A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

Holiday Homes in Maryland

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Top Cities in Maryland

A city skyline with high-rise buildings, a marina with boats, and a river.
Holiday HomesHoliday Homes

Baltimore

Baltimore

Our top choices for Maryland holiday homes

A deck with green chairs and a fire pit, surrounded by a house and trees.

1. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (31 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A beach with chairs and a pier in the background.

2. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is €464
includes taxes & fees
4 Oct - 5 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A dining area with a rectangular table surrounded by white chairs, a chandelier above, and a television on the wall.

3. 3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Silver Spring
10.0 out of 10, Exceptional, (88 reviews)
"Large and great location"
United States
JoAnn J.
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
A single-story brick house with a front porch, a garage, and a driveway.

4. Private Suite 3 near National Harbor Pvt Entry

Private Suite 3 near National Harbor Pvt Entry
Fort Washington
Private Suite 3 near National Harbor Pvt Entry
A rooftop terrace with a fire pit and seating area, overlooking a cityscape at night.

5. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, Excellent, (69 reviews)
"Great location loved the rooftop deck and had fun playing the shuffle board table."
United States
Heather M.
The price is €247
includes taxes & fees
5 Oct - 6 Oct
Rooftop Deck Escape! Free Parking!
A room with a fireplace, a mirror, a wreath, and a potted plant.

6. Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Historic District
9.4 out of 10, Exceptional, (22 reviews)
"Good location convenient to old town Annapolis and even can walk there"
United States
Thomas B.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
A waterfront restaurant with tables and an umbrella, a dock with a boat, and a sign indicating emergency exit only.

7. Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape

Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
Marley
9.2 out of 10, Wonderful, (7 reviews)
"Victor and Rose are fantastic hosts! We’ve booked with them multiple times and their property is just perfect for our group."
United States
MacKendrie P.
The price is €224
includes taxes & fees
1 Oct - 2 Oct
Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
A living room with a sofa, a wooden coffee table, a red chair, a white cabinet with glass doors, and a chandelier.

8. Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (70 reviews)
"Host was aces….place was great and right in the heart of town "
United States
Sean T.
Dollhouse in Central Historic St Michaels
A bathroom with a towel rack, a mirror, a sink, and a potted plant.

9. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.

Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Highfield-Cascade
10.0 out of 10, Exceptional, (6 reviews)
The price is €199
includes taxes & fees
26 Oct - 27 Oct
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
A spacious kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

10. Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (34 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is €297
includes taxes & fees
25 Oct - 26 Oct
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
A garden with a variety of flowers and plants, a wooden structure, and a white fence.

11. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (51 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is €172
includes taxes & fees
6 Oct - 7 Oct
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A house with beige siding, a white door, and a window with a white frame.

12. Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking

Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking
Silver Spring
9.4 out of 10, Exceptional, (6 reviews)
"Great spot. Great stay."
United States
Bernard
Cozy 1BR with Full Bath & Your Own Entrance, and convenient parking
A living room with a sofa, armchair, coffee table, dining table, chairs, and framed artwork on the wall.

13. Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Crofton
9.8 out of 10, Exceptional, (123 reviews)
"The townhome was perfect for our stay! It was clean and well equipped for our comfort. Close to shopping and restaurants and proximity to Baltimore and DC. If visiting my family that live in the area would hope to stay here again!"
United States
sandra c.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
A dining area with a table and chairs, three bay windows, and a vase with flowers.

14. Beautiful, Spacious Historic Victorian Near Ski Liberty

Beautiful, Spacious Historic Victorian Near Ski Liberty
Cascade
9.8 out of 10, Exceptional, (80 reviews)
"This is a beautiful home on a fantastic piece of land in rural northern Maryland. I highly recommend any group to stay here as a great mountain getaway."
United States
Max O.
Beautiful, Spacious Historic Victorian Near Ski Liberty
A modern kitchen with grey cabinets, a central island, and pendant lighting.

15. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is €308
includes taxes & fees
6 Oct - 7 Oct
Luxury Condo In Downtown Frederick
A wooden deck with outdoor furniture, a view of a lake, and a building with large windows.

16. In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Oakland
8.0 out of 10, Very good, (86 reviews)
"We would come again"
United States
Dennis & Naomi G.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
A hot tub with a view of a lake and a metal fence.

17. Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay
Perryville
9.2 out of 10, Wonderful, (65 reviews)
"Wonderful, relaxing place to stay. Hot tub is a fabulous addition!"
United States
Heidi L.
Sailor's Sunrise Cottage - Chesapeake Bay
A large house with a swimming pool, deck chairs, and a covered patio area.

18. Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge
9.6 out of 10, Exceptional, (98 reviews)
"The host, Virgina, was amazing, so accommodating. Beautiful property. Looking forward to hopefully booking next year. "
United States
Susan B.
Private 2 Acre Waterfront Family Retreat with Pool & Pier
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

19. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is €192
includes taxes & fees
12 Oct - 13 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A spacious living room with a sofa, a round coffee table, and a fireplace. There is a balcony with a view of the beach.

20. Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill

Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill
North Ocean City
8.8 out of 10, Excellent, (16 reviews)
"Liked the nearby beach and convenience"
United States
Arafat J.
Luxurious 6bd Semi-Private Pool Steps to Beach Bikes Grill
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.
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Top Maryland Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Parking You will have to use a garage or pay hotel $50.00 per night"
HAL 2-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Maryland

Maryland Holiday Homes information

Number of reviews
991
Accommodation
4843 Holiday Homes
Lowest Price
€172
Highest Price
€464

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