Name: La Quinta Inn & Suites by Wyndham Winchester
Price range: $119 total
Rating: 9.2

Wayside Inn

7783 Main St Middletown VA

$134 nightly

$147 total

Apr 3 - Apr 4

Total with taxes and fees

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

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

$91 nightly

$99 total

Apr 5 - Apr 6

Total with taxes and fees

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! (1,000 reviews)

Breakfast was excellent and all the staff were very friendly.

Reviewed on Mar 30, 2026

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

$110 nightly

$119 total

Apr 5 - Apr 6

Total with taxes and fees

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! (2,268 reviews)

The breakfast was subpar. Food was sparse Waffle maker didn't consistently work.

Reviewed on Apr 1, 2026

See all 633 properties in Middletown

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.

Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!

Rileyville VA

Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ...

9.8/10 Exceptional! (308 reviews)

The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly.

Reviewed on Feb 18, 2026

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Front Royal VA

Stay at this cabin in Front Royal. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ...

9.6/10 Exceptional! (343 reviews)

The space was cozy and nice. The view of the river was absolutely breathtaking from the back porch! Quiet and relaxing.

Reviewed on Mar 23, 2026

Secluded River Cabin Getaway (Masten Cabin)

Strasburg VA

Stay at this vacation home in Strasburg. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Secret Passage Ranch and Strasburg Museum are located ...

9.8/10 Exceptional! (182 reviews)

Very nice pet friendly cabin outside of town, yet still close enough to everything. Cabin had everything we needed for a few day getaway. Was very clean and as described. Check in process and instructions were super easy. We enjoyed our stay and 100% would stay again if we come back to the area.

Reviewed on Mar 16, 2026

See all properties in Middletown

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.

Popular places to visit

Belle Grove Plantation

Learn about the local history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.

Cedar Creek and Belle Grove National Historical Park

Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.