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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 61 Cottages in Middletown with updated reviews, rates, and availability.

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Private kitchen

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (30)
"This is a beautiful, tasteful, updated home. I was surprised at how comfortable the beds were! It's in a great location, and we appreciated the prompt and thoughtful host communication. It's very reasonably priced for all that you get with this stay! Parking was tricky for us as we rented on the night of street sweeping and had to park several blocks away. Other than that, this is an excellent place to stay. "
The price is AED 488
AED 1,024 total
includes taxes & fees
3 Feb - 4 Feb
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (32)
"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
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Terrace/patio

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 Feb - 14 Feb
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
Exterior

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond
The Carriage House at Carrot Top Cottage
Terrace/patio

The Carriage House at Carrot Top Cottage

9.8 out of 10, Exceptional, (30)
"We had a wonderful stay at the Carriage House. It was very comfortable. The location is perfectfor exploring historic Harper’s Ferry and the hiking trails. "
The Carriage House at Carrot Top Cottage
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!!"
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Royal Heritage Home @ Historic Leesburg
Living area

Royal Heritage Home @ Historic Leesburg

9.8 out of 10, Exceptional, (24)
"We stayed at this property during our annual visit to Leesburg. We enjoy the downtown area (easy to walk) and catching an Uber to the local vineyards! House was perfect for our group of 5. Majority of our time at the house was spent sleeping, but we all felt comfortable and had enough space. Three bathrooms were great! "
The price is AED 775
AED 1,719 total
includes taxes & fees
18 Feb - 19 Feb
Royal Heritage Home @ Historic Leesburg
Lovettsville Cottage in Heart of Wine Country
Lovettville Vacation Rental | 1BR | 2BA | 2 Stories | 3 Steps Required

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (32)
"Perfect for the weekend getaway we were looking for! Beautiful guest home that was very clean and was well stocked with anything we might need. Only one issue was there were lots of stink bugs in the house but I imagine in the winter that would be more of a problem then in the warmer months. "
Lovettsville Cottage in Heart of Wine Country
Close to Hiking | Hot Tub | Fire Pit | Pets OK
Our deck is great for relaxing and enjoying the outdoors

Close to Hiking | Hot Tub | Fire Pit | Pets OK

9.0 out of 10, Wonderful, (2)
"Me and my friends had a great stay here, even though we did have some trouble with our cars in the snow the owners were very responsive and helpful. The hot tub was great, and everything worked as it should’ve! We would definitely come again! "
Close to Hiking | Hot Tub | Fire Pit | Pets OK
RIVERKEEPER INN, Waterfront Property on the Potomac River
Private Waterfront Deck with swing goes with rental

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (116)
"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
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 492
AED 1,777 total
includes taxes & fees
6 Feb - 7 Feb
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Lake View Retreat - Cottage Near a Peaceful Lake!
This home is just a short walk to Lake Shannondale, and has wintertime views of the lake! Spend your mornings on the front porch, or take a leisurely stroll around the lake.

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 367
AED 1,303 total
includes taxes & fees
6 Feb - 7 Feb
Lake View Retreat - Cottage Near a Peaceful Lake!
Peaceful Lakefront Cottage with Mountain Views!
Enjoy a soak in the hot tub!

Peaceful Lakefront Cottage with Mountain Views!

10.0 out of 10, Exceptional, (22)
"Although short, we had a wonderful stay. Beautiful house with amazing views. Great communication with property host. Cant wait to come back! Thank you for hosting us last minute! "
The price is AED 481
AED 1,503 total
includes taxes & fees
6 Feb - 7 Feb
Peaceful Lakefront Cottage with Mountain Views!
Cottage at Gray Fox- Many Attraction- Pet Friendly
Private kitchen

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
Bear Mountain Cottage
Exterior

Bear Mountain Cottage

10.0 out of 10, Exceptional, (7)
"A friend and I stayed in this modern cottage, tucked away in the woods about 10 minutes outside Leesburg's historic downtown. It has 1 bedroom (King) and a sitting room with a daybed, which would be a very cozy sleep for two (and I don't believe there was a door to close off the room). We shared the king and was glad another couple didn't join us, as it would have been quite tight sleeping. Also the one bathroom is shared so that creates some noise between the rooms. For two people, however,...
Bear Mountain Cottage
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, (14)
"The view of this house is amazing! Absolutely beautiful!"
The price is AED 422
AED 1,468 total
includes taxes & fees
6 Feb - 7 Feb
Cottage w/ Hot Tub and 100-Mile Valley Views!
Magical Treehouse in Woods, Close many Wineries & Breweries, Pet Friendly!
Exterior

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!
Woodsy Retreat with a Hot Tub and Seasonal Views!
Living area

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (17)
"We love it! everything was perfect 🤗 we definitely coming back ❤️"
The price is AED 419
AED 1,325 total
includes taxes & fees
6 Feb - 7 Feb
Woodsy Retreat with a Hot Tub and Seasonal Views!
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!
Exterior

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

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

10.0 out of 10, Exceptional, (2)
"Very cozy house and I didn’t have to bring anything , the owners really supplied everything I needed and the dock was right there, looking to catch fish go left down the river and go early morning"
The price is AED 275
AED 592 total
includes taxes & fees
2 Feb - 3 Feb
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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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, (90)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Welcome!

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

9.6 out of 10, Exceptional, (88)
"It is a very quaint property and sed has the rustic cabin feel, the location was not as intimate as we hoped as it is in a regular neighborhood with close primary with neighbors. "
The price is AED 312
AED 751 total
includes taxes & fees
2 Feb - 3 Feb
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very Good, (26)
"This was a lovely getaway for me and my girlfriend. There were a few issues: the cabin could use a good dusting in kind of obvious spaces, host told us the cleaners hadn’t been in halfway through and that was a tad disconcerting, and I don’t think the listing mentioned how the cabin is so close to the main property. We think the privacy was still pretty good, but it would’ve been nice had that been clearer up front. Overall, a good stay. "
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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