Western Maryland Holiday Rentals

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Holiday Rentals in Western Maryland

Smart TV, fireplace, DVD player, books
Secluded, romantic cabin with hot tub on 12 acres of woodland.
10.0 out of 10, Exceptional, (55)
"We greatly enjoyed r stay at this little cottage & would definitely recommend! My husband & I both love the outdoors & took the opportunity to do some hiking at Rocky Gap State Park close by, which had some great trails & beautiful scenery!"
The price is NZ$547
includes taxes & fees
28 May - 29 May
Secluded, romantic cabin with hot tub on 12 acres of woodland.
Aerial view
Cozy, family-friendly, lakeview condo with gas grill & firepit
7.6 out of 10, Good, (30)
"Cute for 2 people, but if you have trouble with steps look for a different location. Bed in main bedroom was VERY tall off the ground and hard to get into for a 5 foot tall woman. Clean property, but although sleeps 6 is stated in rental, it was comfortable for myself and my friend on our girls weekend. Give local restaurant Black Bear Tavern a 5 star rating also. EXCELLENT service, selection, food was amazing and entertainment was spot on for what we were looking for. Location nearby...
Cozy, family-friendly, lakeview condo with gas grill & firepit
Property grounds
Deep Creek Lakefront Cabin, OWLS NEST, Kayaks, Hot Tub, Paddleboards,CLEAN,Cozy
10.0 out of 10, Exceptional, (280)
"Very cozy location. My wife and I stayed for our anniversary and enjoyed our stay. The hot tub was amazing and very clean. It was the perfect place for us and we would definitely recommend it. The only thing I would change would be to have a larger shower but it served its purpose. Great place with plenty of activities for all ages."
Deep Creek Lakefront Cabin, OWLS NEST, Kayaks, Hot Tub, Paddleboards,CLEAN,Cozy
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Property grounds
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
8.8 out of 10, Excellent, (65)
"Family and dogs enjoyed stay in this well-equipped cabin with a beautifiul working wood fireplace."
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.6 out of 10, Exceptional, (8)
"Beautiful property, quiet, and very spacious. This property had everything we were looking for in a getaway. My family enjoyed our time together here. We did have a power outage and I let Tony know as soon as the power went out. He was quick to respond and even gave updates. Loved the communication from Tony throughout our whole experience. Definitely would stay here again and at another one of his properties."
The price is NZ$477
includes taxes & fees
29 May - 30 May
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (61)
"Beautiful views from the wrap around porch. Comfortable inside including the bed. Lots of neat things to look at. Highly recommend!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (100)
"Perfect location in historic Middletown. Our daughter stayed over night to be our driver to graduations. She recommends a circulating fan for the basement bedroom! Apparently, we, at the age of 83, kept the house a little too warm!"
The price is NZ$502
includes taxes & fees
2 Jun - 3 Jun
Charming "Cream of the Crop" Cape ~❤️of Middletown
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is NZ$236
includes taxes & fees
9 Jun - 10 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Fridge, microwave, oven, stovetop
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
9.8 out of 10, Exceptional, (32)
"A diamond in such a remote area, the host has really gone above and beyond to make a relaxing and accommodating stay."
The price is NZ$518
includes taxes & fees
17 Jun - 18 Jun
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
Exterior
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
10.0 out of 10, Exceptional, (400)
"The Nirvana cabin is in a wonderfully quiet little subdivision that is easy access to restaurants and parks. Clean and just a delight to visit."
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Property grounds
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
8.8 out of 10, Excellent, (28)
"The place is pretty nice. Just perfect for us. Other than some very minor issues such as dated appliances, the place was very well maintained. We really enjoyed our stay. The host is always there to answer our questions. Definitely a great place to stay."
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (50)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
Fridge, microwave, stovetop, dishwasher
Deep Creek Lake Townhome w/Deck & Water Views
9.4 out of 10, Exceptional, (24)
"Amazing views, great area."
Deep Creek Lake Townhome w/Deck & Water Views
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is NZ$362
includes taxes & fees
2 Jun - 3 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Interior
Little cute house close to C&O canal
10.0 out of 10, Exceptional, (2)
"I felt very cozy and comfortable in this small home, at the top of the hill (great views). Everything was arranged just right. Communication with the host was very easy. I would happily return. Beth"
The price is NZ$277
includes taxes & fees
28 May - 29 May
Little cute house close to C&O canal
Interior
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, (17)
"We had previously visited Frederick last November and had only been able to spend a little bit of our visit in Historic Frederick. We loved staying in historic Frederick and the property was unique, very clean and well laid out. I should have realized was that 'penthouse' in a historic home would mean steps. I am blind in one eye and have poor physical balance so carrying luggage up stairs is challenging. Nonetheless, we loved the layout and amenities of the property. The view from the deck was...
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Property grounds
*Daley's Doll House At Antietam*
9.8 out of 10, Exceptional, (87)
"My dog and I enjoyed the serenity and comfort of this adorable house."
*Daley's Doll House At Antietam*
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Fridge, microwave, oven, stovetop
Lakefront, dog friendly, dock slip, hot tub, and fire pit
10.0 out of 10, Exceptional, (14)
"We all really enjoyed our stay. The hosts were quick to reply. The house was beautiful and clean!"
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Interior detail
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
9.8 out of 10, Exceptional, (207)
"Had a great time at this property and were able to take advantage of the screened in porch and fireplace. Neighborhood was very nice and checkin was easy. They were very accommodating for the three dogs that also visited the property with us."
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Don't see what you're looking for?
See all available properties in Western Maryland
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.

Other types of properties in Western Maryland you may be interested in

Street view
Rocky Gap Casino & Resort
3.0 star property
8.8 out of 10, Excellent, (1008)
"It is a beautiful resort, but the bathrooms need attention in the rooms and in the casino."
The price is NZ$234
includes taxes & fees
28 May - 29 May
Rocky Gap Casino & Resort
Room, 2 Queen Beds, Non Smoking
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1010)
"Nice and clean. Very good quality-price ratio."
The price is NZ$147
includes taxes & fees
16 Jun - 17 Jun
Country Inn & Suites by Radisson, Frederick, MD
Exterior
Hilton Garden Inn Frederick
3.0 star property
9.0 out of 10, Wonderful, (1007)
"The check-in service was excellent! unfortunately, there was a problem. The hotel had a main water pipe burst at 3:45am. that resulted in the entire hotel being evacuated. I do want to say the check-in clerk was exceptional in handling this situation. He assured us the hotel would give us a refund if we called Expedia. I was given the info. that Expedia needed to process the refund and it appears that this will be taken care of. Thank-you so much and thank-you (check-in clerk) Art."
The price is NZ$183
includes taxes & fees
9 Jun - 10 Jun
Hilton Garden Inn Frederick
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Western Maryland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Western Maryland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Western Maryland. Seeing all the best attractions is bound to make you fall in love with Western Maryland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Western Maryland short-term rentals, that won’t be hard to do.

Recent reviews of Western Maryland properties
Expedia verified reviews

Days Inn by Wyndham Westminster

Days Inn by Wyndham Westminster

5/5 Excellent
"Not the Hilton but reliable. Have stayed there a few times. Clean"
A verified traveller stayed at Days Inn by Wyndham Westminster
Posted 1 day ago
Days Inn by Wyndham Westminster