Title: Henderson Vacation Rentals from CA $220: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000440669&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=3000440669&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=3000440669&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=3000440669&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Henderson vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/5cb9165d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Studio Apartment in Historic Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

Chestertown

9.6/10

Exceptional

(108 reviews)

"Every thing was great"

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

lesia k.

CA $137

CA $220 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/fa7600d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/4580f93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/5e712dd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/26dc0ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

[](https://www.expedia.ca/Frederica-Hotels-Totally-Remodeled-Cozy-Apartment-25-Miles-To-Delaware-Turf.h101532690.Hotel-Information)

Frederica

10/10

Exceptional

(19 reviews)

"Super cute and clean place, the host was very responsive to my questions. "

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

Gosha R.

CA $90

CA $255 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Frederica-Hotels-Totally-Remodeled-Cozy-Apartment-25-Miles-To-Delaware-Turf.h101532690.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w423h683x305y0-6862acf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guest Suite for up to 2 in a Victorian on the Chester River

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

Millington

9.6/10

Exceptional

(20 reviews)

"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."

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

Cynthia C.

CA $94

CA $173 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information)

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

![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.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 $346

CA $585 total

includes taxes & fees

Apr 13 - Apr 14

[](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)

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

![Dining](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/164dc219.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)

### 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 $499

CA $856 total

includes taxes & fees

Apr 13 - Apr 14

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

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/1afdcb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/76b495fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Modern house with a full kitchen and parking 

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

Smyrna

9.2/10

Wonderful

(10 reviews)

"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "

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

Laurie S.

CA $176

CA $406 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b4e88275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/b0be7e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/ee75c514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/105000000/104010000/104005300/104005223/daf32ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

[](https://www.expedia.ca/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

Rock Hall

10/10

Exceptional

(18 reviews)

"Close to Main Street. Very nice and spacious accommodations."

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

Michael D.

CA $163

CA $397 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Rock-Hall-Hotels-Walk-To-Everything-Rock-Hall-From-This-1st-Floor-Apartment-Sleeps-4.h104005223.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/4cfce214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/ce9b7709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bayside Cottage steps from Rock Hall Harbor

[](https://www.expedia.ca/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

Rock Hall

10/10

Exceptional

(2 reviews)

"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"

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

Dorothy R.

CA $243

CA $501 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/128000000/127890000/127885900/127885895/69361b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/128000000/127890000/127885900/127885895/e97c97d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/128000000/127890000/127885900/127885895/f30ca588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/128000000/127890000/127885900/127885895/366a0955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Bay Retreat w/ Delaware Bay views / 2 min walk to the beach / Sleeps 5

[](https://www.expedia.ca/Dover-Hotels-Tiny-Bay-House-W-Loft-2-Min-Walk-To-The-Beach-Family-Friendly-Sleeps-5.h127885895.Hotel-Information)

Dover

CA $316

CA $524 total

includes taxes & fees

Apr 26 - Apr 27

[](https://www.expedia.ca/Dover-Hotels-Tiny-Bay-House-W-Loft-2-Min-Walk-To-The-Beach-Family-Friendly-Sleeps-5.h127885895.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/b3e8d5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/242b2346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/4d8cbe20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/a373d2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### JVA LUXURY HOUSING

[](https://www.expedia.ca/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.Hotel-Information)

Smyrna

10/10

Exceptional

(1 review)

"The house was clean and wonderful. I highly recommend!"

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

Daryl C.

CA $554

CA $814 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.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=2026-04-22&endDate=2026-04-23&regionId=3000440669&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Henderson%2C+Maryland%2C+United+States+of+America&regionId=3000440669&latLong=39.074382%2C-75.765898&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=COTTAGE)

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## Top Henderson Hotel Reviews

![Sleep Inn & Suites Dover University Area](https://images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/e37ca31f_y.jpg)

### Sleep Inn & Suites Dover University Area

10/10 Excellent

"Very friendly people, quick check in. Huge room by todays standards. Standard breakfast for a sleep inn, which is fine for us. Good coffee. It was only one night but would stay there again next timecwe visit family."

[](https://expedia.ca/Dover-Hotels-Sleep-Inn-And-Suites.h2115064.Hotel-Information)

![Springhill Suites By Marriott Frederica](https://images.trvl-media.com/lodging/96000000/95070000/95062700/95062671/9f69013a_y.jpg)

### Springhill Suites By Marriott Frederica

10/10 Excellent

"This is a new hotel in mint condition. The room was spacious and comfortable. No issues with parking in a lighted area close to the building. Staff were friendly and welcoming. Only business nearby was a liquor store. Breakfast was a little disappointing, just typical motel free breakfast fare."

[](https://expedia.ca/Frederica-Hotels-Springhill-Suites-By-Marriott-Frederica.h95062671.Hotel-Information)

![Quality Inn & Suites Harrington - Milford](https://images.trvl-media.com/lodging/1000000/700000/694400/694352/1d5d612d_y.jpg)

### Quality Inn & Suites Harrington - Milford

8/10 Good

"The room was clean and the staff was very friendly and helpful. I needed a place to stay for a tournament at the DE Turf facility and this was one of the most convenient locations. My only reason for the lack of 5 stars is just the normal wear and tear on a hotel. It is one hundred percent one of the best values in the area. I would definitely book and stay here for the next tournament I have to go to. "

[](https://expedia.ca/Dover-Hotels-Quality-Inn-And-Suites.h694352.Hotel-Information)

![Red Roof Inn & Suites Dover Downtown](https://images.trvl-media.com/lodging/1000000/890000/888000/887960/7eedec33_y.jpg)

### Red Roof Inn & Suites Dover Downtown

10/10 Excellent

"Clean "

[](https://expedia.ca/Dover-Hotels-Red-Roof-Inn-Suites-Dover-Downtown.h887960.Hotel-Information)

![Fairfield Inn & Suites by Marriott Dover](https://images.trvl-media.com/lodging/1000000/870000/861200/861129/0f2f267f_y.jpg)

### Fairfield Inn & Suites by Marriott Dover

10/10 Excellent

"I would stay here again "

[](https://expedia.ca/Dover-Hotels-Fairfield-Inn-Suites-By-Marriott-Dover.h861129.Hotel-Information)

![Hilton Garden Inn Dover](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/852282e7_y.jpg)

### Hilton Garden Inn Dover

8/10 Good

"The was freezing cold! The toilets are too short"

[](https://expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information)

![Bally's Dover Casino Resort](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/f76eefb5_y.jpg)

### Bally's Dover Casino Resort

6/10 Okay

"internet did not work. neighbors were loud all night."

[](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information)

![MainStay Suites Dover](https://images.trvl-media.com/lodging/2000000/1940000/1932400/1932345/d8044825_y.jpg)

### MainStay Suites Dover

6/10 Okay

"The hotel smelled like smoke as soon as you walked in other then that it was okay"

[](https://expedia.ca/Dover-Hotels-MainStay-Suites-Dover.h1932345.Hotel-Information)

![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg)

### Comfort Inn & Suites Chestertown

10/10 Excellent

"N/A"

[](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information)

## Find out more about Henderson

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 Henderson. 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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### Trending destinations on Expedia.ca

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- [Vacation Homes in Henderson ](https://expedia.ca/Henderson-Private-Vacation-Homes.d3000440669-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Henderson ](https://expedia.ca/Henderson-Cottages.d3000440669-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Henderson ](https://expedia.ca/Henderson-Apartments.d3000440669-aaApartments.Travel-Guide-Accommodation)
- [Motels in Henderson ](https://expedia.ca/Henderson-Motels.d3000440669-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Henderson ](https://expedia.ca/Henderson-Agritourism.d3000440669-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Henderson ](https://expedia.ca/Henderson-Bed-And-Breakfast.d3000440669-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Henderson ](https://expedia.ca/Henderson-Villas.d3000440669-aaVillas.Travel-Guide-Accommodation)
- [Guest Houses in Henderson ](https://expedia.ca/Henderson-Guest-Houses.d3000440669-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Henderson ](https://expedia.ca/Henderson-Cabins.d3000440669-aaCabins.Travel-Guide-Accommodation)

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