Holiday Homes in Western Maryland

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Holiday Homes in Western Maryland and around

Couples Retreat: The HayLoft- Rustic Escape For 2
WiFi, bed sheets

Couples Retreat: The HayLoft- Rustic Escape For 2

10.0 out of 10, Exceptional, (5)
"Peggy was wonderful and the hayloft was great! "
The price is €187
includes taxes & fees
6 Oct - 7 Oct
Couples Retreat: The HayLoft- Rustic Escape For 2
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

10.0 out of 10, Exceptional, (4)
"Very nice place .Quiet and peaceful"
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Primitive Cozy off grid tiny home with Starlink
Outdoor dining

Primitive Cozy off grid tiny home with Starlink

9.8 out of 10, Exceptional, (9)
"Awesome spot. Highly recommend. "
The price is €162
includes taxes & fees
5 Oct - 6 Oct
Primitive Cozy off grid tiny home with Starlink
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Terrace/patio

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (38)
"Very cute house! Fire pit area was very private. Hot tub is a bit in the open but has the curtains to make it feel more private. The house had everything we needed for our stay. "
The price is €224
includes taxes & fees
4 Nov - 5 Nov
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (24)
"Great, cozy little place. Nice little get-away. Host communicated well and was not overbearing. We enjoyed ourselves. "
The price is €156
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Oldtown Guesthouse
Fridge, microwave, oven, stovetop

Oldtown Guesthouse

10.0 out of 10, Exceptional, (23)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
The price is €158
includes taxes & fees
22 Oct - 23 Oct
Oldtown Guesthouse
The Lodge at Wisp-1 BDRM Luxury Sleeps 4
Pillow-top beds, iron/ironing board, WiFi, bed sheets

The Lodge at Wisp-1 BDRM Luxury Sleeps 4

9.0 out of 10, Wonderful, (2)
"We enjoyed our stay at Wisp Resort. We went for the fireworks which were awesome. They had free concerts 2 nights we were there which we really enjoyed."
The price is €317
includes taxes & fees
3 Nov - 4 Nov
The Lodge at Wisp-1 BDRM Luxury Sleeps 4
Spring Sale! Near Wisp! Hot tub & Fire pit! Walk to the lake! Great Location!
Outdoor spa tub

Spring Sale! Near Wisp! Hot tub & Fire pit! Walk to the lake! Great Location!

10.0 out of 10, Exceptional, (18)
"Our family had a great stay at Denise and Greg’s property. We will be back!"
The price is €437
includes taxes & fees
8 Oct - 9 Oct
Spring Sale! Near Wisp! Hot tub & Fire pit! Walk to the lake! Great Location!
Full home near C&O! Perfect for bikers or families!
Fridge, microwave, oven, stovetop

Full home near C&O! Perfect for bikers or families!

9.6 out of 10, Exceptional, (15)
"Super clean. Love the neighborhood and older houses. "
The price is €199
includes taxes & fees
15 Oct - 16 Oct
Full home near C&O! Perfect for bikers or families!
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terrace/patio

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

10.0 out of 10, Exceptional, (133)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is €302
includes taxes & fees
4 Nov - 5 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

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

9.8 out of 10, Exceptional, (188)
"Wonderful location near Antietam NP, Shepardstown, and Hagerstown. Small home but plenty of room. My family enjoyed their stay"
The price is €147
includes taxes & fees
31 Oct - 1 Nov
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Little cute house close to C&O canal
Property grounds

Little cute house close to C&O canal

8.8 out of 10, Excellent, (12)
"I loved the outside and on the inside it was so beautiful more then i expected. Its was a gteat way to celebrate my 9th year anniversary. Thank you would definitely go back."
The price is €135
includes taxes & fees
2 Nov - 3 Nov
Little cute house close to C&O canal
Renovated Farmhouse located near the C and O Canal
Exterior

Renovated Farmhouse located near the C and O Canal

9.2 out of 10, Wonderful, (16)
"It was very relaxing and comfortable to stay. "
The price is €225
includes taxes & fees
6 Oct - 7 Oct
Renovated Farmhouse located near the C and O Canal
Cabin: Wraparound Deck, WiFi, Grill, Dog-Friendly!
Outdoor dining

Cabin: Wraparound Deck, WiFi, Grill, Dog-Friendly!

10.0 out of 10, Exceptional, (2)
"The house was exactly as it looked in the pictures. It was stocked with everything we needed and was very clean. Very quiet location and easy to get to. "
The price is €286
includes taxes & fees
6 Oct - 7 Oct
Cabin: Wraparound Deck, WiFi, Grill, Dog-Friendly!
Modern, family-friendly, nature packed getaway
Property grounds

Modern, family-friendly, nature packed getaway

9.0 out of 10, Wonderful, (18)
"we lived three nights and enjoyed the family retreat. "
The price is €236
includes taxes & fees
5 Oct - 6 Oct
Modern, family-friendly, nature packed getaway
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Exterior detail

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

The price is €86
includes taxes & fees
6 Oct - 7 Oct
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (53)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
The price is €319
includes taxes & fees
4 Nov - 5 Nov
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
Outdoor dining

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

8.6 out of 10, Excellent, (10)
"Great location, everything was great and we would stay again!"
The price is €299
includes taxes & fees
4 Nov - 5 Nov
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Fridge, microwave, oven, stovetop

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (106)
"Great little farm house in a quaint little town "
The price is €259
includes taxes & fees
9 Oct - 10 Oct
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

9.4 out of 10, Exceptional, (115)
"Clean and comfortable, quiet and perfectly located, this the perfect place for enjoying downtown "
The price is €256
includes taxes & fees
6 Oct - 7 Oct
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"Very clean room and restroom. Excellent breakfast food and facilities. Comfortable bed and quiet air conditioner."
Jimmy 2-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

Find out more about Western Maryland

Find out more about Western Maryland

Western Maryland Holiday Homes information

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