Photo by Michelle Gonzalez
Vacation rentals in Middletown
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Vacation rentals in Middletown
Captivating Chesapeake experience
27.22 km from city centre
Stay at this vacation home in Perryville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chestnut Point Estates and Marina and Craft Haven Marina are located nearby.
Kitchen
Washer
Chesapeake Romantic Waterfront Home with Private Pool
16.6 km from city centre
Stay at this cottage in Elkton. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Chesland Park and Brantwood Park are located nearby.
Pool
Kitchen
Chesapeake Bay House with Dock & Private Beach
17.1 km from city centre
Book a stay at this beach vacation home in Elkton. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Chesland Park and Brantwood Park are located nearby.
Kitchen
Washer
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
22.29 km from city centre
Stay at this cottage in Earleville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Turkey Point Light and Elk Neck State Park are located nearby.
Kitchen
Washer
Historic Chesapeake City Stay
12.11 km from city centre
The price is CA $165 per night
CA $165
CA $390 total
includes taxes & fees
Jun 22 - Jun 23
Stay at this cabin in Chesapeake City. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions The Pell Gardens and South Chesapeake City Historic District are located nearby.
Kitchen
Free WiFi
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
22.42 km from city centre
Book a stay at this beach apartment in Earleville. Enjoy free WiFi, a beach locale, and an in-room coffeemaker. Popular attractions Turkey Point Light and Elk Neck State Park are located nearby.
Kitchen
Free WiFi
Tip Of The Town Fresh and New 3 Bedroom Nest
25.49 km from city centre
Stay at this vacation home in North East. Enjoy free WiFi, a water park, and a garden. Popular attractions Upper Bay Museum and Milburn Stone Theater are located nearby.
Kitchen
Washer
Charming and Cozy 3-bedroom Row Home - Ideal for Students, Travelers & Families!
34.73 km from city centre
The price is CA $183 per night
CA $183
CA $448 total
includes taxes & fees
Jun 16 - Jun 17
Stay at this vacation home in Wilmington. Enjoy laundry facilities, an in-room coffeemaker, and air conditioning. Popular attractions Wilmington Riverwalk and Delaware Park Racetrack and Slots are located nearby.
Kitchen
Washer
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
24.01 km from city centre
Stay at this vacation home in Millington. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Crumpton Park and Crumpton Auction are located nearby.
Kitchen
Washer
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
19.42 km from city centre
The price is CA $203 per night
CA $203
CA $401 total
includes taxes & fees
Jun 16 - Jun 17
Stay at this vacation home in Elkton. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Elk Forest Wildlife Management Area and Harbor View Community Park are located nearby.
Kitchen
Washer
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
33.52 km from city centre
Stay at this houseboat in Havre De Grace. Enjoy laundry facilities, cable/satellite TV service, and in-room fireplaces. Popular attractions Ripken Stadium and Havre de Grace Maritime Museum are located nearby.
Kitchen
Washer
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
24.04 km from city centre
Stay at this cabin in North East. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Roachs Shore and North East Beach Area are located nearby.
Hot tub
Kitchen
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
30.85 km from city centre
Book a stay at this family-friendly vacation home in Betterton. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Betterton Beach and Betterton Historic District are located nearby.
Kitchen
Washer
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
30.53 km from city centre
Stay at this cabin in Chestertown. Enjoy a garden, laundry facilities, and patios. Popular attractions Chase Island and Crumpton Auction are located nearby.
Kitchen
Washer
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.