A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Search Middletown Cottage Rentals from CA $286

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Middletown cottages

A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is CA $208
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

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, (16 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 $409
CA $551 total
includes taxes & fees
Nov 8 - Nov 9
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

3. Mountain View Cottage with Hot Tub and River Views

Mountain View Cottage with Hot Tub and River Views
Front Royal
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...
United States
MaryBeth C.
The price is CA $345
CA $743 total
includes taxes & fees
Dec 7 - Dec 8
Mountain View Cottage with Hot Tub and River Views
A wooden deck with a glass railing overlooking a forested area.

4. Round House w Mountain View Hot Tub

Round House w Mountain View Hot Tub
Luray
10.0 out of 10, Exceptional, (1 review)
The price is CA $182
CA $409 total
includes taxes & fees
Nov 16 - Nov 17
Round House w Mountain View Hot Tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

5. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
United States
Kevin D.
The price is CA $435
CA $810 total
includes taxes & fees
Nov 9 - Nov 10
Mountaintop Cottage | Private Hot Tub
A hot tub on an outdoor deck with a view of trees and hills.

6. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is CA $513
CA $900 total
includes taxes & fees
Nov 8 - Nov 9
Mountain View Cottage | Hot Tub & Game Room
An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

7. 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 $245
CA $459 total
includes taxes & fees
Nov 9 - Nov 10
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A covered porch with a table and chairs, large windows, and a ceiling fan.

8. 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 $581
CA $664 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"I was blown away by the welcome we received—the front desk receptionist couldn’t have been better. She is GREAT at her job. This is our first time at a Spark hotel, so I didn’t know what to expect. We booked the suite because it looked like it was a separate room with a real door, but I wasn’t holding my breath because that sort of thing is almost IMPOSSIBLE to find nowadays in a low- to mid-priced hotel. I was thrilled that it is an entirely separate room…Yay!!! The room was comfortable, HUGE, clean, and had wonderful lighting. We were so super-comfortable here, and will seek out Spark hotels in the future!"
Mary Ann 1-night trip
Posted 2 hours ago
Spark by Hilton Winchester

Find out more about Middletown

Middletown Cottages information

Number of reviews
62
Accommodation
54 Cottages
Lowest Price
CA $286
Highest Price
CA $900

Frequently asked questions

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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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