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Cheswold Holiday Rentals

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Our top choices for Cheswold holiday rentals

1. 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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is NZ$329
includes taxes & fees
8 Oct - 9 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

2. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is NZ$446
includes taxes & fees
27 Oct - 28 Oct
Mini Aruba RV/Glamping Tent

3. 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, (28 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 NZ$222
includes taxes & fees
5 Oct - 6 Oct
Guest Suite for up to 2 in a Victorian on the Chester River

4. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
The price is NZ$960
includes taxes & fees
6 Oct - 7 Oct
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is NZ$325
includes taxes & fees
13 Oct - 14 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

6. 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 NZ$669
includes taxes & fees
18 Oct - 19 Oct
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

7. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 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

8. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
The price is NZ$1,299
includes taxes & fees
4 Oct - 5 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat

9. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
The price is NZ$1,271
includes taxes & fees
4 Oct - 5 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat

10. 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, (6 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 NZ$879
includes taxes & fees
2 Oct - 3 Oct
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

Find out more about Cheswold

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cheswold holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cheswold. 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 Cheswold. 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 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 holiday 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 Cheswold short-term rentals, that won’t be hard to do.

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 Little Creek Wildlife Area 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.