Cheswold Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Cheswold holiday rentals

1 bedroom, desk, iron/ironing board, WiFi
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Apartment in Frederica

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
10.0 out of 10, Exceptional, (17)
"Great place to stay, very clean and spacious. About 20 minutes from the Dover NASCAR race which was perfect. I would absolutely recommend!"
United States
Eric F.
The price is HK$505
HK$1,437 total
includes taxes & fees
30 Dec - 31 Dec
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$528
HK$972 total
includes taxes & fees
31 Dec - 1 Jan 2026
Guest Suite for up to 2 in a Victorian on the Chester River
Dining
Amazing Modern house with a full kitchen and parking

Holiday Home in Smyrna

Amazing Modern house with a full kitchen and parking
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,399
HK$2,767 total
includes taxes & fees
29 Dec - 30 Dec
Amazing Modern house with a full kitchen and parking
Private kitchen
JVA LUXURY HOUSING

Holiday Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is HK$3,109
HK$4,577 total
includes taxes & fees
4 Jan - 5 Jan 2026
JVA LUXURY HOUSING
Microwave, oven, stovetop, dishwasher
Welcoming 3-bedroom house with AC in charming Milford.

Holiday Home in Milford

Welcoming 3-bedroom house with AC in charming Milford.
2.0 star property
The price is HK$2,526
HK$3,867 total
includes taxes & fees
3 Jan - 4 Jan 2026
Welcoming 3-bedroom house with AC in charming Milford.
A heated pool
Heated Pool • Private Backyard • Home Theater

Holiday Home in Middletown

Heated Pool • Private Backyard • Home Theater
2.0 star property
The price is HK$940
HK$4,119 total
includes taxes & fees
12 Jan - 13 Jan 2026
Heated Pool • Private Backyard • Home Theater
Outdoor dining
Spacious 4-bedroom house with backyard oasis

Holiday Home in Middletown

Spacious 4-bedroom house with backyard oasis
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
The price is HK$1,825
HK$8,920 total
includes taxes & fees
7 Jan - 8 Jan 2026
Spacious 4-bedroom house with backyard oasis
Interior
Spacious 5 Bedroom w/Pool, Patio and Theater

Holiday Home in Magnolia

Spacious 5 Bedroom w/Pool, Patio and Theater
9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is HK$2,243
HK$5,422 total
includes taxes & fees
30 Dec - 31 Dec
Spacious 5 Bedroom w/Pool, Patio and Theater
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.
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Top Cheswold Hotel Reviews

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"Yes"
Jane 1-night trip
Posted 19 hours ago
Bally's Dover Casino Resort

Find out more about Cheswold

Search for holiday rentals in Cheswold on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheswold using one of the methods below:

  • View our selection of featured holiday rentals in Cheswold
  • Use the map to find apartments and other holiday homes in the Cheswold neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheswold while they last

Look no further and take a look at our great range of rental properties in Cheswold!

Frequently asked questions

Are there holiday rentals in Cheswold?

Yes, there are holiday rentals close to the most popular sights in Cheswold, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cheswold has to offer?

Charming 3-bedroom Ranch in delightful Dover with AC: This holiday home rental outside of Cheswold has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Cheswold?

While you're exploring the area, Wheel of Fortune and Woodland Beach are a couple of picturesque spots to get outside and enjoy nature. Dover Mall and Delaware State University are a couple of places you'll find in the wider area.

What are holiday rentals like in Cheswold?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheswold. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.