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Hotels in Middletown

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Choose from 620 Middletown Hotel Deals

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St Middletown VA
  • 14 min walk from Belle Grove Plantation
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Cedar ...
9.2/10 Wonderful! (426 reviews)
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful

Reviewed on Mar 16, 2026

Wayside Inn
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
  • 23 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
Clean room, friendly staff, good location. Only cons were hallway carpet is rippled and no free breakfast

Reviewed on Mar 27, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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
  • 24 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,271 reviews)
Very nice would stay there again

Reviewed on Mar 26, 2026

La Quinta Inn & Suites 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
  • 28 min drive from Belle Grove Plantation
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,000 reviews)
Location of hotel is great for walking to restaurants and shops.

Reviewed on Mar 18, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
  • 23 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,001 reviews)
I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature

Reviewed on Mar 26, 2026

Sleep Inn & Suites Winchester near University
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
  • 33 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,457 reviews)
Room was clean. Very basic room. Breakfast was adequate.

Reviewed on Mar 26, 2026

Microtel Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
  • 17 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,091 reviews)
Overall a pleasant stay!

Reviewed on Mar 27, 2026

Comfort Inn & Suites Winchester
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 out of 5
1011 Motel Dr Woodstock VA
  • 27 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,000 reviews)
It was outdated in general. There were a couple large stains on the carpet. It needs to be updated. The gym was very small.

Reviewed on Mar 15, 2026

Comfort Inn Woodstock Shenandoah
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive Winchester VA
  • 29 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (948 reviews)
Staff is friendly and the rooms are clean. Location is convenient to everything in Winchester

Reviewed on Mar 22, 2026

Courtyard by Marriott Winchester
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET Winchester VA
  • 34 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (826 reviews)
Great room! Nice bed! Very clean. Lovely shower and bath. I will stay again.

Reviewed on Mar 22, 2026

SpringHill Suites by Marriott Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive Winchester VA
  • 25 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,000 reviews)
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel

Reviewed on Mar 15, 2026

Hampton Inn Winchester-University/Mall Area
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

3 out of 5
250 Front Royal Pike Winchester VA
  • 23 min drive from Belle Grove Plantation
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (829 reviews)
Right off 81 with several restaurants nearby. Spacious rooms

Reviewed on Mar 23, 2026

Fairfield Inn & Suites by Marriott Winchester
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.

Find cheap hotels in Middletown

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