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Cottages in Middletown

Our top choices for Middletown cottages

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, (15)
"Very nice property with convenient location! Within walking distance of down town. "
$294 nightly
The price is $328
Aug 26 - Aug 27
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (126)
"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
Quaint Mini Cottage in Shepherdstown - Walking Distance
Dining

Quaint Mini Cottage in Shepherdstown - Walking Distance

8.0 out of 10, Very Good, (3)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Quaint Mini Cottage in Shepherdstown - Walking Distance
Cottage w/ Hot Tub and 100-Mile Valley Views!
3 bedrooms, desk, iron/ironing board, free WiFi

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

10.0 out of 10, Exceptional, (18)
"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."
$343 nightly
The price is $382
Sep 4 - Sep 5
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Carrot Top Cottage surrounded by National Park
Exterior

Carrot Top Cottage surrounded by National Park

10.0 out of 10, Exceptional, (43)
"We had a great family trip here! Close to everything that Harper’s Ferry has to offer! Highly recommend this cute cabin for your trip!"
Carrot Top Cottage surrounded by National Park
Raspberry Retreat Cottage
Outdoor dining

Raspberry Retreat Cottage

10.0 out of 10, Exceptional, (1)
"The cutest cottage ever!! Totally loved this place. Clean, quiet, well decorated and cozy. Just what we were looking for. Don’t sleep on this home! Hosts are very responsive, too. "
Raspberry Retreat Cottage
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (49)
"The house was clean and the beds were very comfortable! Great stay overall "
$215 nightly
The price is $228
Aug 26 - Aug 27
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Lovettsville Cottage in Heart of Wine Country
TV, Netflix, streaming services

Lovettsville Cottage in Heart of Wine Country

9.8 out of 10, Exceptional, (34)
"We stayed here for a few days over the Thanksgiving holiday. It was cozy, comfortable, and had all the great comforts of a home away from home. "
Lovettsville Cottage in Heart of Wine Country
Woodsy Retreat with a Hot Tub and Seasonal Views!
3 bedrooms, desk, free WiFi, bed sheets

Woodsy Retreat with a Hot Tub and Seasonal Views!

9.8 out of 10, Exceptional, (21)
"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."
$305 nightly
The price is $340
Aug 27 - Aug 28
Total with taxes and fees
Woodsy Retreat with a Hot Tub and Seasonal Views!
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, (5)
"The property was charming, clean, and easy to access. It made my stay at Fort Fredrick State Park for the Market Fair very cost-effective, with clean, private accommodations to come home to at night. Well worth the price!"
$169 nightly
The price is $188
Aug 26 - Aug 27
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
ROMANTIC GETAWAY! Heated Spa - Open Year Round!
Property grounds

ROMANTIC GETAWAY! Heated Spa - Open Year Round!

10.0 out of 10, Exceptional, (142)
"We will be back! The guest house was perfect for us! "
ROMANTIC GETAWAY! Heated Spa - Open Year Round!
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, (3)
"Very nice place .Quiet and peaceful"
$210 nightly
The price is $223
Aug 26 - Aug 27
Total with taxes and fees
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
4 bedrooms, desk, free WiFi, bed sheets

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

10.0 out of 10, Exceptional, (22)
"Loved this house for relaxing, enjoying nature and reconnecting with friends!"
$510 nightly
The price is $568
Aug 28 - Aug 29
Total with taxes and fees
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
C&O Canal Potomac River Cottage
Terrace/patio

C&O Canal Potomac River Cottage

10.0 out of 10, Exceptional, (53)
"Looking for something unique and historical -this is the place. Great home base to visit Harper’s Ferry and Antietam. Wish we could have stayed longer!!"
C&O Canal Potomac River Cottage
Hilltop @ Shiloh Summ
Property grounds

Hilltop @ Shiloh Summ

10.0 out of 10, Exceptional, (2)
"Love the location was very nice and quiet "
Hilltop @ Shiloh Summ
Cozy Mountain Cottage - Perfect for Friends, Family
Exterior

Cozy Mountain Cottage - Perfect for Friends, Family

10.0 out of 10, Exceptional, (14)
"We had a great time over Thanksgiving. The house , yard and host were all great. I woood definitely stay here again. "
Cozy Mountain Cottage - Perfect for Friends, Family
Bear Mountain Cottage
Interior

Bear Mountain Cottage

10.0 out of 10, Exceptional, (11)
"This place is beautiful, the owners are awesome, we were allowed to come up a night early due to an incoming winter storm. The owners were so helpful, i cant say enough about them."
Bear Mountain Cottage
Hilltop Cottage @ Shiloh
Property grounds

Hilltop Cottage @ Shiloh

10.0 out of 10, Exceptional, (1)
"Wonderful accommodations!! Everything you could hope hope and then some!! Highly recommend!!! A"
Hilltop Cottage @ Shiloh
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
Modern Country Cottage in Wine Country
Fridge, microwave, oven, stovetop

Modern Country Cottage in Wine Country

8.8 out of 10, Excellent, (3)
"Description of property was accurate. It worked well for our purpose. Location was.close to Leesburg and easy to get to. Mice"
Modern Country Cottage in Wine Country
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 Middletown Hotel Reviews

Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG

10/10 Excellent
"Larry at the desk took my reservations. We booked two rooms to attend a local wedding and he was extremely helpful in securing the rooms as well as getting us in a little early. He assisted with info regarding distance to the venue and was kind and personable when we checked in. The rooms/facility were so clean and updated. Breakfast was delicious. I highly recommend this hotel."
Sandra 1-night trip
Posted 21 hours ago
Holiday Inn Express & Suites Leesburg - Historic District by IHG