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Search Middletown Cottage Rentals from CA $128

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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Middletown Cottages

Secluded, Cozy Cottage in the Shenandoah Valley
Relax in a serene outdoor space under a sheltered pergola with a beautiful forest view.

Secluded, Cozy Cottage in the Shenandoah Valley

10.0 out of 10, Exceptional, (180)
"A real cute place with a cozy layout and amazing bathroom and shower. It was just secluded enough but not overly challenging to get to. The upper porch was great for hanging out and watching the pair of hummingbirds that seem to have made the area home. The bed was comfortable but also a little squeaky and noisy. We really enjoyed our stay and it was just the relaxing getaway we needed. "
Secluded, Cozy Cottage in the Shenandoah Valley
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Enjoy a romantic dinner for two under a charming pergola, complete with a wine bottle and glasses.

Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi

9.8 out of 10, Exceptional, (28)
"So much to do in the area, cute little cottage, very clean and comfortable "
Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi
Hunt Country cottage in Upperville!
Kitchen features a large sink, dishwasher, microwave, and stove, with a cozy seating area and window offering a view of the outdoors.

Hunt Country cottage in Upperville!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay and look forward to booking again next year!"
Hunt Country cottage in Upperville!
Historical cottage in the town of Paris
Stroll up to the charming entrance, flanked by windows, and enjoy the serene surroundings of this two-story home.

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
Cozy Retreat - Hot tub + Mountain Views + Pets
Enjoy a serene view of the surrounding landscape from the comfort of this room, featuring a ceiling fan, table, chairs, and a cozy bench.

Cozy Retreat - Hot tub + Mountain Views + Pets

9.8 out of 10, Exceptional, (46)
"It’s was a beautiful stay for me and my partner we got to spend quality time together "
The price is CA $128
CA $377 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Retreat - Hot tub + Mountain Views + Pets
Weekend getaway short distance from DC/Northern Virginia
Stunning two-story house with a symmetrical facade, steeply pitched roof, and central chimney, set amidst a well-manicured lawn and rolling hills.

Weekend getaway short distance from DC/Northern Virginia

10.0 out of 10, Exceptional, (86)
"This place was cozy and welcoming, exactly what we were looking for on a weekend away."
Weekend getaway short distance from DC/Northern Virginia
Front Royal Retreat ~ 1 Mi to National Park!
Enjoy cooking in this well-lit kitchen with a central island and essential appliances.

Front Royal Retreat ~ 1 Mi to National Park!

3.0 star property
Front Royal Retreat ~ 1 Mi to National Park!
Mountain Town Adventures Home w/ Fire Pit!
Cozy up by the fireplace and enjoy meals in the dining area with a view of the outdoor patio.

Mountain Town Adventures Home w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was fantastic"
Mountain Town Adventures Home w/ Fire Pit!
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Enjoy a well-equipped kitchen and dining area with a refrigerator, oven, and sink, perfect for meal preparation and dining.

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

9.8 out of 10, Exceptional, (12)
"We loved the property and the access to the river."
The price is CA $343
CA $518 total
includes taxes & fees
Aug 5 - Aug 6
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Sunny Front Royal Vacation Rental w/ Hot Tub!
Spacious room with a round dining table and unique spiral staircase.

Sunny Front Royal Vacation Rental w/ Hot Tub!

3.0 star property
Sunny Front Royal Vacation Rental w/ Hot Tub!
Country Elegance overlooking the Shenandoah River
Relax in a serene outdoor oasis with a hot tub surrounded by lush greenery and a wooden pergola.

Country Elegance overlooking the Shenandoah River

10.0 out of 10, Exceptional, (104)
"It was so relaxing & beautiful! We loved the views from every room , even the bathroom upstairs! "
Country Elegance overlooking the Shenandoah River
Chic Front Royal Retreat Near Shenandoah River!
House (2 Bedrooms) | Interior

Chic Front Royal Retreat Near Shenandoah River!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Nice place near skyline drive"
Chic Front Royal Retreat Near Shenandoah River!
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Relax in this serene sunroom with a brick accent wall, glass coffee table, and comfortable sofa, offering a peaceful view of the surrounding mountains.

Home w/ Hot Tub Near Shenandoah Nat'l Park!

3.0 star property
Home w/ Hot Tub Near Shenandoah Nat'l Park!
Modern Mountain Retreat w/ Deck + Hot Tub!
Kitchen features a dishwasher, oven, microwave, and sink with a window above.

Modern Mountain Retreat w/ Deck + Hot Tub!

3.0 star property
Modern Mountain Retreat w/ Deck + Hot Tub!
Cozy Cabin With Sunroom & Cacapon River Access!
Relax in a spacious room with a high ceiling, ceiling fan, and large window offering a view of the surrounding landscape.

Cozy Cabin With Sunroom & Cacapon River Access!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic family trip. This was a great landing point to amazing outdoor adventures in the area. "
Cozy Cabin With Sunroom & Cacapon River Access!
Spectacular Cottage with Shenandoah River Views
Enjoy cooking in this well-equipped kitchen with a large island and bookshelf.

Spectacular Cottage with Shenandoah River Views

10.0 out of 10, Exceptional, (207)
"We loved our stay here. Came here to escape DC. Very easy to get to. Still close to civilization but still feels remote on the property. 20 minutes from Skyline Drive."
Spectacular Cottage with Shenandoah River Views
Front Royal Hilltop Cabin w/ Panoramic Views!
Relax in a serene hot tub surrounded by a natural landscape.

Front Royal Hilltop Cabin w/ Panoramic Views!

3.0 star property
Front Royal Hilltop Cabin w/ Panoramic Views!
Cozy Home in Star Tannery w/ Private Backyard!
House (2 Bedrooms) | Interior

Cozy Home in Star Tannery w/ Private Backyard!

3.0 star property
Cozy Home in Star Tannery w/ Private Backyard!
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
House (2 Bedrooms) | Interior

Cozy Virginia Escape w/ Deck, Grill & Fire Pit!

2.0 star property
Cozy Virginia Escape w/ Deck, Grill & Fire Pit!
4 season fun & spectacular views, right out the front door.
Relax on the deck with a bench and covered seating area, surrounded by a serene snow-covered field and distant hills.

4 season fun & spectacular views, right out the front door.

9.0 out of 10, Wonderful, (2)
"Great communication with the owner. House was comfortable and had everything needed for a relaxing stay. "
4 season fun & spectacular views, right out the front door.
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

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained. "
Frank 1-night trip
Posted 1 day ago
Comfort Inn & Suites