Middletown, MD

Travel Guide

Photo by Doug Kerr
Photo by Doug Kerr
Photo by Ann Sair
Photo by Ann Sair
Photo by Willow Rock
Photo by Willow Rock
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Middletown
Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and patios. Popular attractions Maryland National Golf Club and Orchid Cellar Winery are located ...
10/10 Exceptional! (91 reviews)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back!"

Reviewed on 10 January 2025

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Countryside Cabin with Mountain Views near Surreybrooke Gardens
Serene Log Cabin Nestled Among the Battlefields
Serene Log Cabin Nestled Among the Battlefields
Middletown
Stay at this cabin in Middletown. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Orchid Cellar Winery and Washington Monument State ...
8/10 Very Good! (26 reviews)
Serene log cabin.
"Our overall experience was nice and relaxing place to be. However, during the cold months. The second floor was warm enough to sleep, but the first floor was very cold, especially when it gets down to 19 at night when there’s no heat because all the heat travels to the second floor/loft. There was ..."

Reviewed on 2 March 2025

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Serene Log Cabin Nestled Among the Battlefields
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
The price is AED 349 per night from Mar 26 to Mar 27
AED 349
AED 783 total
includes taxes & fees
26 Mar - 27 Mar
Stay at this cabin in Middletown. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery ...
9.6/10 Exceptional! (89 reviews)
Very nice stay!
"The cabin was cozy, quiet, and we felt right at home! It had a cute rustic vibe and was very peaceful, despite being in a neighborhood. Easy access to Main Street Middletown with some great restaurants and sights. The cabin had everything we needed for our stay, including kitchen supplies, extra ..."

Reviewed on 17 March 2025

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
See all 737 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.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Middletown
Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and patios. Popular attractions Maryland National Golf Club and Orchid Cellar Winery are located ...
10/10 Exceptional! (91 reviews)
"Absolutely beautiful cozy and idyllic and Cassandra was extremely responsive! Also very close to amazing hiking at Gambrills park. Ill be back!"

Reviewed on 10 January 2025

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
Stay at this cabin in Middletown. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery ...
9.6/10 Exceptional! (89 reviews)
Very nice stay!
"The cabin was cozy, quiet, and we felt right at home! It had a cute rustic vibe and was very peaceful, despite being in a neighborhood. Easy access to Main Street Middletown with some great restaurants and sights. The cabin had everything we needed for our stay, including kitchen supplies, extra ..."

Reviewed on 17 March 2025

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Charming "Cream of the Crop" Cape ~❤️of Middletown
Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
Stay at this vacation home in Middletown. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Orchid Cellar Winery and ...
9.8/10 Exceptional! (121 reviews)
Nice weekend
"Visited nice restaurants, brew pubs, antique shops. House was perfect for us. Very clean and well equipped."

Reviewed on 16 March 2025

Charming "Cream of the Crop" Cape ~❤️of Middletown
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

Maryland National Golf Club

Enjoy a round of golf in Middletown at Maryland National Golf Club. Discover the coffeehouses and its festivals while you're in the area.

Maryland National Golf Club

Orchid Cellar Winery

You can enjoy a tasting or tour at Orchid Cellar Winery during your travels to Middletown. Discover the area's festivals, or seek out its golf courses.

Orchid Cellar Winery

Willow Oaks Craft Cider and Wine

You can enjoy a tasting or tour at Willow Oaks Craft Cider and Wine during your travels to Middletown. Amble around the area's riverfront or experience its entertainment venues.

Willow Oaks Craft Cider and Wine