Title: Sleepy Hollow Vacation Rentals from CA $299: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Hotels.d553248634983195824.Travel-Guide-Hotels)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d553248634983195824.Car-Rental-Guide)[Sleepy Hollow Vacation Packages](https://expedia.ca/Sleepy-Hollow.d553248634983195824.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634983195824&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=553248634983195824&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=553248634983195824&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=553248634983195824&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 Sleepy Hollow vacation rentals

![Interior](https://images.trvl-media.com/lodging/120000000/119870000/119860100/119860020/3c956047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119870000/119860100/119860020/f102b0b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119870000/119860100/119860020/19034b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119870000/119860100/119860020/8f410d90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 1-bedroom apartment in fabulous Gillette with AC

[](https://www.expedia.ca/Gillette-Hotels-Charming-1-Bedroom-Apartment-In-Fabulous-Gillette-With-AC.h119860020.Hotel-Information)

Gillette

CA $104

CA $299 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Gillette-Hotels-Charming-1-Bedroom-Apartment-In-Fabulous-Gillette-With-AC.h119860020.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/98000000/97020000/97010400/97010377/d867d050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/98000000/97020000/97010400/97010377/fbdef7e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/98000000/97020000/97010400/97010377/51af8ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sport court](https://images.trvl-media.com/lodging/98000000/97020000/97010400/97010377/35e0d72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!

[](https://www.expedia.ca/Gillette-Hotels-Cozy-5bdrm-Haven-In-The-Heart-Of-Gillette-5-Min-From-Downtown-FREE-Pool-Passes.h97010377.Hotel-Information)

Gillette

10/10

Exceptional

(2 reviews)

"Great location for coming for a soccer tournament. Close enough (5-10 minutes) from everything needed - food, activities, and fun. Lots of space to spread out with a group and a cute yard to play in. Beds were really comfortable with nice bedding and a variety of pillows to fit anyone. A couple different seating areas to hang out and watch TV in the evening. We really enjoyed our stay! Sheri was super responsive and great to work with during our stay! I hope to stay here again when we return."

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

Travis N.

CA $490

CA $873 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Gillette-Hotels-Cozy-5bdrm-Haven-In-The-Heart-Of-Gillette-5-Min-From-Downtown-FREE-Pool-Passes.h97010377.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119134700/119134614/3688fac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119134700/119134614/9ae981e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119140000/119134700/119134614/4d0e8c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119140000/119134700/119134614/594a9770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom townhome in charming Gillette with an unbeatable location.

[](https://www.expedia.ca/Gillette-Hotels-3-Bedroom-Townhome-In-Charming-Gillette-With-An-Unbeatable-Location.h119134614.Hotel-Information)

Gillette

10/10

Exceptional

(6 reviews)

"It was a really nice house with an awesome host and it has everything you need for a comfortable stay. "

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

Bailey G.

CA $207

CA $431 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Gillette-Hotels-3-Bedroom-Townhome-In-Charming-Gillette-With-An-Unbeatable-Location.h119134614.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=2026-03-04&endDate=2026-03-05&regionId=553248634983195824&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

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

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_553248634983195824)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Wyoming%2C+United+States+of+America&regionId=553248634983195824&latLong=44.232009%2C-105.428874&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Wyoming%2C+United+States+of+America&regionId=553248634983195824&latLong=44.232009%2C-105.428874&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VACATION_HOME)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSleepy-Hollow-Vacation-Rentals.d553248634983195824.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSleepy-Hollow-Vacation-Rentals.d553248634983195824.Travel-Guide-VacationRentals)

## Top Sleepy Hollow Hotel Reviews

![Quality Inn Gillette I-90 East](https://images.trvl-media.com/lodging/1000000/50000/43200/43155/d5805c37_y.jpg)

### Quality Inn Gillette I-90 East

10/10 Excellent

"Great value! "

[](https://expedia.ca/Gillette-Hotels-Quality-Inn.h43155.Hotel-Information)

![TownePlace Suites by Marriott Gillette](https://images.trvl-media.com/lodging/16000000/15480000/15478500/15478431/5683a08c_y.jpg)

### TownePlace Suites by Marriott Gillette

10/10 Excellent

"Room was great employees were friendly."

[](https://expedia.ca/Gillette-Hotels-TownePlace-Suites-By-Marriott-Gillette.h15478431.Hotel-Information)

![Wingate by Wyndham Gillette](https://images.trvl-media.com/lodging/1000000/860000/851900/851801/cc4ec91a_y.jpg)

### Wingate by Wyndham Gillette

10/10 Excellent

"Great staff. Nice spacious room. Walking distance to many restaurants. "

[](https://expedia.ca/Gillette-Hotels-Wingate-By-Wyndham-Gillette.h851801.Hotel-Information)

![Days Inn by Wyndham Gillette](https://images.trvl-media.com/lodging/1000000/10000/3800/3730/275d741b_y.jpg)

### Days Inn by Wyndham Gillette

10/10 Excellent

"Always a nice stay here and priced good!"

[](https://expedia.ca/Gillette-Hotels-Days-Inn-By-Wyndham-Gillette.h3730.Hotel-Information)

![Garner Hotel Gillette South by IHG](https://images.trvl-media.com/lodging/3000000/2620000/2614800/2614729/1e7c4937_y.jpg)

### Garner Hotel Gillette South by IHG

10/10 Excellent

"We always stay here. The staff is great, rooms are clean, and the pool is a blast! "

[](https://expedia.ca/Gillette-Hotels-Country-Inn-Suites-By-Radisson.h2614729.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Gillette](https://images.trvl-media.com/lodging/15000000/15000000/14991000/14990975/3bce9929_y.jpg)

### La Quinta Inn & Suites by Wyndham Gillette

10/10 Excellent

"Friendly staff. Clean all the time"

[](https://expedia.ca/Gillette-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Gillette.h14990975.Hotel-Information)

![Summit Suites](https://images.trvl-media.com/lodging/1000000/900000/892600/892583/d090923a_y.jpg)

### Summit Suites

10/10 Excellent

"Amazing Hotel! "

[](https://expedia.ca/Gillette-Hotels-Summit-Suites.h892583.Hotel-Information)

![Comfort Inn & Suites Gillette near Campbell Medical Center](https://images.trvl-media.com/lodging/1000000/980000/970800/970789/94c29bc9_y.jpg)

### Comfort Inn & Suites Gillette near Campbell Medical Center

10/10 Excellent

"Clean room great breakfast!! Good service "

[](https://expedia.ca/Gillette-Hotels-Comfort-Inn-Suites-Gillette-Near-Campbell-Medical-Center.h970789.Hotel-Information)

![Red Lion Hotel Gillette](https://images.trvl-media.com/lodging/104000000/103530000/103524700/103524687/b2e8d9b6_y.jpg)

### Red Lion Hotel Gillette

10/10 Excellent

"I liked the room and the check in and out was easy"

[](https://expedia.ca/Gillette-Hotels-Red-Lion-Hotel-Gillette.h103524687.Hotel-Information)

## Find out more about Sleepy Hollow

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 Sleepy Hollow. 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.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Sleepy Hollow

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Sleepy Hollow ](https://expedia.ca/Sleepy-Hollow-Private-Vacation-Homes.d553248634983195824-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Motels in Sleepy Hollow ](https://expedia.ca/Sleepy-Hollow-Motels.d553248634983195824-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Sleepy Hollow ](https://expedia.ca/Sleepy-Hollow-RV-Parks.d553248634983195824-aaRVParks.Travel-Guide-Accommodation)
- [Apartments in Sleepy Hollow ](https://expedia.ca/Sleepy-Hollow-Apartments.d553248634983195824-aaApartments.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Sleepy Hollow?

### What's the top vacation rental in Sleepy Hollow?

### What’s there to see and do in Sleepy Hollow?

### What’s a vacation rental in Sleepy Hollow like?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app