
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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Other great holiday rentals in Middletown
Top Guest favourite

Cabin in Fort Valley
4.99 out of 5 average rating, 72 reviewsHidden 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 reviewsDouble 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 reviewsRiverfront 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 reviewsHistoric 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 reviewsEagleRockCozyCabin 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 reviewsA 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 reviewsRustic 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.
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- Massanutten Resort
- Luray Caverns
- Stone Tower Winery
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Early Mountain Winery
- Bryce Resort
- Prince Michel Winery
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Creighton Farms
- Twin Lakes Golf Course
- Berkeley Springs State Park
- Bowling Green Country Club
- Reston National Golf Course
- JayDee's Family Fun Center
- River Creek Club
- Warden Lake
- Herndon Centennial Golf Course
- Dinosaur Land
- The Golf Club at Lansdowne
- Car and Carriage Caravan Museum