Holiday Homes in Middletown

  • 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
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Middletown holiday homes

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 €236
includes taxes & fees
3 Feb - 4 Feb
Mountain retreat w/hot tub, sauna, projector, close to river and 25 to NP!
Property grounds

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (22 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is €256
includes taxes & fees
3 Feb - 4 Feb
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Terrace/patio

Screened Porch w/Swing, Fire Pit, Grill & Deck

Screened Porch w/Swing, Fire Pit, Grill & Deck
Luray
10.0 out of 10, Exceptional, (1 review)
"We loved our stay at this cabin. It has a great feeling of being out in nature as a cabin but with a feel of a newly renovated and quality interior. We took advantage of the screened in porch for morning coffee and evening relaxing with the family. It's a great feature of this house. The kitchen was great and had everything we needed during our stay. The grill I think may have been brand new and worked flawlessly. One reason we stayed here was the access to the river. It was a little further...
United States
Chris P.
The price is €293
includes taxes & fees
8 Feb - 9 Feb
Screened Porch w/Swing, Fire Pit, Grill & Deck
Smart TV

Welcome to the Ladybug Retreat!

Welcome to the Ladybug Retreat!
Boyce
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
The price is €340
includes taxes & fees
3 Feb - 4 Feb
Welcome to the Ladybug Retreat!
Fridge, microwave, oven, stovetop

Yurt w/hot tub & fire pit

Yurt w/hot tub & fire pit
Wardensville
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful little place in the wilderness. Tony was a great host from check-in to checkout periodically checked in to make sure we had a good experience. "
United States
syed r.
The price is €248
includes taxes & fees
3 Feb - 4 Feb
Yurt w/hot tub & fire pit
Property grounds

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.2 out of 10, Wonderful, (17 reviews)
"We had a great getaway to the mountains "
United States
Andrea R.
The price is €182
includes taxes & fees
3 Feb - 4 Feb
Peaceful Retreat on Creekside
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 €259
includes taxes & fees
9 Feb - 10 Feb
Cozy 2-bedroom house in fantastic Luray with AC
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (13 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 €189
includes taxes & fees
3 Feb - 4 Feb
Mountain View Bungalow in Front Royal
Outdoor dining

Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (204 reviews)
"This was our 3rd stay and as always it was perfect. Already can’t wait to come back "
United States
Jess E.
The price is €249
includes taxes & fees
4 Mar - 5 Mar
Cozy Lakeside Homestead
Smart TV, table football, books

Modern~OutdoorCinema~HotTub~EVSE

Modern~OutdoorCinema~HotTub~EVSE
Rileyville
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place!"
United States
Carmen P.
The price is €361
includes taxes & fees
9 Feb - 10 Feb
Modern~OutdoorCinema~HotTub~EVSE
Dining

Private Colonial 3BR House with tub,kitchen, Fast Wi-Fi 2 min from the Inn!

Private Colonial 3BR House with tub,kitchen, Fast Wi-Fi 2 min from the Inn!
Washington
10.0 out of 10, Exceptional, (121 reviews)
"Excellent location!"
United States
Elisa L.
The price is €234
includes taxes & fees
9 Feb - 10 Feb
Private Colonial 3BR House with tub,kitchen, Fast Wi-Fi 2 min from the Inn!
Fridge, microwave, oven, stovetop

Cozy Wooded Cabin by National Park, EV Charger

Cozy Wooded Cabin by National Park, EV Charger
Star Tannery
10.0 out of 10, Exceptional, (6 reviews)
"This home was very secluded and had beautiful views. The interior was a perfect mix of historic and modern touches. Hosts were very responsive and we would stay here again!"
United States
Cyndi B.
The price is €314
includes taxes & fees
3 Feb - 4 Feb
Cozy Wooded Cabin by National Park, EV Charger
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is €272
includes taxes & fees
15 Feb - 16 Feb
Newly renovated Farm cottage with Mountain views
Outdoor spa tub

Hideaway Mountain Cabin

Hideaway Mountain Cabin
Rileyville
10.0 out of 10, Exceptional, (12 reviews)
"Loved it. Private and quiet with a great view. Bring your 4 x 4 truck/SUV"
United States
George C.
The price is €343
includes taxes & fees
9 Feb - 10 Feb
Hideaway Mountain Cabin
Exterior

Beautiful Comfortable House w/ Fireplace

Beautiful Comfortable House w/ Fireplace
Woodstock
9.4 out of 10, Exceptional, (11 reviews)
"It’s mostly ok but first floor bathroom was very dirty and kitchen wasn’t that clean we was very despoint"
United States
Myong L.
The price is €259
includes taxes & fees
9 Feb - 10 Feb
Beautiful Comfortable House w/ Fireplace
Outdoor spa tub

Shenandoah Mountain Cabin

Shenandoah Mountain Cabin
Rileyville
10.0 out of 10, Exceptional, (20 reviews)
"This cabin was spacious and yet cozy. It had everything we needed for a short stay, and the peace and quiet was so nice. The cabin in well kept too. The view was amazing. We took a short road trip to a nearby town. The host was fantastic and we hope to stay at one their properties again. "
United States
Katie B.
The price is €348
includes taxes & fees
8 Feb - 9 Feb
Shenandoah Mountain Cabin
Exterior

NEW! The Hilltop Station

NEW! The Hilltop Station
Rileyville
8.0 out of 10, Very good, (2 reviews)
"Our stay was absolutely beautiful, between the cleanliness of the property, great communication with the owner (we decided to stay another day!), the train coming by at 9pm & 11pm, (it didn’t bother us, were used to trains being so close at night, the kids even loved it), to the beautiful scenario. The driveway was pretty steep I had to call and make sure it was the right way, while my aunt just passed it and had to call me. But all in all this house was a great stay! Definitely recommend!"
United States
Devyn W.
The price is €366
includes taxes & fees
3 Feb - 4 Feb
NEW! The Hilltop Station
Exterior

Big Sunny Family House

Big Sunny Family House
Front Royal
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
Big Sunny Family House
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 €372
includes taxes & fees
3 Feb - 4 Feb
Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View
TV, offices

Mountain cottage w/hot tub & fire pit

Mountain cottage w/hot tub & fire pit
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is €267
includes taxes & fees
5 Feb - 6 Feb
Mountain cottage w/hot tub & 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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. "
Gerald 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
560
Accommodation
175 Holiday Homes
Lowest Price
€182
Highest Price
€372