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.

Guest favourite

Cottage in Winchester

4.98 out of 5 average rating, 296 reviews

Uber 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

$2,755 AUD total
Guest favourite

Home in Strasburg

4.99 out of 5 average rating, 169 reviews

Historic 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

$2,583 AUD total
Guest favourite

Apartment in Winchester

5.0 out of 5 average rating, 134 reviews

Old 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

$1,925 AUD total

Popular amenities for Middletown accommodation

Other great accommodation in Middletown

Guest favourite

Home in Winchester

4.97 out of 5 average rating, 210 reviews

City Charmer minutes from Old Town

20 – 27 Aug

$1,569 AUD total
Guest favourite

Cabin in Lost City

4.97 out of 5 average rating, 245 reviews

High View Hideaway - A Cozy Lost River Cabin

17 – 24 June

$1,325 AUD total
Guest favourite

Place to stay in Bentonville

4.98 out of 5 average rating, 384 reviews

John Pope Cabin Browntown Va. We now have Starlink

13 – 20 July

$2,029 AUD total
Guest favourite

Apartment in Winchester

4.98 out of 5 average rating, 214 reviews

Downtowner

3 – 10 Sept

$1,415 AUD total
Guest favourite

Home in Middletown

4.86 out of 5 average rating, 29 reviews

Mountain View Moto Retreat

29 Apr – 6 May

$1,158 AUD total
Superhost

Home in Middletown

4.79 out of 5 average rating, 89 reviews

The Blue House

17 – 24 Nov

$1,789 AUD total
Guest favourite

Home in Middletown

4.94 out of 5 average rating, 34 reviews

Cozy Retreat in Reliance with beautiful views

28 Dec – 4 Jan

$2,275 AUD total
Guest favourite

Cottage in Winchester

4.89 out of 5 average rating, 95 reviews

Lockley Cottage at Historic Perry Farm

7 – 14 Sept

$1,042 AUD total
Guest favourite

Apartment in Winchester

4.96 out of 5 average rating, 45 reviews

Newly repurposed Historic Home in Winchester VA!

14 – 21 July

$1,285 AUD total
Guest favourite

Home in Strasburg

5.0 out of 5 average rating, 10 reviews

Shenandoah Valley Mountain House Entire Home

23 – 30 Oct

$1,890 AUD total
Superhost

Guesthouse in Middletown

4.86 out of 5 average rating, 29 reviews

Riverfront Oasis with Mountain Views, Near Town

3 – 10 Apr

$2,307 AUD total
Guest favourite

Home in Front Royal

4.96 out of 5 average rating, 92 reviews

Cozy house in Shenandoah N.P. City of Front Royal

5 – 12 May

$1,647 AUD total

Destinations to explore

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