Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Davis

4.85 out of 5 average rating, 158 reviews

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

ElydiaRating, 5 stars3 months ago

This place was AWESOME! Perfect location for wanting to spend your time on the slopes! Super cozy, very spacious, looks exactly like the pictures. The living area is a great hangout spot and the fireplaces kept us nice and warm during this windy winter stay.

Guest favourite

Cabin in Luray

4.94 out of 5 average rating, 152 reviews

❤️️Wildflower Cabin❤️️ A Luxury Riverfront Retreat

KathyRating, 5 stars5 days ago

The cabin was exactly what I was looking for… river frontage, surrounded by nature, quiet and peaceful. The cabin was very clean and up to date on all amenities. I had no problems at all. I slept better there than I do at home. It was an Excellent getaway! I’ll definitely return someday.

Guest favourite

Home in Elkton

4.95 out of 5 average rating, 185 reviews

Hottub 5 acres, Great hiking,The best views around

JillianRating, 5 stars2 weeks ago

We had a wonderful time at stony creek outlook! The property sits on a mountain with a beautiful view. The house was big enough for the two families we had with kids ranging from 1-6. The hot tub was used every night and loved by the littles (and adults once bedtime came) . The kitchen had everything we needed as we chose to cook most nights. Skyline drive entrance was close, about 20 min. We opted to hike blackrock summit at the recommendation of the host. We were a little concerned with the littles we had but it ended up being perfect distance with a breathtaking view! On the rainy day we had we visited Massanutten waterpark. We enjoyed a fire in the pit on a cold evening. Elkton brewery was a fun spot to have a beer. The biggest hit with the kids were the visits from the neighbors two very friendly dogs, Lily and venture. Although we didn’t bring our own dog, the house was well equipped to bring your dogs own furry friend. Can’t say enough nice things about this place!

Top Guest favourite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 109 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Marissa MarieRating, 5 stars2 weeks ago

we stayed at Alisons place for a girl's weekend. It was beautiful! the pictures are exactly how the place looks, decorated nicely and very very clean. the host communicated very well and quickly, even had alot of recommendations for food and things to do. highly recommend staying here!

Superhost

Cabin in Shenandoah

4.79 out of 5 average rating, 466 reviews

Shenandoah Sunsets~Breathtaking Views~ New Hot Tub

NoraRating, 5 stars5 days ago

This was such a beautiful home. The views were stunning, so quiet and peaceful. House was very clean, huge kitchen and dining space, with a cozy fire place. It's a little off the beaten path, but worth the drive! Culin was a great host, super responsive and had great recommendations for activities and food! All in all it was a great trip!!

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

Spectacular Chalet, Timroc II, close to lake, Wisp

KristinRating, 5 stars7 months ago

Absolutely beautiful home and exceeded our expectations! The pictures don’t do this property justice. From the firepit, to the hot tub, to the basement, and everything in between everything was perfect. Roberta quickly responded anytime we needed anything. Most definitely will be coming here again!

Guest favourite

Cottage in Shenandoah

4.96 out of 5 average rating, 184 reviews

Cozy Cottage Retreat: SNP, Luray Caverns, River

MargaretRating, 5 stars1 month ago

The house itself is cute and perfect for a short stay. The beds are super comfy and the place is nicely decorated. We enjoyed turning the little electric fireplace on in the evening when we were relaxing. FYI…..There is a railroad running directly in front of the house but surprisingly the noise from the train wasn’t that bad and it was kind of cool watching it pass through from time to time. Lastly, I would like to thank Julie for letting us stay at her place for the weekend and for being such a considerate, knowledgeable and caring host!

Guest favourite

Cabin in New Market

4.91 out of 5 average rating, 165 reviews

Sunset Views! Hot Tub! Fireplace! Mountain Escape

JesseRating, 5 stars5 days ago

You get exactly what you see in the pictures and more! We stayed in the hot tub the majority of the time while taking in the scenic view. The rest was in the screened in porch where you still have the view along with hearing nature. The place is amazing and we will back next chance we get!

Holiday rentals for every style

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Popular amenities for Middletown holiday rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Stay near Middletown's top sights

Cedar Creek & Belle Grove National Historical Park7 locals recommend

Shaffer's BBQ & Market8 locals recommend

The Italian Touch3 locals recommend

Other great holiday rentals in Middletown

Guest favourite

Home in McGaheysville

4.82 out of 5 average rating, 11 reviews

Mtn Views~Hot Tub~2 Game Rms~Fire Pit~Pet Friendly

AsmitaRating, 5 stars3 weeks ago

We had a wonderful stay at Masaneuttan’s Airbnb! The space was cozy, clean, and thoughtfully arranged with everything we needed for a comfortable visit. The host was incredibly kind and responsive, making check-in and check-out a breeze. The surrounding area was peaceful and scenic—perfect for a relaxing getaway. We would definitely recommend this place to anyone visiting the area and would love to stay again in the future!

Top Guest favourite

Guesthouse in Stephens City

5 out of 5 average rating, 17 reviews

Ventura Cottage: 360-views/HotTub/4 acres/Gym

JosetteRating, 5 stars1 month ago

Everything was top notch, pictures don't do the location justice. The ambiance is peaceful quiet fresh air beautiful views, the house is as listed and more, You get what you paid for. Leena is an amazing person very responsive and very hospitable. Don't think twice just book you will not be disappointed.

Guest favourite

Cottage in Harpers Ferry

4.98 out of 5 average rating, 64 reviews

Cozy Mountain Cottage Perfect for Friends & Family

SumeetRating, 5 stars3 weeks ago

The best Airbnb I have ever stayed in. Amazing place! Jason is a great host.

Guest favourite

Chalet in McGaheysville

4.8 out of 5 average rating, 244 reviews

Mountainside getaway in the heart of resort

ShannonRating, 5 stars1 month ago

This house was so cozy, my children loved it!! Mary & Chris was available if we needed anything. We will definitely be using their home again!!

Guest favourite

Cabin in McHenry

4.87 out of 5 average rating, 77 reviews

petfriendly-hottub-fireplace-pooltable-sunsetdeck

AdamRating, 5 stars3 weeks ago

We enjoyed our stay! The home is in a great location. We had some rain over the course of the stay which made having a roof over the hot tub very helpful. We also liked spending time in the basement with the pool table. Definitely would be interested in staying here again!

Superhost

Cabin in Luray

4.71 out of 5 average rating, 69 reviews

Cedar Breeze Cabin~River~Hiking~Mt Views~Hot Tub

Erin MairinRating, 5 stars4 months ago

We really enjoyed our stay. It was a great post Christmas trip to the region. We actually felt the photos didn't do it justice and it's a little cuter and nicer than we were expecting!

Superhost

Home in McHenry

4.89 out of 5 average rating, 107 reviews

Hot Tub EV Charger DogsOK 50"TV Fire Pit Gas Grill

BrittanyRating, 5 stars1 week ago

We had the opportunity to spend a long weekend with family members to celebrate my mother’s 70th birthday and Easter! This place was fantastic! The location was beautiful and the hosts were super responsive to any questions asked. I would highly recommend this place and I’m looking forward to going back in the near future!

Superhost

Home in Manassas

4.77 out of 5 average rating, 13 reviews

Luxury Home. Hot-tub, Fire Pit, Game Room. IAD/DC

AaronRating, 5 stars2 weeks ago

Very fun place! Perhaps somewhat new so some kinks being worked out, but the host is incredibly responsive to any requests and has invested heavily in the property - luxury fixtures, appliances, amenities. Highly recommend.

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Holiday houses in Middletown

Top-rated holiday rentals in Middletown

Holiday rentals for every style

Popular amenities for Middletown holiday rentals

Stay near Middletown's top sights

Other great holiday rentals in Middletown

Destinations to explore