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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Middletown cottages

Exterior

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is €143
includes taxes & fees
7 Apr - 8 Apr
Bring Your Own Boat - Meticulously restored house on the Potomac River
Interior

Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is €371
includes taxes & fees
20 Mar - 21 Mar
Rural & Historic Detour Escape w/ Horses On-site!
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (64 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is €225
includes taxes & fees
23 Mar - 24 Mar
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Outdoor spa tub

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

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"Great view, very secluded"
United States
Matt s.
Cottage w/ Hot Tub and 100-Mile Valley Views!
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
Lake View Retreat - Cottage Near a Peaceful Lake!
Outdoor dining

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (24 reviews)
"Lovely views, very spacious, well appointed in terms of kitchen."
United States
sharyn m.
The price is €382
includes taxes & fees
25 Mar - 26 Mar
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (23 reviews)
"Great house and location! "
United States
Johanna S.
The price is €260
includes taxes & fees
12 Mar - 13 Mar
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Terrace/patio

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

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is €338
includes taxes & fees
12 Mar - 13 Mar
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (46 reviews)
"We enjoyed the stay and it was an easy walk to the places we wanted to go!"
United States
Mike S.
The price is €158
includes taxes & fees
6 Apr - 7 Apr
The Carriage House at Carrot Top Cottage
Fridge, microwave, oven, stovetop

Royal Heritage Home @ Historic Leesburg

Royal Heritage Home @ Historic Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (40 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is €462
includes taxes & fees
12 Mar - 13 Mar
Royal Heritage Home @ Historic Leesburg
Exterior

Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area

Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area
Paeonian Springs
The price is €391
includes taxes & fees
16 Mar - 17 Mar
Cozy Haven Cottage - Wedding and Winery Retreat - Leesburg/Purcellville Area
Exterior

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (25 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is €289
includes taxes & fees
18 Mar - 19 Mar
Woodsy Retreat with a Hot Tub and Seasonal Views!
Terrace/patio

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
The price is €449
includes taxes & fees
29 Mar - 30 Mar
Peaceful Lakefront Cottage with Mountain Views!
Exterior

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"We had a great stay "
United States
Lauren O.
The price is €600
includes taxes & fees
12 Mar - 13 Mar
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
House (Multiple Bedrooms) | Interior

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is €1,572
includes taxes & fees
12 Mar - 13 Mar
'thomson Farm' Classic Home < 10 Mi to Vineyards!
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

Best Western Historic Frederick

Best Western Historic Frederick

8/10 Good
" Nice hotel for a stay close to downtown. The staff are friendly and caring and the breakfast is above average. "
Pamela 1-night trip
Posted 22 hours ago
Best Western Historic Frederick

Find out more about Middletown

Middletown Cottages information

Number of reviews
327
Accommodation
84 Cottages
Lowest Price
€143
Highest Price
€1,572

Frequently asked questions

Why book your cottage in Middletown with Expedia?
Reserving a cottage in Middletown is as simple as working out your travel dates and picking your ideal place for outdoor recreation and relaxation. From luxurious retreats to inexpensive properties and cottages that offer amenities like a kitchenette, Expedia has something for all traveller tastes. As for terrific deals? We've have them as well!
How can I find cheap cottages in Middletown?
With Expedia's helpful filter tool, booking cheap cottages in Middletown is a cinch. To find stays that are friendly on the wallet, narrow your search by star rating, amenities and budget.
What is there to do in Middletown near my cottage?
If you're ready to fill up your itinerary in Middletown, check out Maryland National Golf Club. It's a winner with locals and travellers alike.