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Cheswold Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Cheswold holiday rentals

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
9.8 out of 10, Exceptional, (8 reviews)
"Woodland Hideaway was just that! A nice place to hideaway after hot and busy days. The place was clean, kitchen well stocked and the whole unit was quiet. It was located in a nice subdivision with lots of trees and beautiful flowers. It was the first trip my husband and I took our dog and it was a great place for the dog, quiet with lots of places for his daily walks. Thank you Kara!"
United States
Melanie
The price is HK$706
HK$1,208 total
includes taxes & fees
17 Aug - 18 Aug
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Pool

Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is HK$1,670
HK$2,521 total
includes taxes & fees
26 Jul - 27 Jul
Mini Aruba RV/Glamping Tent
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
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is HK$533
HK$981 total
includes taxes & fees
20 Jul - 21 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

Cozy Room in Dover

Cozy Room in Dover
Dover
The price is HK$459
HK$754 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Room in Dover
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
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is HK$1,905
HK$3,143 total
includes taxes & fees
26 Jul - 27 Jul
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
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, (21 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
The price is HK$706
HK$1,670 total
includes taxes & fees
19 Jul - 20 Jul
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Coffee/tea maker, fridge, microwave, oven

Come stay at our beautiful 3 bedroom home located in rural Milford De.

Come stay at our beautiful 3 bedroom home located in rural Milford De.
Milford
10.0 out of 10, Exceptional, (4 reviews)
"The guys went to the race and they were very happy with the location the price and the people were very nice to deal with"
United States
debra h.
The price is HK$2,548
HK$3,901 total
includes taxes & fees
21 Jul - 22 Jul
Come stay at our beautiful 3 bedroom home located in rural Milford De.
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

8/10 Good
"Very clean rooms and the casino is nice"
Robert 1-night trip
Posted 3 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?

Captain's Quarters: This holiday home rental outside of Cheswold is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 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, Silver Lake Park 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.