Title: Hillsboro Vacation Rentals : Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Hillsboro](https://expedia.ca/Hillsboro-Hotels.d553248634999258593.Travel-Guide-Hotels)[Hillsboro Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsboro.d553248634999258593.Car-Rental-Guide)[Hillsboro Vacation Packages](https://expedia.ca/Hillsboro.d553248634999258593.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Hillsboro vacation rentals

![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

Exceptional

(12 reviews)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe C.

CA $340

CA $574 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/a1d87464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/dd899134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/w1170h1577x0y0-bbbe5be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/1e473e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Turnbridge Manor

[](https://www.expedia.ca/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information)

Denton

9.8/10

Exceptional

(12 reviews)

"Really nice place and you can walk to everything.Will stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Glenn S.

CA $490

CA $842 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&regionId=553248634999258593&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Hillsboro%2C+Maryland%2C+United+States+of+America&regionId=553248634999258593&latLong=38.91678%2C-75.938827&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Hillsboro%2C+Maryland%2C+United+States+of+America&regionId=553248634999258593&latLong=38.91678%2C-75.938827&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Hillsboro%2C+Maryland%2C+United+States+of+America&regionId=553248634999258593&latLong=38.91678%2C-75.938827&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Hillsboro%2C+Maryland%2C+United+States+of+America&regionId=553248634999258593&latLong=38.91678%2C-75.938827&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME)

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## Top Hillsboro Hotel Reviews

![Fairfield Inn & Suites by Marriott Easton](https://images.trvl-media.com/lodging/13000000/12010000/12009900/12009838/6e42f8e0_y.jpg)

### Fairfield Inn & Suites by Marriott Easton

10/10 Excellent

"Friendly staff, clean room. Will stay again. "

[](https://expedia.ca/Easton-Hotels-Fairfield-Inn-Suites-By-Marriott-Easton.h12009838.Hotel-Information)

![Best Western Plus Easton Inn & Suites](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b_y.jpg)

### Best Western Plus Easton Inn & Suites

10/10 Excellent

"Mini solo sewing retreat. Two queens-- one for sleep one for laying out my project. Lots of surfaces to set up cutting and ironing stations. Breakfast, fridge, microwave. Quilt and Michael's shop in town. Just what I needed to get away. "

[](https://expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information)

![Hampton Inn Easton](https://images.trvl-media.com/lodging/2000000/1440000/1432500/1432437/w1504h992x0y8-f18eeee9_y.jpg)

### Hampton Inn Easton

10/10 Excellent

"Everything was top notch."

[](https://expedia.ca/Easton-Hotels-Hampton-Inn-Easton.h1432437.Hotel-Information)

![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg)

### Best Western Kent Narrows Inn

10/10 Excellent

"The breakfast was good. The staff was friendly. It was quiet. And the mattress was amazing."

[](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg)

### Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Amazing location and staff!"

[](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Holiday Inn Express Easton by IHG](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/540d96d0_y.jpg)

### Holiday Inn Express Easton by IHG

10/10 Excellent

"Goog"

[](https://expedia.ca/Easton-Hotels-Holiday-Inn-Express-Easton.h2264.Hotel-Information)

![Holiday Inn Express Annapolis East-Kent Island by IHG](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934_y.jpg)

### Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Clean room, I enjoy staying here every time I'm in the area"

[](https://expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_y.jpg)

### Hilton Garden Inn Kent Island Marina

10/10 Excellent

"The room was very nice; the only problem was that the bathroom door was hard to navigate around. The hotel is in great shape, and the staff were very friendly and helpful. "

[](https://expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

![Best Western Denton Inn](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101833/9475aafe_y.jpg)

### Best Western Denton Inn

10/10 Excellent

"Clean room good staff "

[](https://expedia.ca/Denton-Hotels-Best-Western-Denton-Inn.h1101833.Hotel-Information)

## Find out more about Hillsboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillsboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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## Frequently asked questions

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

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