Hillsboro Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Hillsboro vacation rentals

Property grounds
Turnbridge Manor

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥56,138
￥95,045 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Turnbridge Manor
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is ￥30,736
￥69,442 total
includes taxes & fees
Jan 6 - Jan 7, 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is ￥38,985
￥65,292 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
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Top Hillsboro Hotel Reviews

Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

10/10 Excellent
"Great place. Incredible views. Unique experience. Stellar location. Clean and comfortable furnishing. Walking distance to great restaurants and bars on the water. "
Mike W. 3-night trip
Posted 2 days ago
Cass-N-Reel Luxury Houseboat

Find out more about Hillsboro

Search for holiday rentals in Hillsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsboro using one of the methods below:

  • View our selection of featured holiday rentals in Hillsboro
  • Use the map to find apartments and other holiday homes in the Hillsboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsboro while they last

Look no further and take a look at our great range of rental properties in Hillsboro!

Frequently asked questions

Can I find vacation rentals in Hillsboro?

Yes, you can find vacation rentals close to well known local attractions in Hillsboro, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Hillsboro has to offer?

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks: Located near Hillsboro, this vacation home rental is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Hillsboro?

Explore the area and family-friendly sights such as Hazel Miner Monument, or get out into nature at a spot like Chesapeake Bay Environmental Center. Wye Landing and Pickering Creek Audubon Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Hillsboro like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Hillsboro. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.