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Search Middletown Hotels, Winchester

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Top 10 Hotels in Middletown

See all available properties in Middletown
Fairfield Inn & Suites Strasburg Shenandoah Valley
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
Free cancellationReserve now, pay when you stay
£74
per night
18 Dec-19 Dec
4.4/5Wonderful! (664 reviews)

"I loved that the breakfast had vegetarian options - veggie sausage and soy milk. Not many hotels offer this."…"

Reviewed on 11 Nov 2019

Fairfield Inn & Suites Strasburg Shenandoah Valley
Hampton Inn & Suites Woodstock, VA
Hampton Inn & Suites Woodstock, VA
2.5 out of 5
1150 Motel Dr, Woodstock, VA
Free cancellationReserve now, pay when you stay
£69
per night
31 Dec-1 Jan
4.5/5Wonderful! (986 reviews)

"Night staff very kind morning ladies at desk not so much"…"

Reviewed on 9 Dec 2019

Hampton Inn & Suites Woodstock, VA
Wingate by Wyndham Winchester
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free cancellationReserve now, pay when you stay
£67
per night
10 Jan-11 Jan
4.4/5Excellent! (1,118 reviews)

"Easy location. Great room size. Lot’s of things to do in the area. Great location do. Great stay."…"

Reviewed on 27 Nov 2019

Wingate by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free cancellationReserve now, pay when you stay
£78
per night
29 Dec-30 Dec
4.7/5Exceptional! (1,105 reviews)

"This is a very elegant, beautifully maintained historic hotel. Our room was pretty and generously sized with a very comfortable bed. The linens were crisp and absolutely spotless. Overall cleanliness of the room and the hotel is very high. We enjoyed our visit and would stay again at this hotel. ..."…"

Reviewed on 6 Dec 2019

The George Washington Hotel, A Wyndham Grand Hotel
Ramada by Wyndham Strasburg
Ramada by Wyndham Strasburg
2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Free cancellationReserve now, pay when you stay
£48
per night
25 Dec-26 Dec
3.7/5Good! (915 reviews)

"Breakfast only ser ed until 9:30. Coffee pits and waffle machine were EMPTY!"…"

Reviewed on 26 Nov 2019

Ramada by Wyndham Strasburg
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
£46
per night
18 Dec-19 Dec
3.5/5Good! (1,658 reviews)

"Staff was great. We had to change rooms because the first room smelled of cigarettes. The room was clean but hallways were not."…"

Reviewed on 11 Dec 2019

Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free cancellationReserve now, pay when you stay
£62
per night
22 Dec-23 Dec
4.3/5Excellent! (1,661 reviews)

"Very nice hotel and extremely friendly staff. We enjoyed our stay at this hotel."…"

Reviewed on 8 Dec 2019

La Quinta Inn & Suites by Wyndham Winchester
Clarion Inn & Conference Center
Clarion Inn & Conference Center
2.5 out of 5
711 Millwood Ave, Winchester, VA
Free cancellationReserve now, pay when you stay
£43
per night
25 Dec-26 Dec
3.8/5Good! (849 reviews)

"We liked the fact the restaurant was attached and we didnt have to walk far."…"

Reviewed on 10 Dec 2019

Clarion Inn & Conference Center
Motel 6 Winchester, VA
Motel 6 Winchester, VA
2 out of 5
2951 Valley Avenue, Winchester, VA
Free cancellation
£46
per night
3 Jan-4 Jan
4/5Very Good! (743 reviews)

"I was impressed with the motel, very good value. The bed was comfortable and the room was spacious."…"

Reviewed on 2 Dec 2019

Motel 6 Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free cancellationReserve now, pay when you stay
£74
per night
15 Dec-16 Dec
4.5/5Wonderful! (1,712 reviews)

"Tell was in a good location near Highway 81, making it convenient to get off and on my travel. Yes, the breakfast is free, but the coffee isn’t the best."…"

Reviewed on 5 Dec 2019

Country Inn & Suites by Radisson, Winchester, VA
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Visiting Middletown

Visitors to Middletown are sure to enjoy the bars and restaurants. Tourists can also enjoy the city's entertainment choices, churches and theatres.

  • You'll find 77 Expedia hotels and other accommodation options in the larger area of Winchester
  • The closest major airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), 30.3 mi (48.7 km) from the city centre
  • The next closest is in Washington, DC (IAD-Washington Dulles Intl.), 44.9 mi (72.3 km) away

Sightseeing and Staying in Middletown

The city is notable for its historic sites and landmarks like Belle Grove Plantation and Cedar Creek Battlefield Foundation. A couple of additional sights to add to your agenda are Wayside Theater and Jackson's Chase Golf Course.

Here's a top place to stay based on our user reviews:

  • Wayside Inn - This 3.5-star inn features free breakfast, a restaurant and free WiFi. It's a favourite with Expedia travellers for its helpful staff and clean, comfortable rooms.

Dressing for Middletown

  • Between January and March, you can expect the daytime average to be around 16°C and the night-time average to be -5°C
  • From April to June, temperatures average about 30°C during the day and 3°C at night
  • July to September averages 31°C during the day and 10°C at night
  • Between October and December, the average temperature is 23°C during the day and -5°C at night
  • Middletown gets about 1040 millimetres of rain per year
  • Hottest months are usually July and August with an average temperature of 30°C, while the coldest months are January and December with an average of -4°C

Frequently asked questions

Middletown Hotel Reviews

  • Travelodge by Wyndham Winchester
    Expedia Verified Review…
    4 out of 5
    Staff was great. We had to change rooms because the first room smelled of cigarettes. The room was clean but hallways were not.…
    A verified traveller stayed at Travelodge by Wyndham Winchester
    Posted 20 hours ago
    Travelodge by Wyndham Winchester
  • Hotel Strasburg
    Expedia Verified Review…
    5 out of 5
    Everything in a hotel was 1800's Decor, Including the building!! Just loved it all!…
    A verified traveller from North Babylon, N.Y. stayed at Hotel Strasburg
    Posted 8 days ago
    Hotel Strasburg
  • Hampton Inn Winchester-University/Mall Area
    Expedia Verified Review…
    5 out of 5
    Perfect location, right off 81. Good breakfast! Staff was a little loud early in the morning (we were on the 4th floor), and it was Sunday morning.…
    A verified traveller from Boone, NC stayed at Hampton Inn Winchester-University/Mall Area
    Posted 9 days ago
    Hampton Inn Winchester-University/Mall Area
  • Blue Ridge Motel
    Expedia Verified Review…
    4 out of 5
    The motel was convenient for my travel needs and the price was hard to beat. The room was especially small but clean and the beds were comfortable. …
    A verified traveller stayed at Blue Ridge Motel
    Posted 2 months ago
    Blue Ridge Motel
  • Red Roof Inn Winchester
    Expedia Verified Review…
    4 out of 5
    I love staying here but the bathroom wasnt as clean as usual.…
    A verified traveller from Hancock ny stayed at Red Roof Inn Winchester
    Posted 2 months ago
    Red Roof Inn Winchester

More trip options

See a list of all hotels in Middletown

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