Hillsboro Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Hillsboro hotels

Cottages in Hillsboro

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and St. Michaels Marina.

Pool

Kitchen

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Centreville MD

With a stay at this cottage in Centreville, you'll be on the waterfront, and 6.5 mi (10.5 km) from Queenstown Premium Outlets and 6.9 mi (11.1 km) from Queenstown Harbor Golf Links.

Kitchen

Washer

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Cozy, unique, historic registered cottage on the Corsica River!

Centreville MD

With a stay at this cottage in Centreville, you'll be within a 15-minute drive of Earle Landing and Queenstown Premium Outlets.

Kitchen

Washer

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Trappe MD

With a stay at this cottage in Trappe, you'll be within a 10-minute drive of The Third Haven Friends Meeting House and Easton Cycle and Sport.

Pool

Kitchen

Cottage downtown on a quiet street

St. Michaels MD

A stay at this cottage places you in the heart of St. Michaels, within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.

Kitchen

Washer

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

Wye Mills MD

With a stay at this cottage in Queenstown, you'll be a short 4-minute walk from Wye Oak State Park and within 3 minutes by car from Rufus M and Loraine Hall Todd Performing Arts Center.

Kitchen

Washer

Grasonville Home w/ Private Pool on the Water

Grasonville MD

When you stay at this cottage in Grasonville, you'll be within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.

Pool

Kitchen

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

Denton MD

With a stay at this cottage in Denton, you'll be within a 5-minute drive of Williston Lake and Caroline County 4-H Club and Youth Park.

Pool

Kitchen

4BR House Winchester Creek Estate

Grasonville MD

When you stay at this cottage in Grasonville, you'll be within a 10-minute drive of Queenstown Premium Outlets and Chesapeake Exploration Center.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Hillsboro

View all properties

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.