Vacation Homes in Maryland

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Top Cities in Maryland

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Washington

Washington
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Baltimore

Baltimore

Our top choices for Maryland vacation homes

Smart TV

Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage

Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage
Midtown Ocean City
8.6 out of 10, Excellent, (7 reviews)
Unit 2 South - New Flooring Stairs & Hallways 2026 4bed/3.5 bath/3 car garage
Living area

Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.

Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.
North Ocean City
Spacious 4-bedroom house on the water in Caine Keys II, Ocean City, MD.
Outdoor dining

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic District
10.0 out of 10, Exceptional, (246 reviews)
"Perfect location and lovely place for a weekend getaway!"
United States
Krista L.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.8 out of 10, Exceptional, (201 reviews)
"This was an amazing experience to stay in a house that was here during the battle, look forward to may more visits while I see the place I love. "
United States
Dave W.
The price is AED 533
AED 642 total
includes taxes & fees
14 Jun - 15 Jun
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Dining

Beautiful Federal Hill home!

Beautiful Federal Hill home!
Federal Hill
9.4 out of 10, Exceptional, (54 reviews)
"Great location and neighborhood, and easy to get to our event at the Convention Center"
United States
Joel S.
Beautiful Federal Hill home!
Property grounds

Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.4 out of 10, Very Good, (54 reviews)
"Perfect place for our group in BMore for a literary conference. Location and amenities were exactly what we needed. Host was responsive and easy to work with. Great place! Thanks!"
United States
Michael C.
The price is AED 379
AED 1,061 total
includes taxes & fees
14 Jun - 15 Jun
Rooftop Deck Escape! Free Parking!
Living area

DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79

DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79
Silver Spring
9.2 out of 10, Wonderful, (18 reviews)
"Great place to stay. Very convenient to everything in the city."
United States
Stephen R.
The price is AED 238
AED 792 total
includes taxes & fees
14 Jun - 15 Jun
DE LUXE KING-SIZE BED Master Bedroom + 2 SLEEPING SOFAS in LR - WHOLE SUITE 79
Dining

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, (69 reviews)
"The place was clean and the communication was excellent. We would stay there again."
United States
Walter C.
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Smart TV

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, (113 reviews)
"Clean home , great location. Perfect for couple "
United States
Austin G.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Private kitchen

Renovated Farmhouse located near the C and O Canal

Renovated Farmhouse located near the C and O Canal
Hancock
9.6 out of 10, Exceptional, (24 reviews)
"The house was spacious, clean and well decorated. We enjoyed the older house ambiance with modern amenities at a reasonable price. "
United States
Kevin C.
The price is AED 661
AED 954 total
includes taxes & fees
14 Jun - 15 Jun
Renovated Farmhouse located near the C and O Canal
Smart TV, fireplace

Private Pool & Stunning Bay Views on Kent Island

Private Pool & Stunning Bay Views on Kent Island
Stevensville
9.2 out of 10, Wonderful, (28 reviews)
"Great time at a nice place and location."
United States
Michael S.
Private Pool & Stunning Bay Views on Kent Island
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is AED 992
AED 2,190 total
includes taxes & fees
15 Jun - 16 Jun
Charming Annapolis WaterVIEW Home
Exterior detail

Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (6 reviews)
Grace Cottage, St Michaels Walk to everything!
Fridge, microwave, oven, stovetop

Affordable Luxury Town Home in Federal Hill Baltimore.

Affordable Luxury Town Home in Federal Hill Baltimore.
Riverside
9.4 out of 10, Exceptional, (80 reviews)
"Well stocked kitchen, clean bathroom, really conveniently located. "
United States
Shelby G.
Affordable Luxury Town Home in Federal Hill Baltimore.
Property grounds

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, (36 reviews)
"House was very clean and comfortable, and very convenient to downtown Cumberland. "
United States
Larry M.
The price is AED 441
AED 705 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Exterior

3-bedroom Townhome in Exciting Corner of Fells Point!

3-bedroom Townhome in Exciting Corner of Fells Point!
Fells Point
3-bedroom Townhome in Exciting Corner of Fells Point!
Indoor pool, a heated pool

VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20

VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20
Friendsville
10.0 out of 10, Exceptional, (23 reviews)
"Super responsive host and amazing property with ALL the amenities! The pool is incredible! We had a blast!"
United States
Todd C.
VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20
Smart TV, fireplace, video games, books

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side
9.8 out of 10, Exceptional, (32 reviews)
"This is a great home base for exploring the Chesapeake Bay Area. In all the rentals we’ve ever stayed at, this one was the most generous in stocking supplies for us to use and they were also the most welcoming to our dog. We’d love to visit again during warmer weather so we can enjoy that beautiful backyard. "
United States
Lauren W.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Interior

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
Stevensville
9.8 out of 10, Exceptional, (20 reviews)
"Wonderful location, very well maintained and appointed. "
United States
Katrina D.
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
Microwave, oven, stovetop, dishwasher

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

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (9 reviews)
"Host was wonderful! Enjoyed our weekend in a very clean, comfortable and peaceful place. Look forward to returning in warmer weather."
United States
Katherine P.
The price is AED 314
AED 852 total
includes taxes & fees
14 Jun - 15 Jun
Cute, Cozy 2-bedroom house in near Annapolis with water access
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

Harborside Hotel

Harborside Hotel

10/10 Excellent
"Free shuttle to a couple of nearby attractions and free breakfast."
Enrique 4-night trip
Posted less than an hour ago
Harborside Hotel