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Western Maryland Holiday Rentals

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Our top choices for Western Maryland holiday rentals

1. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Great location, clean place. "
United States
Warren B.
The price is NZ$338
includes taxes & fees
8 Sept - 9 Sept
Cozy, dog-friendly, downtown

2. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (11 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
The price is NZ$381
includes taxes & fees
31 Aug - 1 Sept
Huge 1br apt, baby-friendly, dogs, walkable downtown

3. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is NZ$360
includes taxes & fees
7 Sept - 8 Sept
Pet-friendly, heart of downtown

4. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (101 reviews)
"Great place!"
United States
Danielle G.
The price is NZ$551
includes taxes & fees
18 Aug - 19 Aug
Modern Condo Right off Market Street

5. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (134 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveller
The price is NZ$487
includes taxes & fees
30 Aug - 31 Aug
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

6. Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is NZ$498
includes taxes & fees
22 Aug - 23 Aug
Charming "Cream of the Crop" Cape ~❤️of Middletown

7. Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (51 reviews)
"We had a wonderful Mother’s Day weekend visiting our daughter and her family! The home was exactly as pictured, very clean and a great location! We could easily walk to our daughter’s house and anything in downtown Frederick. Would definitely stay here agin! "
United States
Dawn W.
The price is NZ$457
includes taxes & fees
19 Aug - 20 Aug
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

8. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (82 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is NZ$239
includes taxes & fees
31 Aug - 1 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

9. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is NZ$579
includes taxes & fees
18 Aug - 19 Aug
Luxury Condo In Downtown Frederick

10. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is NZ$491
includes taxes & fees
31 Aug - 1 Sept
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

11. Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
The price is NZ$542
includes taxes & fees
7 Sept - 8 Sept
Chic, pets, walk to downtown

12. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is NZ$733
includes taxes & fees
18 Aug - 19 Aug
Rural & Historic Detour Escape w/ Horses On-site!

13. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (96 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is NZ$554
includes taxes & fees
20 Aug - 21 Aug
Antietam Creek - Quiet 2 Bedroom Cabin

14. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (22 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is NZ$372
includes taxes & fees
18 Aug - 19 Aug
Quaint Mini Cottage in Shepherdstown - Walking Distance

15. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (72 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is NZ$628
includes taxes & fees
24 Aug - 25 Aug
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

16. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (19 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is NZ$813
includes taxes & fees
25 Aug - 26 Aug
Newly constructed 6 bedroom home

17. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is NZ$617
includes taxes & fees
1 Sept - 2 Sept
Antietam Look Out - Incredible Sunset Views!

18. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (70 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is NZ$538
includes taxes & fees
24 Aug - 25 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

19. 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
9.6 out of 10, Exceptional, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is NZ$297
includes taxes & fees
22 Aug - 23 Aug
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

20. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"It’s the perfect river cabin to stay at. It’s older home so layout is awkward but it has been renovated and was nice and clean and perfect for our trip. Nice open dining/kitchen and living areas!! Host is AMAZING! She is so responsive and so helpful. We will definitely be back to stay!! "
United States
Amber W.
The price is NZ$319
includes taxes & fees
18 Aug - 19 Aug
Bring Your Own Boat - Meticulously restored house on the Potomac River
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 Western Maryland Hotel Reviews

Find out more about Western Maryland

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.