Hillsboro Holiday Rentals

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Holiday Rentals in Hillsboro

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

9.6 out of 10, Exceptional, (120)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (40)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House

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

9.8 out of 10, Exceptional, (187)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (54)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (95)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Harbor View Suite Talbot County License Number STRN-25-58

10.0 out of 10, Exceptional, (31)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite Talbot County License Number STRN-25-58

Modern Flat in the Heart of St. Michaels – Walk Everywhere

10.0 out of 10, Exceptional, (49)
"We had a wonderful weekend get away. Location is perfect to take advantage of the main restaurants and shopping in St. Michael’s."
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

10.0 out of 10, Exceptional, (25)
"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests

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

9.4 out of 10, Exceptional, (3)
"We had a great stay! Ryan was a great host, and the cottage was perfect for our needs. We would certainly stay here again."
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

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

9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Charming Waterfront Stay close to St. Michaels

9.8 out of 10, Exceptional, (14)
"Great girls weekend getaway. Wonderful location and spacious accommodations. Enjoyed a relaxing stay and beautiful setting."
Charming Waterfront Stay close to St. Michaels

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (4)
"My family had a great time during our stay! The house was very clean and nice. Views were spectacular! Katie was very responsive to all of my questions. "
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (103)
"Unique and an interesting way to be close to the water."
Cass-Away Luxury Houseboat

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

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is AU$668
includes taxes & fees
6 Oct - 7 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit
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

Find out more about Hillsboro

Find out more about Hillsboro

Everything you need to know about Hillsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsboro holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hillsboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsboro holiday rentals we have selected for you start as low as AU$668 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillsboro rentals

At Expedia, we put the best Hillsboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Hillsboro?

Yes, there are holiday rentals close to the most popular sights in Hillsboro, or you can select a more secluded option if you're looking for a relaxing stay.

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

Walk to Everything House: This holiday home rental outside of Hillsboro offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Hillsboro?

Explore the area and family-friendly sights such as Easton Cycle and Sport, or get out into nature at a spot like Chesapeake Bay Environmental Center. Martinak State Park and Hog Neck Golf Course are a couple of places you'll find in the wider area.

What’s a holiday rental in Hillsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsboro. Holiday rentals provide amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.