Exceptional, (7)
"We had a wonderful week at Shelly’s place in Ocean City. The house was so welcoming when we arrived with soft music playing on the tv, lights on and a bottle of wine waiting for us. The view from the porch and upper deck are awesome! Lots of thoughtful touches like hand soap, wipes, shampoo etc. were provided. Our friend joined us for 2 nights and she loved sitting on the porch watching the world go by on the boardwalk too. We hope to come back next year."
Sun, Sand, Beach & Boardwalk
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown
Fridge, microwave, oven, stovetop
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown
10.0 out of 10, Exceptional, (14)
"The space was perfect and very clean. The plug-ins were a little intense for me and gave me a headache. Once I unplugged them and aired out the space, I was fine."
Modern Oasis - Close to M&T Stadium, John Hopkins & Downtown
Waterfront Jolly Roger with Private Pier mins to Annapolis
Property grounds
Waterfront Jolly Roger with Private Pier mins to Annapolis
10.0 out of 10, Exceptional, (25)
"Beautiful views, quiet location. Enjoyed watching the birds with our dog. Primary bedroom - comfortable large bed and very nice bathroom. Our son loved playing ping pong and foosball downstairs."
Waterfront Jolly Roger with Private Pier mins to Annapolis
3Bd House Walk to DC Metro
Fridge, microwave, oven, stovetop
3Bd House Walk to DC Metro
10.0 out of 10, Exceptional, (43)
"We stayed here to visit the Mall and it was exactly as described. The walk to the Metro is a little longer then we'd hoped (took about an hour to get down on the Mall from our house), but the neighborhood is lovely and the grocery store on the way to and from the Metro was super handy. We'd stay again!"
3Bd House Walk to DC Metro
* Lovely Gem w/ Perfect Combo of Flair & Class *
Fridge, microwave, oven, stovetop
* Lovely Gem w/ Perfect Combo of Flair & Class *
10.0 out of 10, Exceptional, (36)
"It was my daughters senior game for Towson lacrosse !!! Easy huber !!! A little noise from main st … to be expected ‼️"
The price is £219
per night
13 May - 14 May
* Lovely Gem w/ Perfect Combo of Flair & Class *
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Very Spacious 3 level Bay Front vacation house
Property grounds
Very Spacious 3 level Bay Front vacation house
10.0 out of 10, Exceptional, (21)
"Loved the house, so much fun for my extended family for Easter. Beautiful views, awesome game room."
Very Spacious 3 level Bay Front vacation house
Waterfront Getaway-walk to beach and local favorites!
Property grounds
Waterfront Getaway-walk to beach and local favorites!
10.0 out of 10, Exceptional, (19)
"Everything about our stay was perfect. Communication with Paula, check-in, cleanliness, comfort of furniture was all top notch. We will stay again the next time we are in the area!"
Waterfront Getaway-walk to beach and local favorites!
Water front, open bay views from both decks!!
View from property
Water front, open bay views from both decks!!
10.0 out of 10, Exceptional, (21)
"This place was beautiful.I would recommend this place and the host was very attentive"
Water front, open bay views from both decks!!
3 Bedroom Pet Friendly Single Family Home
Fridge, microwave, coffee/tea maker, toaster
3 Bedroom Pet Friendly Single Family Home
10.0 out of 10, Exceptional, (1)
"This house has a cute beachy bungalow vibe. Nice neighborhood and a short walk to the oceanfront in one direction and to the bay in the other. Very clean and well kept property."
3 Bedroom Pet Friendly Single Family Home
Peaceful & Secluded Knoxville Retreat w/ Deck
Property grounds
Peaceful & Secluded Knoxville Retreat w/ Deck
10.0 out of 10, Exceptional, (25)
"Beautiful little house up in the mountains. The house has everything that you would ever need. Plenty of games for inside and out. Owners were very responsive. Great getaway!"
Peaceful & Secluded Knoxville Retreat w/ Deck
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (62)
"I’ve reviewed this home several times, still 5/5"
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Beach view condo with private deck
Fridge, microwave, oven, stovetop
Beach view condo with private deck
9.8 out of 10, Exceptional, (7)
"Great location with partial ocean view, just right for a weekend beach trip!"
Beach view condo with private deck
Central Lake House with Private Dock! Walk to Area Hot Spots!
Property grounds
Central Lake House with Private Dock! Walk to Area Hot Spots!
9.8 out of 10, Exceptional, (18)
"I recently stayed on property and it was a lovely time. You can't ask for a better location if you want to be close to the nightlife of the area. Only issue was a broken piece of the basement stairway, but I wouldn't hold that against the houses rating as it was only a minor flaw."
Central Lake House with Private Dock! Walk to Area Hot Spots!
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Exterior
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
9.8 out of 10, Exceptional, (71)
"Comfortable relaxing atmosphere in soothing colors. The owners have thought of almost everything to complete your vacation needs. We really appreciate the quality materials provided."
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
FletchersCove-DeepCreekLake-PrivateDock-HotTub
Marina
FletchersCove-DeepCreekLake-PrivateDock-HotTub
9.8 out of 10, Exceptional, (25)
"We loved the home and lake views, not much to do off-season. Host’s communications were thorough. Check in and check out was seamless. Would recommend."
FletchersCove-DeepCreekLake-PrivateDock-HotTub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Maryland Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in Maryland?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in Maryland?

Choose from 4137 beautiful holiday homes in Maryland for your getaway.


How much is a holiday home in Maryland?

You can find perfect holiday homes in Maryland for as low as £219 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Maryland?

Find the best deals on Maryland holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Maryland?

There’s no better way to spend your well-earned holiday than in a private, cosy Maryland holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Maryland.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Maryland holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Maryland—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Maryland car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Maryland Holiday Homes information

Number of reviews
587
Accommodation
4137 Holiday Homes
Lowest Price
£219
Highest Price
£1,138

Maryland Hotel Reviews
Expedia verified reviews

Hyatt Place National Harbor

Hyatt Place National Harbor

5/5 Excellent
"Beautiful views of the river and a very helpful staff made it a wonderful weekend getaway. "
A verified traveller stayed at Hyatt Place National Harbor
Posted 15 hours ago
Hyatt Place National Harbor

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