A large house in a field with a cloudy sky.

Search Middletown Cottage Rentals from CA $464

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middletown cottages

Exterior

1. 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.
The price is CA $206
CA $310 total
includes taxes & fees
Aug 23 - Aug 24
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Outdoor spa tub

2. 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
The price is CA $406
CA $601 total
includes taxes & fees
Aug 20 - Aug 21
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Coffee/tea maker, fridge, microwave, stovetop

3. ‘Sweet Dreams' Cozy Cottage in Downtown Winchester

‘Sweet Dreams' Cozy Cottage in Downtown Winchester
Winchester
The price is CA $124
CA $217 total
includes taxes & fees
Aug 23 - Aug 24
‘Sweet Dreams' Cozy Cottage in Downtown Winchester
Terrace/patio

4. Mountain-View Cottage | Hot Tub & River Views

Mountain-View Cottage | Hot Tub & River Views
Front Royal
The price is CA $259
CA $725 total
includes taxes & fees
Aug 23 - Aug 24
Mountain-View Cottage | Hot Tub & River Views
Terrace/patio

5. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.6 out of 10, Exceptional, (15 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is CA $261
CA $731 total
includes taxes & fees
Sep 1 - Sep 2
Mountain View Cottage | Hot Tub & Game Room
Terrace/patio

6. The VUE | Mountaintop 4BR | Hot Tub & Views

The VUE | Mountaintop 4BR | Hot Tub & Views
Front Royal
10.0 out of 10, Exceptional, (24 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
The price is CA $469
CA $898 total
includes taxes & fees
Aug 23 - Aug 24
The VUE | Mountaintop 4BR | Hot Tub & Views
Property grounds

7. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Front Royal
The price is CA $291
CA $349 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
Outdoor spa tub

8. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.8 out of 10, Exceptional, (37 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is CA $550
CA $1,087 total
includes taxes & fees
Sep 3 - Sep 4
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
House (2 Bedrooms) | Interior

9. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
The price is CA $250
CA $464 total
includes taxes & fees
Aug 20 - Aug 21
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

10/10 Excellent
"The checkin was super quick. The room was not only clean it smelled fresh. The executive suite easily slept 6. Super quiet and cool. The bathroom was extremely clean too. Lots of towels. Maybe a couple Xtra lotions/soaps would be nice but it wasn't a big deal."
Crystal 1-night trip
Posted 8 hours ago
Courtyard by Marriott Winchester

Find out more about Middletown

Middletown Cottages information

Number of reviews
Accommodation
53 Cottages
Lowest Price
CA $464
Highest Price
CA $464

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.

Explore a world of travel with Expedia