Title: Cheswold Vacation Rentals from CA $660: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Cheswold](https://expedia.ca/Cheswold-Hotels.d553248634999403720.Travel-Guide-Hotels)[Cheswold Car Rentals](https://expedia.ca/Car-Rentals-In-Cheswold.d553248634999403720.Car-Rental-Guide)[Cheswold Vacation Packages](https://expedia.ca/Cheswold.d553248634999403720.Destination-Travel-Guides)

![Liberty and Independence Monument, Dover Delaware USA, Dover, Delaware](https://images.trvl-media.com/place/553248634999403720/5480b2fc-2bb7-400f-b904-8ca897053fc9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248634999403720/5480b2fc-2bb7-400f-b904-8ca897053fc9.jpg?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

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248634999403720&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=553248634999403720&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=553248634999403720&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999403720&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)

![](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_553248634999403720)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Cheswold%2C+Delaware%2C+United+States+of+America&regionId=553248634999403720&latLong=39.221427%2C-75.582978&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Cheswold%2C+Delaware%2C+United+States+of+America&regionId=553248634999403720&latLong=39.221427%2C-75.582978&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Cheswold%2C+Delaware%2C+United+States+of+America&regionId=553248634999403720&latLong=39.221427%2C-75.582978&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Cheswold%2C+Delaware%2C+United+States+of+America&regionId=553248634999403720&latLong=39.221427%2C-75.582978&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Cheswold%2C+Delaware%2C+United+States+of+America&regionId=553248634999403720&latLong=39.221427%2C-75.582978&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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%2FCheswold-Vacation-Rentals.d553248634999403720.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheswold-Vacation-Rentals.d553248634999403720.Travel-Guide-VacationRentals)

## Top Cheswold Hotel Reviews

![Microtel Inn & Suites by Wyndham Dover](https://images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg)

### Microtel Inn & Suites by Wyndham Dover

10/10 Excellent

"yes"

[](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.Hotel-Information)

![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg)

### Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent

"Everything was exceptional!"

[](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

![Comfort Inn & Suites Dover near Speedway](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60_y.jpg)

### Comfort Inn & Suites Dover near Speedway

10/10 Excellent

"Clean rooms and friendly staff "

[](https://expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information)

![Bally's Dover Casino Resort](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg)

### Bally's Dover Casino Resort

10/10 Excellent

"Great experience! Staff was extremely helpful as needed some help with printing a document."

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

![Hampton Inn Middletown](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe_y.jpg)

### Hampton Inn Middletown

10/10 Excellent

"The gentleman at the front desk was the absolute best. The breakfast attendant kept such a clean, organized, well-stocked area with delicious options with plenty of variety. Room was comfortable, clean, and wonderfully pet-friendly. "

[](https://expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information)

![Residence Inn Marriott Dover](https://images.trvl-media.com/lodging/2000000/1720000/1710800/1710788/b77a1ac6_y.jpg)

### Residence Inn Marriott Dover

10/10 Excellent

"Yes."

[](https://expedia.ca/Dover-Hotels-Residence-Inn-Marriott-Dover.h1710788.Hotel-Information)

![Holiday Inn Express & Suites Middletown by IHG](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131_y.jpg)

### Holiday Inn Express & Suites Middletown by IHG

10/10 Excellent

"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"

[](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

![Holiday Inn Express Hotel & Suites Dover by IHG](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg)

### Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

"Very Nice looking forward to returning in a couple weeks "

[](https://expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information)

![Wyndham Garden Dover](https://images.trvl-media.com/lodging/1000000/530000/520100/520035/cf1236f9_y.jpg)

### Wyndham Garden Dover

10/10 Excellent

"Clean room, helpful staff. "

[](https://expedia.ca/Dover-Hotels-Wyndham-Garden-Dover.h520035.Hotel-Information)

## Find out more about Cheswold

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 Cheswold. 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 Cheswold

### 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 Cheswold ](https://expedia.ca/Cheswold-Private-Vacation-Homes.d553248634999403720-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Cheswold ](https://expedia.ca/Cheswold-Cottages.d553248634999403720-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Cheswold ](https://expedia.ca/Cheswold-Apartments.d553248634999403720-aaApartments.Travel-Guide-Accommodation)
- [Motels in Cheswold ](https://expedia.ca/Cheswold-Motels.d553248634999403720-aaMotels.Travel-Guide-Accommodation)
- [B&B in Cheswold ](https://expedia.ca/Cheswold-Bed-And-Breakfast.d553248634999403720-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Cheswold ](https://expedia.ca/Cheswold-Agritourism.d553248634999403720-aaAgritourism.Travel-Guide-Accommodation)
- [Guest Houses in Cheswold ](https://expedia.ca/Cheswold-Guest-Houses.d553248634999403720-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in Cheswold ](https://expedia.ca/Cheswold-Condos.d553248634999403720-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Cheswold ](https://expedia.ca/Cheswold-Cabins.d553248634999403720-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Cheswold?

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

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

### What are vacation rentals like in Cheswold?

![](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