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Search Cottages in Middletown

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Compare 54 Cottages in Middletown with updated reviews, rates, and availability.

Lovettsville Cottage in Heart of Wine Country
10.0 out of 10, Exceptional, (28)
"Family reunion to get 3 sisters together. My Mother-in-Law is 90 and we drove to VA so she can visit with her 88 and 80 year old sisters. We did have an issue wtih the 2 statements below provided in an email on 9Sept2024, which is after the window for cancelation. The homeowner isn't just next door, they are adjoining, which isn't clear in the description. It is also not shown in the pictures. We expected quiet time for morning coffee outdoors, instead we were able to hear the homeowner on...
Lovettsville Cottage in Heart of Wine Country
The Carriage House at Carrot Top Cottage
9.8 out of 10, Exceptional, (28)
"My wife and I had a fantastic time. Very warm and cozy cottage. Walking distance to everything, but tucked away enough to enjoy your privacy. Would definitely stay with them again."
The price is SAR 368
SAR 635 total
includes taxes & fees
18 Nov - 19 Nov
The Carriage House at Carrot Top Cottage
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
2.0 star property
10.0 out of 10, Exceptional, (6)
"The property was perfect for our needs. Pet friendly, fenced in yard, and clean. The grill was perfect, new and well kept. That allowed an evening in enjoying the property and a great steak. The host couple was very attentive, friendly and helpful. We would stay anytime we were in the area and we both hope that will be soon. Thank you for a great visit. Lewis Family"
The price is SAR 620
SAR 1,141 total
includes taxes & fees
12 Nov - 13 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (113)
"Enjoyed sitting on the deck above the river in the evenings, quiet and peaceful looking forward to staying there again."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Lake View Retreat - Cottage Near a Peaceful Lake!
9.6 out of 10, Exceptional, (14)
"This property was a perfect place to stay for our group. While it was a little out of the way, it suited our needs, was clean, and very comfortable. The owners made quick communication with them easy. Definitely recommend!"
The price is SAR 413
SAR 1,329 total
includes taxes & fees
7 Nov - 8 Nov
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Lakefront Cottage with Mountain Views!
10.0 out of 10, Exceptional, (21)
"Really enjoyed stay home was great "
The price is SAR 841
SAR 2,017 total
includes taxes & fees
5 Dec - 6 Dec
Peaceful Lakefront Cottage with Mountain Views!
Bear Mountain Cottage
10.0 out of 10, Exceptional, (6)
"We were in town for a wedding, Bear Mountain Cottage felt like home! Everyone was super helpful to booking/recommendations of things to do! Bonus points for the cottage being super clean/updated and even better pet friendly! We hope to be back! "
Bear Mountain Cottage
Royal Heritage Home @ Historic Leesburg
9.8 out of 10, Exceptional, (23)
"Great location"
The price is SAR 890
SAR 1,905 total
includes taxes & fees
11 Nov - 12 Nov
Royal Heritage Home @ Historic Leesburg
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Modern Country Cottage in Wine Country
8.8 out of 10, Excellent, (3)
"Our family was in the area for a wedding and chose this property because it had 3 bedrooms and bathrooms. It was quiet and comfortable. Basement area seems like it is a work in progress."
Modern Country Cottage in Wine Country
Cozy Creek Retreat by Whitetail Resort W/ hot tub
10.0 out of 10, Exceptional, (1)
"This was an excellent place to stay. Incredibly clean, well kept, and stocked with many helpful home items. I will be looking to book again next time I am in the area."
Cozy Creek Retreat by Whitetail Resort W/ hot tub
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
10.0 out of 10, Exceptional, (16)
"Check in was seamless. The place was perfect for three couples with all the master suites. "
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Lock Keepers Cottage on C&O Canal/Potomac River
10.0 out of 10, Exceptional, (47)
"Peaceful, tranquil and so much to explore right outside the door. The front porch is the perfect location for meals and reading. I absolutely loved riding my bike on the C&O canal towpath. The cottage is beautiful and well decorated with lots of details. Can’t wait to come back! "
Lock Keepers Cottage on C&O Canal/Potomac River
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
10.0 out of 10, Exceptional, (2)
"This is a tremendous house. Clean, tons of towels, wash cloths, utensils.. Everything you could need to make it great is there. Just a tremendous job. The owner is fast and helpful with responses. Massive thanks! The inside open space is great!! We had all our group inside for meetings, and it worked awesome! The only things you need to be aware of: 1. You can not use the outside in it's current condition. There is broken glass and trash outside. (Looks like when they renovated...
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Cottage at Gray Fox- Many Attraction- Pet Friendly
10.0 out of 10, Exceptional, (20)
"Our family of four enjoyed the weekend away"
Cottage at Gray Fox- Many Attraction- Pet Friendly
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay and particularly enjoyed the location and sunny back deck! Ed was a kind and responsive host!"
The price is SAR 530
SAR 1,095 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Cottage w/ Hot Tub and 100-Mile Valley Views!
10.0 out of 10, Exceptional, (14)
"The view of this house is amazing! Absolutely beautiful!"
Cottage w/ Hot Tub and 100-Mile Valley Views!
Carrot Top Cottage surrounded by National Park
10.0 out of 10, Exceptional, (25)
"The house was very clean with a nice porch and backyard. It was about a 10 minute walk to lower Harpers Ferry and Bolivar. The house was perfect for our nice weekend tripto celebrate our 10 year anniversary. "
Carrot Top Cottage surrounded by National Park
Historic Schoolhouse on Winery Row
10.0 out of 10, Exceptional, (12)
"This VRBO home could not have been any better! It was clean, cozy, comfortable, and well stocked with everything you can possibly need. The owner, Lynn, answered all of our questions and responded to our text messages quickly. She could not have been more helpful. Location is ideal close to wineries and great restaurants. we enjoyed the grill on the back deck as well as the relaxing creek and chairs around the fire pit We enjoyed our stay here so much. We are looking forward to going back...
Historic Schoolhouse on Winery Row
Charming Home With Yard Near Shenandoah River!
3.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy house nestled in the mountains of West Virginia. Well-maintained, clean, great yard for pets and/or kids! Lovely grilling and fire pit area. We throughly enjoyed our stay!"
Charming Home With Yard Near Shenandoah 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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Other property types in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (84)
"Wow! What a beautiful cabin! Definitely would love to stay in this beautiful and peaceful home again! Thanks for sharing this awesome home with us! Margarita "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (86)
"Enjoyed our stay & the countryside location. This is the real deal for a log cabin historical property. "
The price is SAR 470
SAR 956 total
includes taxes & fees
10 Nov - 11 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (113)
"Lovely accommodations. Perfect for two couples. Clean and quiet. The town was charming and we enjoyed walking around and seeing the local scarecrow competition. "
The price is SAR 376
SAR 956 total
includes taxes & fees
10 Nov - 11 Nov
Charming "Cream of the Crop" Cape ~❤️of Middletown
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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