Hillsboro Holiday Rentals

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Holiday Rentals in Hillsboro

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly

Cottage in St Michaels

9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Holiday Home in St. Michaels

9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Apartment in Saint Michaels

10.0 out of 10, Exceptional, (54)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Holiday Home in Grasonville

10.0 out of 10, Exceptional, (23)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Cottage in Saint Michaels

9.6 out of 10, Exceptional, (124)
"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!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Holiday Home in Easton

9.8 out of 10, Exceptional, (15)
"Great girls weekend getaway. Wonderful location and spacious accommodations. Enjoyed a relaxing stay and beautiful setting."
United States
Mary Y.
Charming Waterfront Stay close to St. Michaels

Houseboat in Grasonville

10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat

Cottage in St Michaels

9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cottage in Centreville

10.0 out of 10, Exceptional, (105)
"Great vacation. Relaxing and views are incredible. The host is amazing!!! "
United States
Melissa S.
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Holiday Home in Easton

10.0 out of 10, Exceptional, (95)
"Gorgeous views and surroundings"
United States
Robin P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Holiday Home in Easton

10.0 out of 10, Exceptional, (4)
"Perfect, little farmhouse! Good distance from St. Michael's, Tilghman Island, and Annapolis.We all loved staying here! Clean, fair amount of amenities, and good communication with the caretaker, Jason. "
United States
Brittany I.
The Farm House at Hunting Creek

Holiday Home in Easton

10.0 out of 10, Exceptional, (3)
"House was perfect for 5 adults and infant. Everyone had ample space but could come together. Property was spotless. Pool and dock were wonderful. Landscaping needs attention and it would have been nice to have a fire pit for the evenings. Otherwise a great place and space!!"
United States
Judi K.
Minutes from Downtown Easton and St. Michaels | Pool

Holiday Home in Easton

10.0 out of 10, Exceptional, (24)
"Second time we stayed there in a month. Came back because it is a clean, bright, tranquil setting."
United States
Scott B.
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Holiday Home in Grasonville

10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests

Holiday Home in Saint Michaels

10.0 out of 10, Exceptional, (35)
"We have stayed here multiple times and every time loved it. The house is clean, well-maintained, and ideal for a relaxing time on the water and in town. Highly recommended."
United States
Catherine K.
Downtown St. Michaels | Bikes | Kayaks | Private Pier

Holiday Home in Saint Michaels

10.0 out of 10, Exceptional, (2)
"Beautiful house, perfect for our weekend away."
United States
Ben P.
3 Bedroom St. Michaels Retreat | Walk to town

Holiday Home in Easton

9.6 out of 10, Exceptional, (21)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
United States
Peter S.
Thorneton Point Estate

Holiday Home in Centreville

9.6 out of 10, Exceptional, (34)
"Great place! Lots of room to spread our multigenerational family out and get together. Beautiful view of the Corsica River!! Close to everything but extremely private. And everyone enjoyed the game room. Definitely would stay there again."
United States
Sharon R.
Waterfront Estate w Private Pier, Game Room & Bar
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

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 favorite 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 depends 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 per night. Entering your travel dates in the search wizard you might find 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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This holiday home rental outside Hillsboro offers a garden, a BBQ 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 Hazel Miner Monument, or get out into nature at a spot like Chesapeake Bay Environmental Center. Martinak State Park and Wye Landing 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.