Cheswold Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Cheswold holiday rentals

Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3 Mi to Dover Motor Speedway: Pet-friendly Retreat
3.0 star property
Dover
The price is HK$729
HK$3,340 total
includes taxes & fees
29 Apr - 30 Apr
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 reviews)
"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$1,099
HK$2,386 total
includes taxes & fees
17 Apr - 18 Apr
Amazing Modern house with a full kitchen and parking
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$533
HK$980 total
includes taxes & fees
27 Apr - 28 Apr
Guest Suite for up to 2 in a Victorian on the Chester River
3 bedrooms, WiFi, bed sheets

Welcoming 3-bedroom house with AC in charming Milford.

Welcoming 3-bedroom house with AC in charming Milford.
Milford
The price is HK$2,546
HK$3,922 total
includes taxes & fees
24 Apr - 25 Apr
Welcoming 3-bedroom house with AC in charming Milford.
Interior

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is HK$3,133
HK$4,559 total
includes taxes & fees
22 Apr - 23 Apr
JVA LUXURY HOUSING
Interior

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
The price is HK$1,371
HK$1,918 total
includes taxes & fees
12 May - 13 May
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Fridge, microwave, oven, stovetop

Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.8 out of 10, Exceptional, (8 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
Spacious 5 Bedroom w/Pool, Patio and Theater
1 bedroom, desk, iron/ironing board, WiFi

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
10.0 out of 10, Exceptional, (19 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
The price is HK$509
HK$1,433 total
includes taxes & fees
19 Apr - 20 Apr
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Beach

Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf

Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf
Dover
The price is HK$1,375
HK$2,753 total
includes taxes & fees
17 Apr - 18 Apr
Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf
Interior

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Dover
The price is HK$1,551
HK$2,694 total
includes taxes & fees
20 Apr - 21 Apr
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
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
"Stayed for an overnight work trip. Wonderful experience checking in, room was clean and provided everything I needed. Nice to have restaurants and other things to do on site, will definitely come back!"
Kaylee 1-night trip
Posted 2 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
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  • 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?

Bowers Retreat - Sleeps 10 - Steps to beach & bars! 10 Minutes to DE Turf!: This holiday home rental outside of Cheswold is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Cheswold?

While you're exploring the area, Wheel of Fortune and First State Heritage Park 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.