Middletown Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Middletown holiday rentals

Fridge, microwave, oven, stovetop

Dog-Friendly Cottage w Playground, Grill & Games

Dog-Friendly Cottage w Playground, Grill & Games
Middletown
9.6 out of 10, Exceptional, (16 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
The price is HK$1,258
HK$2,263 total
includes taxes & fees
4 Mar - 5 Mar
Dog-Friendly Cottage w Playground, Grill & Games
Terrace/patio

Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
9.8 out of 10, Exceptional, (24 reviews)
"We absolutely loved this place! The glamper had everything we needed and more! The hot tub was super relaxing and the host is super responsive! Would definitely stay here again in the future."
United States
Anonymous traveller
The price is HK$817
HK$1,782 total
includes taxes & fees
25 Mar - 26 Mar
Large Glamper w/ Hot Tub and full bathroom-sleep 6
Smart TV, stereo

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (62 reviews)
"Cute little cottage with beautiful views. The hot tub and fire pit were a great bonus. We will come back!"
United States
Paul T.
The price is HK$544
HK$1,851 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Retreat - Hot tub + Mountain Views + Pets
Outdoor spa tub

The Zen Garden by Zen Living

The Zen Garden by Zen Living
Page County
9.6 out of 10, Exceptional, (15 reviews)
"King size bed, fenced yard for our dog, and good mid-week price are what made us choose this place for a short get away. It really suited our needs and we'll be back! Bed was comfortable. House was clean, nicely decorated, and felt welcoming. Could not get WiFi to work, but our cell phone reception was fine."
United States
Joyce F.
The price is HK$902
HK$2,321 total
includes taxes & fees
6 Mar - 7 Mar
The Zen Garden by Zen Living
Property grounds

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.2 out of 10, Wonderful, (17 reviews)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is HK$774
HK$1,674 total
includes taxes & fees
8 Mar - 9 Mar
Peaceful Retreat on Creekside
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is HK$1,056
HK$1,706 total
includes taxes & fees
4 Mar - 5 Mar
Mountain View Bungalow in Front Royal
Outdoor spa tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
The price is HK$957
HK$2,652 total
includes taxes & fees
10 Mar - 11 Mar
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Exterior

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Stephens City
9.4 out of 10, Exceptional, (8 reviews)
"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "
United States
Maureen W.
The price is HK$931
HK$2,374 total
includes taxes & fees
5 Mar - 6 Mar
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Terrace/patio

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (2 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is HK$1,021
HK$1,281 total
includes taxes & fees
26 Mar - 27 Mar
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stayed "
United States
Mike F.
The price is HK$1,056
HK$1,769 total
includes taxes & fees
9 Mar - 10 Mar
Apple Mountain Retreat
Interior

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Luray
9.6 out of 10, Exceptional, (72 reviews)
"Very nice place and very well set up and welcoming."
United States
Adam Y.
The price is HK$1,027
HK$2,417 total
includes taxes & fees
8 Mar - 9 Mar
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities
Exterior

Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!

Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Luray
9.6 out of 10, Exceptional, (12 reviews)
"Great stay, very quiet. Everything was in place to ensure a comfortable stay. Perfect getaway for a couple of days and within 15 minutes to town. "
United States
Derek B.
The price is HK$1,019
HK$2,599 total
includes taxes & fees
4 Mar - 5 Mar
Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Smart TV, fireplace, books

Cozy 2-bedroom house in fantastic Luray with AC

Cozy 2-bedroom house in fantastic Luray with AC
Luray
The price is HK$873
HK$2,387 total
includes taxes & fees
4 Mar - 5 Mar
Cozy 2-bedroom house in fantastic Luray with AC
Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (30 reviews)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is HK$1,486
HK$1,838 total
includes taxes & fees
4 Mar - 5 Mar
Blue Mountain Cabin, secluded, perfect for couples, near main road
Interior

Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View

Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View
Rileyville
10.0 out of 10, Exceptional, (4 reviews)
"The property is lovely. It has all the needs for a family, and is very well located for hikes and visits to vineyards in the area. Will definitely visit again (this is our second stay)."
United States
Jonathan H.
The price is HK$1,061
HK$2,856 total
includes taxes & fees
11 Mar - 12 Mar
Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View
Dining

Completely private suite with tub,kitchen, living room, & private entrance

Completely private suite with tub,kitchen, living room, & private entrance
Washington
10.0 out of 10, Exceptional, (19 reviews)
"Very nice well kept property"
United States
Anonymous traveller
The price is HK$1,017
HK$1,771 total
includes taxes & fees
17 Mar - 18 Mar
Completely private suite with tub,kitchen, living room, & private entrance
Interior

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very good, (1 review)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
The price is HK$704
HK$2,224 total
includes taxes & fees
4 Mar - 5 Mar
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Property grounds

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
Front Royal
10.0 out of 10, Exceptional, (16 reviews)
"We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!"
United States
Dan P.
The price is HK$1,118
HK$3,139 total
includes taxes & fees
8 Mar - 9 Mar
The Vue - Mountain Top hot tub overlooking the Shenandoah River
Pool

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville
10.0 out of 10, Exceptional, (347 reviews)
"Everything was perfect for our stay. "
United States
Debbie O.
The price is HK$1,373
HK$2,367 total
includes taxes & fees
17 Mar - 18 Mar
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Property grounds

Private Cabin in the woods w/ firepit right next to Shenandoah River

Private Cabin in the woods w/ firepit right next to Shenandoah River
Bentonville
10.0 out of 10, Exceptional, (33 reviews)
"We had such a wonderful experience at this booking. Our hosts were thoughtful in their hospitality, providing everything guests would need for a few nights accommodations. Unexpected but delightful perks- tons of different coffee maker options, plush throws and blankets everywhere, modern but still rustic decor. It was truly spectacular and we absolutely recommend that you choose this cabin "
United States
Deborah L.
The price is HK$1,244
HK$2,657 total
includes taxes & fees
4 Mar - 5 Mar
Private Cabin in the woods w/ firepit right next to Shenandoah River
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

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

10/10 Excellent
"This is my go-to hotel in Winchester. The rooms are very comfortable and clean. The staff is great. It is close to many restaurants and stores. And its location is the shortest drive to the Summit Point Motor Sports Park. A win-win."
Scott 2-night trip
Posted 13 hours ago
SpringHill Suites by Marriott Winchester

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middletown has a good selection of bars and the restaurants. Make sure you have time to check out the entertainment choices and churches during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Secluded River Cabin Getaway (Masten Cabin): This holiday home rental outside of Middletown is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Middletown?

Shenandoah River and Cedar Creek and Belle Grove National Historical Park are a couple of lovely local spots to get outside and enjoy nature. While here, Belle Grove Plantation and Cedar Creek Battlefield Foundation are other places worth a visit.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.