Vacation rentals in Middletown

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Popular amenities for Middletown vacation rentals

Other great vacation rentals in Middletown

Top guest favorite
An inground pool is surrounded by a wooden fence, with comfortable lounge chairs positioned nearby. The setting includes a grassy area leading to the pool, bordered by trees that provide a natural backdrop. A small shed is visible in the background.
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 favorite
A tranquil stream flows over a rocky bed, with clear water cascading over smooth stones. Sunlight reflects on the surface, revealing a mix of light and dark rocks beneath. Surrounding trees and earthy tones create a natural setting that invites relaxation.
Cabin in Star Tannery
5 out of 5 average rating, 73 reviews

Double Spur Outfitters' Brown Cabin

KatelynRating, 5 stars1 week 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 favorite
An outdoor deck overlooking the serene river features comfortable seating arranged around a fire pit, illuminated by string lights. The warm glow reflects off the water, creating a peaceful atmosphere, while lush greenery lines the riverbank under the colorful evening sky.
Cottage in Front Royal
5 out of 5 average rating, 15 reviews

Riverfront Paradise | Hot Tub | Sauna | FirePit

ElinorRating, 5 stars1 week 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 favorite
A private deck showcases a built-in hot tub with seating nearby. The outdoor lounge area features a cushioned sofa and a rectangular coffee table, inviting relaxation and enjoyment of the surrounding green landscape. Large glass doors provide seamless access to the interior.
Cabin in Luray
5 out of 5 average rating, 6 reviews

"The Turtle" Romantic Luxury Cabin in Shenandoah

CatherineRating, 5 stars1 week ago
I enjoyed my time at Morry’s place. He was very professional and answered any questions I had in a timely manner. His beautiful home was peaceful. It was just as described, and my dog enjoyed himself. I look forward to booking again in the future.
Top guest favorite
A vibrant street in Old Town Winchester features historic buildings with colorful façades, outdoor seating marked by umbrellas, and a towering Christmas tree adorned with decorations. A clear blue sky complements the scene, while the atmosphere suggests a lively pedestrian area filled with shops and dining options.
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 favorite
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 favorite
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.

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  4. Frederick County
  5. Middletown