Title: Tollesboro Vacation Rentals from CA $155: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Tollesboro](https://expedia.ca/Tollesboro-Hotels.d3000347489.Travel-Guide-Hotels)[Tollesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Tollesboro.d3000347489.Car-Rental-Guide)[Tollesboro Vacation Packages](https://expedia.ca/Tollesboro.d3000347489.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=3000347489&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=3000347489&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=3000347489&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=3000347489&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)

![](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_3000347489)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Tollesboro%2C+Kentucky%2C+United+States+of+America&regionId=3000347489&latLong=38.535%2C-83.5605&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Tollesboro%2C+Kentucky%2C+United+States+of+America&regionId=3000347489&latLong=38.535%2C-83.5605&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Tollesboro%2C+Kentucky%2C+United+States+of+America&regionId=3000347489&latLong=38.535%2C-83.5605&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=Tollesboro%2C+Kentucky%2C+United+States+of+America&regionId=3000347489&latLong=38.535%2C-83.5605&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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%2FTollesboro-Vacation-Rentals.d3000347489.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTollesboro-Vacation-Rentals.d3000347489.Travel-Guide-VacationRentals)

## Top Tollesboro Hotel Reviews

![Quality Inn Maysville](https://images.trvl-media.com/lodging/1000000/20000/17100/17042/5a32ce9b_y.jpg)

### Quality Inn Maysville

10/10 Excellent

"We arrived late in the evening due to the inclement weather. There was someone at the front desk who checked us in and had us on our way up to our room in five minutes. The room was exactly as advertised. Everything was clean and well-stocked. "

[](https://expedia.ca/Maysville-Hotels-Quality-Inn-Maysville-Area.h17042.Hotel-Information)

![Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State ](https://images.trvl-media.com/lodging/97000000/96340000/96339700/96339673/90a1bf9d_y.jpg)

### Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State 

10/10 Excellent

"Everything at the cottage was great. Clean as always and everything that you need for a relaxed weekend. "

[](https://expedia.ca/Morehead-Hotels-Cozy-Sunset-Cottage-On-The-Family-Farm-Near-Cave-Run-Lake-And-Morehead-State.h96339673.Hotel-Information)

![Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!](https://images.trvl-media.com/lodging/112000000/111660000/111652700/111652604/009ac7b4_y.jpg)

### Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

10/10 Excellent

"The decor was amazing. The host was very responsive and on the ball."

[](https://expedia.ca/Dover-Hotels-Experience-Peace.h111652604.Hotel-Information)

![Days Inn by Wyndham Maysville Kentucky](https://images.trvl-media.com/lodging/1000000/30000/25500/25466/032fdf94_y.jpg)

### Days Inn by Wyndham Maysville Kentucky

10/10 Excellent

"100 % muy bueno "

[](https://expedia.ca/Maysville-Hotels-Days-Inn-By-Wyndham-Maysville-Kentucky.h25466.Hotel-Information)

![French Quarter Inn](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/w1000h451x0y0-8ba0d251_y.jpg)

### French Quarter Inn

10/10 Excellent

"staff great"

[](https://expedia.ca/Maysville-Hotels-French-Quarter-Inn.h15589406.Hotel-Information)

![Beverly hills inn](https://images.trvl-media.com/lodging/109000000/108730000/108721700/108721615/2ca35418_y.jpg)

### Beverly hills inn

10/10 Excellent

"Perfect"

[](https://expedia.ca/Aberdeen-Hotels-Beverly-Hills-Inn.h108721615.Hotel-Information)

![Cozy private getaway built for couples to reconnect !! ](https://images.trvl-media.com/lodging/100000000/99850000/99846400/99846345/c709cc75_y.jpg)

### Cozy private getaway built for couples to reconnect !! 

10/10 Excellent

"Great place to get away. House was clean, nicely setup, and as good or better than the pictures! Make sure you take note that there isn’t internet service. Hope to return. "

[](https://expedia.ca/West-Union-Hotels-Cozy-Private-Getaway-Built-For-Couples-To-Reconnect.h99846345.Hotel-Information)

![Spacious 4-bedroom 19th Century home in historic downtown Maysville!](https://images.trvl-media.com/lodging/114000000/113540000/113533400/113533366/7eb05faa_edited_2771_y.jpg)

### Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10/10 Excellent

"Sarah, our host, was very responsive. The listing was accurately described. We will definitely book again."

[](https://expedia.ca/Maysville-Hotels-Spacious-4-Bedroom-19th-Century-Home-In-Historic-Downtown-Maysville.h113533366.Hotel-Information)

![Secluded cabin located in Amish country ](https://images.trvl-media.com/lodging/73000000/72390000/72387500/72387492/ecfe8fca_y.jpg)

### Secluded cabin located in Amish country 

10/10 Excellent

"Everything was absolutely beautiful! My husband and i booked as a Christmas weekend getaway and it was just what we needed! The peace and quiet was perfection"

[](https://expedia.ca/West-Union-Hotels-Secluded-Cabin-Located-In-Amish-Country.h72387492.Hotel-Information)

## Find out more about Tollesboro

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 Tollesboro. 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 Tollesboro

### 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)

- [Cabin Rentals in Tollesboro ](https://expedia.ca/Tollesboro-Cabins.d3000347489-aaCabins.Travel-Guide-Accommodation)
- [Vacation Homes in Tollesboro ](https://expedia.ca/Tollesboro-Private-Vacation-Homes.d3000347489-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Tollesboro ](https://expedia.ca/Tollesboro-Apartments.d3000347489-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Tollesboro ](https://expedia.ca/Tollesboro-Cottages.d3000347489-aaCottages.Travel-Guide-Accommodation)
- [Motels in Tollesboro ](https://expedia.ca/Tollesboro-Motels.d3000347489-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Tollesboro ](https://expedia.ca/Tollesboro-Agritourism.d3000347489-aaAgritourism.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Tollesboro?

### What's the top vacation rental that Tollesboro has to offer?

### What can I see and do in Tollesboro?

### What are vacation rentals like in Tollesboro?

![](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