Vacation rentals in Middletown
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Top-rated accommodation in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.
Cottage in Winchester
4.98 out of 5 average rating, 296 reviewsUber SXY Private Country Escape! Hot Tub & Views~
Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...
24 Feb – 3 Mar
Home in Strasburg
4.99 out of 5 average rating, 169 reviewsHistoric 250 Year Old Strasburg Home
Holliday & King is a great option for families or a group of friends who want to get away and enjoy small town life, explore Shenandoah National Park and the George Washington National Forest. Both are 10 miles away. Located in the center of Strasburg's historic district, it is 1 to 2 blocks to small restaurants, a brewery and shopping. The house itself is part of the Town's history, built in 1761. Enjoy large rooms, high ceilings and a lovely porch where you can watch activity in the town.
1 – 8 May
Apartment in Winchester
5.0 out of 5 average rating, 134 reviewsOld Town Loft In Highly Desirable Area Downtown
Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.
6 – 13 Aug
Accommodation for every style
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Popular amenities for Middletown accommodation
Other great accommodation in Middletown
Home in Winchester
4.97 out of 5 average rating, 210 reviewsCity Charmer minutes from Old Town
20 – 27 Aug
Cabin in Lost City
4.97 out of 5 average rating, 245 reviewsHigh View Hideaway - A Cozy Lost River Cabin
17 – 24 June
Place to stay in Bentonville
4.98 out of 5 average rating, 384 reviewsJohn Pope Cabin Browntown Va. We now have Starlink
13 – 20 July
Apartment in Winchester
4.98 out of 5 average rating, 214 reviewsDowntowner
3 – 10 Sept
Home in Middletown
4.86 out of 5 average rating, 29 reviewsMountain View Moto Retreat
29 Apr – 6 May
Home in Middletown
4.79 out of 5 average rating, 89 reviewsThe Blue House
17 – 24 Nov
Home in Middletown
4.94 out of 5 average rating, 34 reviewsCozy Retreat in Reliance with beautiful views
28 Dec – 4 Jan
Cottage in Winchester
4.89 out of 5 average rating, 95 reviewsLockley Cottage at Historic Perry Farm
7 – 14 Sept
Apartment in Winchester
4.96 out of 5 average rating, 45 reviewsNewly repurposed Historic Home in Winchester VA!
14 – 21 July
Home in Strasburg
5.0 out of 5 average rating, 10 reviewsShenandoah Valley Mountain House Entire Home
23 – 30 Oct
Guesthouse in Middletown
4.86 out of 5 average rating, 29 reviewsRiverfront Oasis with Mountain Views, Near Town
3 – 10 Apr
Home in Front Royal
4.96 out of 5 average rating, 92 reviewsCozy house in Shenandoah N.P. City of Front Royal
5 – 12 May
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