Hillsboro Vacation Rentals

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Vacation Rentals in Hillsboro

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

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

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (19)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is CA $615
CA $1,071 total
includes taxes & fees
Aug 2 - Aug 3
Waterfront Sunset Bayview: sleeps 6

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"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

Studio in Downtown – Walk to Everything!

10.0 out of 10, Exceptional, (20)
"This was the perfect spot for a long weekend. Excellent location and the unit itself was more than we expected. "
Studio in Downtown – Walk to Everything!

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (32)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

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

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is CA $270
CA $610 total
includes taxes & fees
Jul 29 - Jul 30
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

10.0 out of 10, Exceptional, (16)
"We loved this home. The location is excellent--close to areas like Easton and St Michael's, but out of the way and secluded. We loved sitting on the lawn by the Dixon Creek and watching the sunset. House is well stocked, and wifi is strong--supported 3 people who had to work. Highly recommend this beautiful home."
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (102)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $343
CA $574 total
includes taxes & fees
Jul 29 - Jul 30
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (5)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

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

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (9)
"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

Walk to Everything House

10.0 out of 10, Exceptional, (79)
"Clean and nice place to stay"
Walk to Everything House

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (52)
"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

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is CA $371
CA $1,236 total
includes taxes & fees
Aug 3 - Aug 4
Gorgeous Creek Side Ranch-Style Estate With Dock

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (9)
"The property is a great place to get away and enjoy some time with family. We enjoyed swimming in the pool. Fishing was fun as well catfish for days. Nice sunsets by the fire and just overall a great time with the family. "
Riverfront Denton Estate on 7 Acres w/ 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

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: This vacation home rental near Hillsboro 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 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 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.