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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

The Carriage House at Carrot Top Cottage
Aerial view

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (36)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
The price is AED 386
AED 655 total
includes taxes & fees
6 May - 7 May
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)
"This cottage was like a home away from home! It was the perfect location and spotless. We would definitely stay again and recommend to anyone "
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)
"This was a good place to stay for two guys day hiking in the AT. It is clean, quiet, comfortable, and in a very good location. It had everything we needed."
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, (39)
"Great stay! "
The price is AED 514
AED 1,055 total
includes taxes & fees
6 May - 7 May
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Bring Your Own Boat - Meticulously restored house on the Potomac River
Game room

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 364
AED 691 total
includes taxes & fees
6 May - 7 May
Bring Your Own Boat - Meticulously restored house on the Potomac River
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Outdoor dining

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 481
AED 1,779 total
includes taxes & fees
14 May - 15 May
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, (16)
"We loved this place! It had everything we needed and everything was very comfortable. The sunset view from the hot tub was a highlight! We would stay here again."
The price is AED 367
AED 1,386 total
includes taxes & fees
5 May - 6 May
Cottage w/ Hot Tub and 100-Mile Valley Views!
Royal Heritage Home @ Historic Leesburg
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

9.6 out of 10, Exceptional, (27)
"Great location"
The price is AED 775
AED 1,690 total
includes taxes & fees
7 May - 8 May
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)
"Was really able to relax and enjoy during our brief stay. Would come again."
The price is AED 367
AED 1,305 total
includes taxes & fees
5 May - 6 May
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
10.0 out of 10, Exceptional, (11)
"We loved our stay. The location was central to everything we did; the car stayed in the driveway for almost our entire trip, and the yard is perfect for dogs. The house itself is exactly as shown in the pcs. Highly recommended "
The price is AED 680
AED 1,199 total
includes taxes & fees
4 May - 5 May
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Cottage at Gray Fox- Many Attraction- Pet Friendly
Aerial view

Cottage at Gray Fox- Many Attraction- Pet Friendly

10.0 out of 10, Exceptional, (21)
"Very peaceful stay in the mountains. Would book again!"
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)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
The price is AED 485
AED 1,409 total
includes taxes & fees
4 May - 5 May
Woodsy Retreat with a Hot Tub and Seasonal Views!
Laurel Cottage in the heart of Harpers Ferry
Outdoor dining

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!
Interior

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 1,533 total
includes taxes & fees
5 May - 6 May
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 871 total
includes taxes & fees
8 May - 9 May
Firehouse Cottage | Walk to all of downtown HF
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (118)
"The hosts are wonderful. I had a great time in their cozy, clean and beautiful place. Highly recommend for a visit to beautiful and historic WV.I particularly appreciated their fondness for dogs. Mine had a great time too!"
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)
"Very well decorated. The owners were very attentive and kind. Left a candle with wine in the bedrooms. Very well set up and beautiful!!"
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, (25)
"Really enjoyed stay home was great "
The price is AED 415
AED 1,408 total
includes taxes & fees
6 May - 7 May
Peaceful Lakefront Cottage with Mountain Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Property grounds

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!
Interior

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
Exterior

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (95)
"Such a unique cabin to enjoy! It was just what we were looking for a relaxing weekend. We will definitely be going back in the spring/summer!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

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

9.6 out of 10, Exceptional, (93)
"Quaint little getaway for the night. Especially beautiful in autumn with the foliage and the season decorations inside the home! "
The price is AED 312
AED 740 total
includes taxes & fees
5 May - 6 May
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields
Exterior detail

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very Good, (27)
"The cabin was very nice"
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.