A large house in a field with a cloudy sky.

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Middletown cottages

Exterior

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$205 nightly
The price is $226
Aug 3 - Aug 4
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Outdoor spa tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
$392 nightly
The price is $436
Jul 26 - Jul 27
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Terrace/patio

Apple Mountain House | Hot Tub | Game Room

Apple Mountain House | Hot Tub | Game Room
Front Royal
9.6 out of 10, Exceptional, (14 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
$465 nightly
The price is $513
Jul 26 - Jul 27
Total with taxes and fees
Apple Mountain House | Hot Tub | Game Room
Terrace/patio

All-Inclusive 4BR | Mountain Views | Hot Tub

All-Inclusive 4BR | Mountain Views | Hot Tub
Front Royal
$504 nightly
The price is $556
Aug 18 - Aug 19
Total with taxes and fees
All-Inclusive 4BR | Mountain Views | Hot Tub
Outdoor spa tub

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (70 reviews)
"We enjoyed the hot tub, the views, and the easy check in/check out."
United States
Dakota B.
$235 nightly
The price is $260
Jul 26 - Jul 27
Total with taxes and fees
Cozy Retreat - Hot tub + Mountain Views + Pets
Terrace/patio

The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"Amazing location! Clean and well kept! Wonderful experience!"
United States
Kaylyn K.
$594 nightly
The price is $655
Aug 17 - Aug 18
Total with taxes and fees
The VUE | Mountaintop 4BR | Hot Tub & Views
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"convenient location for stopping during my trips"
Arthur 1-night trip
Posted 5 hours ago
Fairfield Inn & Suites by Marriott Winchester

Find out more about Middletown

Middletown Cottages information

Number of reviews
69
Accommodation
54 Cottages
Lowest Price
$226
Highest Price
$655

Frequently asked questions

Why book your cottage in Middletown with Expedia?
Expedia has some wonderful cottages in Middletown, so start packing your bags for an unforgettable vacay on nature's doorstep. If you have a budget, choose how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with free WiFi or a pool. We'll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Middletown?
With Expedia's handy filter tool, comparing cheap cottages in Middletown is easy. To view properties that are friendly on the wallet, refine your search by star rating, budget and amenities.
What is there to do in Middletown near my cottage?
After you've unpacked your bags and settled in, get out and discover the incredible things Middletown has for you to experience. Belle Grove Plantation is a great attraction to add to your must-do list.

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