Title: Middletown Vacation Home Rentals from CA $298: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Washington Monument](https://images.trvl-media.com/place/6351200/c824f6fe-887c-4c10-9f1a-99abbb2720b8.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Middletown Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6351200&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6351200&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6351200&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 four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6351200&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middletown vacation homes

![Exterior](https://images.trvl-media.com/lodging/43000000/42350000/42342000/42341954/da4a4dbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/43000000/42350000/42342000/42341954/4cb06908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/43000000/42350000/42342000/42341954/daeee4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/43000000/42350000/42342000/42341954/74a37f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming "Cream of the Crop" Cape \~❤️of Middletown

[](https://www.expedia.ca/Frederick-Hotels-Vrbo-Property.h42341954.Hotel-Information)

Middletown

10/10

Exceptional

(139)

"Love the place will book again"

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

WAYNE M.

CA $173

CA $389 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Frederick-Hotels-Vrbo-Property.h42341954.Hotel-Information)

![](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/0ed0ba48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/e79a9faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/7d8e3efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/1c679d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

[](https://www.expedia.ca/Frederick-Hotels-RETREAT-On-The-CREEK-Businees-Travelor-Or-Weekend-Getaway-HISTORIC-DISTRICT.h21298018.Hotel-Information)

Downtown Frederick

9.4/10

Exceptional

(119)

"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "

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

Natalie C.

CA $154

CA $383 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Frederick-Hotels-RETREAT-On-The-CREEK-Businees-Travelor-Or-Weekend-Getaway-HISTORIC-DISTRICT.h21298018.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/60000000/59860000/59852500/59852480/fde9a8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59860000/59852500/59852480/28499d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/60000000/59860000/59852500/59852480/e9b96744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59860000/59852500/59852480/e7841b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*Luxury Condo In Downtown Frederick\*

[](https://www.expedia.ca/Frederick-Hotels-Luxury-Condo-In-Downtown-Frederick.h59852480.Hotel-Information)

Downtown Frederick

9.0/10

Wonderful

(71)

"Great time. Everything was perfect and place was just what we needed. "

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

dominick c.

CA $141

CA $360 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Frederick-Hotels-Luxury-Condo-In-Downtown-Frederick.h59852480.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122020000/122010800/122010723/797d2a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122020000/122010800/122010723/8ede81af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122020000/122010800/122010723/5289ebe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122020000/122010800/122010723/a904e5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New, Contemporary House in Historic Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-New.h122010723.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(1)

"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "

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

Erin J.

CA $138

CA $512 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Harpers-Ferry-Hotels-New.h122010723.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66250000/66249900/66249867/34101a08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66250000/66249900/66249867/f5bcc5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66250000/66249900/66249867/881c4f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66250000/66249900/66249867/f15e09fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

[](https://www.expedia.ca/Frederick-Hotels-Welcome-To-The-Rusty-Rose-Restored-Farmhouse-Feel-In-The-Heart-Of-Jefferson.h66249867.Hotel-Information)

Jefferson

9.8/10

Exceptional

(58)

"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"

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

David F.

CA $173

CA $389 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Frederick-Hotels-Welcome-To-The-Rusty-Rose-Restored-Farmhouse-Feel-In-The-Heart-Of-Jefferson.h66249867.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118757800/118757743/3b9ae191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118757800/118757743/w1272h854x0y0-05b98920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118760000/118757800/118757743/9fd72434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118760000/118757800/118757743/38fbb61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Queen Anne Family Home w Modern Comforts

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Historic-Queen-Anne-Home-W-Modern-Comforts.h118757743.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(3)

"The location was great and the host was very east to communicate with."

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

Liz B.

CA $221

CA $528 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Historic-Queen-Anne-Home-W-Modern-Comforts.h118757743.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/83000000/82500000/82490800/82490728/fe25a8cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/83000000/82500000/82490800/82490728/e8739af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/83000000/82500000/82490800/82490728/bd6cf7a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/83000000/82500000/82490800/82490728/e64ccd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

[](https://www.expedia.ca/Frederick-Hotels-Gorgeous-Boho-Chic-Apt.h82490728.Hotel-Information)

Frederick

10/10

Exceptional

(34)

"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"

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

Jennifer S.

CA $152

CA $364 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Frederick-Hotels-Gorgeous-Boho-Chic-Apt.h82490728.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87750000/87741700/87741677/a4c3196a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87750000/87741700/87741677/eed243e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87750000/87741700/87741677/9020e378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87750000/87741700/87741677/e05a7fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### White House Inn - Historic Home in Harpers Ferry!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-White-House-Inn-Sprawling-Historic-Home-In-Downtown-Harpers-Ferry.h87741677.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(38)

"Very clean and well appointed. Great for a large group. "

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

Richard

CA $138

CA $561 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Harpers-Ferry-Hotels-White-House-Inn-Sprawling-Historic-Home-In-Downtown-Harpers-Ferry.h87741677.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/570094cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/ce3fb402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/7c2ef18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/51000000/50680000/50679500/50679492/18a05c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage on King | Charming Historic Leesburg Home

[](https://www.expedia.ca/Leesburg-Hotels-Cottage-On-King-Charming-Historic-Leesburg-Home.h50679492.Hotel-Information)

Leesburg's Old and Historic District

9.6/10

Exceptional

(67)

"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"

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

Fern

CA $217

CA $462 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Leesburg-Hotels-Cottage-On-King-Charming-Historic-Leesburg-Home.h50679492.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/43000000/42190000/42190000/42189911/9787d638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/43000000/42190000/42190000/42189911/c177c1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42190000/42190000/42189911/db59b128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/43000000/42190000/42190000/42189911/f90292f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

[](https://www.expedia.ca/Myersville-Hotels-Historic-Cozy-Farmhouse-In-The-Of-Myersville.h42189911.Hotel-Information)

Myersville

9.4/10

Exceptional

(110)

"Alot of choices for food and snacks within walking distance. "

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

Cherilyn H.

CA $220

CA $409 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Myersville-Hotels-Historic-Cozy-Farmhouse-In-The-Of-Myersville.h42189911.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/93000000/92070000/92063300/92063288/a6a47172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92070000/92063300/92063288/d50e8da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92070000/92063300/92063288/29aeccdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92070000/92063300/92063288/8f8ddabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New townhouse

[](https://www.expedia.ca/Frederick-Hotels-New-Townhouse.h92063288.Hotel-Information)

Frederick

9.4/10

Exceptional

(9)

"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"

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

Traci U.

CA $209

CA $499 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Frederick-Hotels-New-Townhouse.h92063288.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/9c57473e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/0a99747a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/beb9f8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113840000/113835900/113835823/c262f123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(5)

"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"

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

Vinod B.

CA $111

CA $421 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountain-Chic-Retreat-Harpers-Ferry.h113835823.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117190000/117187000/117186982/963856dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117190000/117187000/117186982/f8a76fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117190000/117187000/117186982/18cea779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117190000/117187000/117186982/355dfe07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom townhome in charming Hagerstown with AC, WiFi

[](https://www.expedia.ca/Hagerstown-Hotels-3-Bedroom-Townhome-In-Charming-Hagerstown-With-AC.h117186982.Hotel-Information)

Hagerstown

6.0/10

(1)

"The inside was very clean, outside was a mess. Location was bad, on a busy street and a busy railway."

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

mark C.

CA $152

CA $298 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Hagerstown-Hotels-3-Bedroom-Townhome-In-Charming-Hagerstown-With-AC.h117186982.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89350000/89349400/89349390/033f7a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89350000/89349400/89349390/dda2c912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89350000/89349400/89349390/a395e200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Casino](https://images.trvl-media.com/lodging/90000000/89350000/89349400/89349390/990f722c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

[](https://www.expedia.ca/Sharpsburg-Hotels-Incredible-Views-Steps-To-Battlefield-Winery.h89349390.Hotel-Information)

Sharpsburg

10/10

Exceptional

(39)

"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"

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

Jo W.

CA $180

CA $444 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Sharpsburg-Hotels-Incredible-Views-Steps-To-Battlefield-Winery.h89349390.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/47000000/46560000/46559800/46559723/94be8989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/47000000/46560000/46559800/46559723/7ba5d157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/47000000/46560000/46559800/46559723/8af1d6f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/47000000/46560000/46559800/46559723/aed6ff34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Terra Alta - Incredible River Views and Hot Tub!

[](https://www.expedia.ca/Charles-Town-Hotels-Terra-Alta-Hilltop-House-Overlooking-Shenandoah-Rapids.h46559723.Hotel-Information)

Charles Town

9.6/10

Exceptional

(65)

"It was a great house for a weekend getaway. Most of the house was clean. The exterior was a little unkept. A few repairs would be good for the exterior. Everything was functional. The bed was great. Hot tub was clean and well maintained. The grill was like new and worked well. I would stay here again. "

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

Lance B.

CA $138

CA $556 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Charles-Town-Hotels-Terra-Alta-Hilltop-House-Overlooking-Shenandoah-Rapids.h46559723.Hotel-Information)

![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108340000/108331300/108331213/5650dc58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108340000/108331300/108331213/4820c9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108340000/108331300/108331213/996eb636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108340000/108331300/108331213/32229641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Eclectic-Romantic-Walk-To-Historic-Downtown-Harpers-Ferry.h108331213.Hotel-Information)

Harpers Ferry

10/10

Exceptional

(15)

"Great spot"

![China](https://a.travel-assets.com/egds/marks/flags/cn.svg)

Clara

CA $249

CA $427 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Eclectic-Romantic-Walk-To-Historic-Downtown-Harpers-Ferry.h108331213.Hotel-Information)

![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/49c841ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/f943ceaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/82afadcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, table tennis](https://images.trvl-media.com/lodging/113000000/112590000/112582500/112582495/861e2e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Charming-3-Bedroom-House-With-Firepit-And-Game-Room-In-Gorgeous-Harpers-Ferry.h112582495.Hotel-Information)

Harpers Ferry

9.4/10

Exceptional

(19)

"A nice relaxing place to stay in the mountains of WV near many things to do. Check-in and check-out instructions were easy to follow. "

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

L G.

CA $230

CA $593 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Charming-3-Bedroom-House-With-Firepit-And-Game-Room-In-Gorgeous-Harpers-Ferry.h112582495.Hotel-Information)

![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/92000000/91270000/91260900/91260888/12e8e5bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91270000/91260900/91260888/a2e22655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91270000/91260900/91260888/36e645fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91270000/91260900/91260888/a1708278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Leesburg Hideaway- King Bed + Private Backyard

[](https://www.expedia.ca/Leesburg-Hotels-Historic-Hideaway.h91260888.Hotel-Information)

Leesburg

10/10

Exceptional

(30)

"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"

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

Rachael B.

CA $187

CA $422 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Leesburg-Hotels-Historic-Hideaway.h91260888.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71520000/71517500/71517453/6b0e3c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71520000/71517500/71517453/e03b07bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71520000/71517500/71517453/a8e63392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, offices](https://images.trvl-media.com/lodging/72000000/71520000/71517500/71517453/cd7d0472.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enchanting Cottage, walk to Downtown Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Enchanting-Cottage.h71517453.Hotel-Information)

Harpers Ferry

9.6/10

Exceptional

(44)

"We really enjoyed our stay here, the location is perfect for exploring Harpers Ferry, within walking distance to everything. The cottage is well equipped, clean and cozy, perfect for a couples get away, would book again if returning to HF. The owner was very communicated, had well organized info for the stay and was easy to work with"

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

Brandon L.

CA $216

CA $389 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Enchanting-Cottage.h71517453.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103720000/103719300/103719242/058f2d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/104000000/103720000/103719300/103719242/w448h683x289y0-f394eac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103720000/103719300/103719242/f08d552a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103720000/103719300/103719242/58a44967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Peaceful Basement Cabin Vibes

[](https://www.expedia.ca/Ijamsville-Hotels-Cozy-Peaceful-Basement-Cabin-Vibes.h103719242.Hotel-Information)

Ijamsville

10/10

Exceptional

(5)

"Good trip."

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

Jewell F.

CA $346

CA $500 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Ijamsville-Hotels-Cozy-Peaceful-Basement-Cabin-Vibes.h103719242.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=2025-12-25&endDate=2025-12-26&regionId=6351200&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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Cabins

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Cottages

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Condos

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Villas

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Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+Maryland%2C+United+States+of+America&regionId=6351200&latLong=39.443714%2C-77.544708&adults=2&startDate=2026-03-10&d1=2026-03-10&endDate=2026-03-13&d2=2026-03-13&lodging=CHALET)

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## Top Middletown Hotel Reviews

![Country Inn & Suites by Radisson, Frederick, MD](https://images.trvl-media.com/lodging/1000000/60000/59600/59588/6e927b9b_y.jpg)

### Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent

"Everything was great! "

[](https://expedia.ca/Frederick-Hotels-Country-Inn-Suites-By-Radisson.h59588.Hotel-Information)

![Red Roof Inn Leesburg, VA](https://images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg)

### Red Roof Inn Leesburg, VA

10/10 Excellent

" Needed a room for one night while visiting my daughter at college in Purcellville and to attend a church service at Cornerstone Chapel in Leesburg. This hotel was convenient as well as the most economical in Leesburg having good ratings. It turned out great! Must have recently been updated because it was very clean and comfortable. The staff member at the desk for my late night checkin and early morning checkout had a great attitude, professional at the same time friendly and welcoming! Thank you, Red Roof Inn and thank you to your staff member!"

[](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information)

![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg)

### Holiday Inn Express Charles Town by IHG

10/10 Excellent

"Everything was great"

[](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information)

![SpringHill Suites by Marriott Frederick](https://images.trvl-media.com/lodging/62000000/61640000/61631900/61631879/e35ce686_y.jpg)

### SpringHill Suites by Marriott Frederick

10/10 Excellent

"Yes"

[](https://expedia.ca/Frederick-Hotels-SpringHill-Suites-By-Marriott-Frederick.h61631879.Hotel-Information)

![Tru By Hilton Martinsburg](https://images.trvl-media.com/lodging/103000000/102720000/102710100/102710055/0ce58ab1_y.jpg)

### Tru By Hilton Martinsburg

10/10 Excellent

"Friendly staff, very clean rooms. Breakfast was really good. Loves they had games and a pool table. Close to alot of restaurants making it convenient. "

[](https://expedia.ca/Martinsburg-Hotels-Tru-By-Hilton-Martinsburg.h102710055.Hotel-Information)

![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/d621c756_y.jpg)

### Best Western Leesburg Hotel & Conference Center

10/10 Excellent

"Ok"

[](https://expedia.ca/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information)

![Country Inn & Suites by Radisson, Hagerstown, MD](https://images.trvl-media.com/lodging/2000000/1220000/1216300/1216228/31529ad2_y.jpg)

### Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent

"Getting to the hotel was a little confusing as it is deep in a shopping center, but once we arrived everything was wonderful. Everything was spotless, service was kind and enthusiastic, breakfast was great, and the entire stay was pleasant and smooth."

[](https://expedia.ca/Hagerstown-Hotels-Country-Inn-Suites-By-Radisson.h1216228.Hotel-Information)

![Hampton Inn Hagerstown](https://images.trvl-media.com/lodging/1000000/60000/59800/59778/w3840h2557x0y3-59fd052e_y.jpg)

### Hampton Inn Hagerstown

10/10 Excellent

"We did not stay for breakfast "

[](https://expedia.ca/Hagerstown-Hotels-Hampton-Inn-Hagerstown.h59778.Hotel-Information)

![Clarion Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90_y.jpg)

### Clarion Inn Harpers Ferry - Charles Town

10/10 Excellent

"Very nice people in the front desk"

[](https://expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information)

## Find out more about Middletown

## Middletown Vacation Homes information

| Number of reviews | 858                |
| ----------------- | ------------------ |
| Accommodation     | 259 Vacation Homes |
| Lowest Price      | CA $298            |
| Highest Price     | CA $593            |

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- [Flights to Boonsboro ](https://www.expedia.ca/Cheap-Flights-To-Boonsboro.d3000440431.Travel-Guide-Flights)
- [Flights to Frederick ](https://www.expedia.ca/Cheap-Flights-To-Frederick.d6057476.Travel-Guide-Flights)
- [Flights from Burkittsville ](https://www.expedia.ca/lp/flights/3000347825/flights-from-burkittsville)
- [Flights from Frederick ](https://www.expedia.ca/lp/flights/6057476/flights-from-frederick)

- [Frederick Vacations ](https://www.expedia.ca/Frederick.d6057476.Destination-Travel-Guides)
- [Greenbrier State Park ](https://www.expedia.ca/Greenbrier-State-Park-Boonsboro.d553248621532662571.Vacation-Attraction)

- [Avis Rental Cars in Frederick ](https://www.expedia.ca/Avis-Car-Rentals-In-Frederick.d6057476-c41.Car-Rental-Guide-Suppliers)
- [Car rental Frederick ](https://www.expedia.ca/Car-Rentals-In-Frederick.d6057476.Car-Rental-Guide)

- [Frederick Vacation Rentals ](https://www.expedia.ca/Frederick-Vacation-Rentals.d6057476.Travel-Guide-VacationRentals)

- [Book Vacation Homes in Middletown on Expedia.com ](https://www.expedia.com/Middletown-Private-Vacation-Homes.d6351200-aaPrivateVacationHomes.Travel-Guide-Accommodation)