Holiday houses in Middletown

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Popular amenities for Middletown holiday rentals

Other great holiday rentals in Middletown

Top Guest favourite
Cabin in Fort Valley
4.99 out of 5 average rating, 72 reviews

Hidden in the Valley | Pool | Pets | Fire Pit

MichaelRating, 5 stars1 week ago
Comfortable, beautiful, peaceful place. It rained this AM and all I could hear were the sounds of nature. No traffic. Deer wonder the property, and birds are abundant; listened to 7 different types just from the front porch. The pool was a nice bonus after a hike. It’s not a far drive from DC to serenity. Great stay.
Top Guest favourite
Cabin in Star Tannery
5 out of 5 average rating, 73 reviews

Double Spur Outfitters' Brown Cabin

KatelynRating, 5 stars2 weeks ago
Beautiful place! It was squeaky clean and super comfortable. Levi was great and both proactive and responsive to any questions. We would 100% recommend this place and hope to return.
Guest favourite
Cottage in Front Royal
5 out of 5 average rating, 15 reviews

Riverfront Paradise | Hot Tub | Sauna | FirePit

ElinorRating, 5 stars2 weeks ago
Definitely coming back when the weather is warmer. TY Viktar for an amazing and peaceful weekend! Sauna and hot tub were amazing
Top Guest favourite
Cabin in Luray
5 out of 5 average rating, 7 reviews

"The Turtle" Romantic Luxury Cabin in Shenandoah

MichelleRating, 5 starstoday
We had a lovely stay at the cabin. It’s very peaceful and great for a romantic getaway. Morry was also a very responsive host. We had one issue with the building, which he promptly responded to.
Top Guest favourite
Condo in Winchester
4.99 out of 5 average rating, 78 reviews

Historic District Downtown Winchester

KelvinRating, 5 stars1 month ago
Alison's place is great if you value being walkable to Old Town. We prefer this over staying at the Wyndham Grand because of the separate room for our baby to sleep in. The kitchen is modern and fridge with a water filter is clutch. We didn't try to make any meals. Bed was clean/firm, HVAC was responsive, and lounge chair in the sitting area was comfortable. You can hear the train and street noise (especially cars w/o mufflers) at night, but I assume that's the case if you stay anywhere near Old Town.
Guest favourite
Cabin in Star Tannery
5 out of 5 average rating, 47 reviews

EagleRockCozyCabin hot tub/private/outdoor firepit

JordanRating, 5 stars2 weeks ago
A great cabin for a weekend getaway. We really appreciated all of Sabita’s recommendations for local wineries and trails. Photos and description matched the home very well. One thing to note, the cabin is off of a main road, and at times we felt like the road noise was pretty noticeable, not a huge deal, just not super tucked away/private. We would definitely stay in the future and highly recommend.
Guest favourite
Home in Front Royal
4.89 out of 5 average rating, 47 reviews

A Place of Grace - River Front

StefanieRating, 5 stars1 week ago
This place is a gem of a find - close to wineries, SNP and major stores, and downtown Front Royal, the inside of the house were the pictures, but better. The private dock, kayaks and firepit were too good to be true. We had an incredible time and anyone who visits will too. Thank you for having us Karen and Marco and hope you’ll have us back again!
Superhost
Cottage in Fort Valley
4.69 out of 5 average rating, 518 reviews

Rustic Retreat in the Valley

PedroRating, 5 stars3 weeks ago
We had a wonderful stay at this Airbnb near Luray. The views were absolutely stunning — peaceful mountains and rolling hills all around. We visited the Luray Caverns, which were truly breathtaking, and made a stop in Woodstock for some amazing BBQ. The house was cozy, clean, and perfect for relaxing with friends. We spent our evenings laughing, playing games, and enjoying the quiet. It was the perfect spot to unwind and make lasting memories.

Destinations to explore

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  2. United States
  3. Virginia
  4. Frederick County
  5. Middletown