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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 79 Cottages in Middletown with updated reviews, rates, and availability.

The Carriage House at Carrot Top Cottage
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (35)
"My girlfriend and I will definitely be coming back to this spot when we visit Harpers Ferry again. Frederick MD is also just 20 mins away for more food options. "
The price is AED 386
AED 655 total
includes taxes & fees
15 Apr - 16 Apr
The Carriage House at Carrot Top Cottage
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (35)
"The house is adorable inside and out! Pulling up to the house you just know that you are in for a treat! The decor is absolutely perfect. The home is very comfortable and has all that you need for a exceptional stay...and then some. Walking the streets and admiring the beautiful old homes is so relaxing! This Is Our New " Happy Place!""
Carrot Top Cottage surrounded by National Park
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

10.0 out of 10, Exceptional, (1)
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (35)
"The house is very well preserved classical duplex home on a road with plenty of parking with easy walking access to Market street just a couple blocks away. Its ideal for our type of stay when we want to check out the city."
The price is AED 477
AED 989 total
includes taxes & fees
28 Apr - 29 Apr
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Bring Your Own Boat - Meticulously restored house on the Potomac River
Living area

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

10.0 out of 10, Exceptional, (3)
"Clean, everything you need is there. Peaceful."
The price is AED 275
AED 592 total
includes taxes & fees
15 Apr - 16 Apr
Bring Your Own Boat - Meticulously restored house on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Property grounds

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. "
The price is AED 650
AED 1,989 total
includes taxes & fees
28 Apr - 29 Apr
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

10.0 out of 10, Exceptional, (15)
"The view of this house is amazing! Absolutely beautiful!"
The price is AED 492
AED 1,572 total
includes taxes & fees
23 Apr - 24 Apr
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (25)
"The house was simply perfect for our stay. All you can ask for. Our daughter’s wedding was near by and wanted to explore downtown Leesburg as well. Everything was walkable and so many places to explore. Michael the host was amazing and hospitality 5 stars!!! We will definitely book again when in the area. "
The price is AED 775
AED 1,719 total
includes taxes & fees
14 Apr - 15 Apr
Royal Heritage Home @ Historic Leesburg
Lake View Retreat - Cottage Near a Peaceful Lake!
Property grounds

Lake View Retreat - Cottage Near a Peaceful Lake!

9.6 out of 10, Exceptional, (17)
"Beautiful location to relax and enjoy friends. This house was huge. Plenty of room for the 3 of us...could have been 8, lol. "
The price is AED 419
AED 1,392 total
includes taxes & fees
24 Apr - 25 Apr
Lake View Retreat - Cottage Near a Peaceful Lake!
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"What a lovely, cozy, clean property! The location was in the heart of Harper’s Ferry. Everything advertised was exactly as described, even nicer, inside and out! Cathy, our property manager was communicative and helpful. We will be back!!"
The price is AED 680
AED 1,195 total
includes taxes & fees
17 Apr - 18 Apr
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Cottage at Gray Fox- Many Attraction- Pet Friendly
Fridge, microwave, oven, stovetop

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Wonderful property for a girls' getaway! The owners are very responsive to messages and communicated well with us. Clean, comfy beds, had everything we needed. The hot tub was a plus on a snowy weekend."
Cottage at Gray Fox- Many Attraction- Pet Friendly
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (20)
"This property was everything we hoped for in a weekend getaway home! So clean, beautifully decorated, and decked out with everything we wanted and more. We will definitely be booking with Mountain Mama again. "
The price is AED 474
AED 1,395 total
includes taxes & fees
24 Apr - 25 Apr
Woodsy Retreat with a Hot Tub and Seasonal Views!
Laurel Cottage in the heart of Harpers Ferry
Fridge, microwave, oven, stovetop

Laurel Cottage in the heart of Harpers Ferry

Laurel Cottage in the heart of Harpers Ferry
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Exterior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

10.0 out of 10, Exceptional, (1)
"We had a a great experience at this cabin getaway. The property was immaculate, cozy and well-equipped. The host was incredibly responsive and thoughtful. We can't wait to come back!"
The price is AED 918
AED 1,558 total
includes taxes & fees
13 Apr - 14 Apr
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Firehouse Cottage | Walk to all of downtown HF
1 bedroom, iron/ironing board, travel crib, WiFi

Firehouse Cottage | Walk to all of downtown HF

The price is AED 533
AED 883 total
includes taxes & fees
14 Apr - 15 Apr
Firehouse Cottage | Walk to all of downtown HF
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (117)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Property grounds

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

10.0 out of 10, Exceptional, (137)
"It beautiful vacation place. The host is simply the best whatever you need she has your back.You will love the beauty of the place."
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Peaceful Lakefront Cottage with Mountain Views!
Fridge, microwave, oven, stovetop

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (24)
"Wintertime visit. Very peaceful. "
The price is AED 768
AED 1,897 total
includes taxes & fees
21 Apr - 22 Apr
Peaceful Lakefront Cottage with Mountain Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Smart TV

Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!

10.0 out of 10, Exceptional, (1)
"This treehouse was so dreamy and private! I hope we get to stay here again some time soon!"
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Terrace/patio

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

10.0 out of 10, Exceptional, (3)
"Cozy remodeled property. Plenty of space for 9 adults and teens to celebrate Christmas. George is a great host. Highly recommend. "
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
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
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (93)
"Traveled from Baltimore to get away for a few days. Great location and mountain views. Cozy vintage cabin nicely renovated. "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Fridge, microwave, oven, stovetop

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (90)
"Adorable log cabin stay. We enjoyed the quiet neighborhood and cute town with beautiful old homes! It was a nice 3 day respite "
The price is AED 294
AED 720 total
includes taxes & fees
16 Apr - 17 Apr
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields
Exterior

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very Good, (27)
"Our overall experience was nice and relaxing place to be. However, during the cold months. The second floor was warm enough to sleep, but the first floor was very cold, especially when it gets down to 19 at night when there’s no heat because all the heat travels to the second floor/loft. There was a space heater, but didn’t realize it until after we left. The host was easy to get a hold of through messages. The only recommendation I would say is maybe put a firebox insert in the fireplace to...
Serene Log Cabin Nestled Among the Battlefields
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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