Cheswold Holiday Rentals

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Holiday Rentals in Cheswold

Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Captain's Quarters
9.8 out of 10, Exceptional, (67)
"We stayed in Bowers for a lacrosse tournament at DE Turf Fields; I recommend it - very convenient! The house and location made it more like a vacation than a tournament weekend 🙂. Great access to the water. The property manager was very responsive and accommodating!"
Captain's Quarters
Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, (14)
"Was the most relaxing vacation ever. The best front porch and great bay views. Loved all the spawning horseshoe crabs! Will definitely come again."
Wind Song Getaway on the Beach
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Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
The price is AU$1,557
per night
6 July - 7 July
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, (4)
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Bowers Beach Vacation Rental: 2 Blocks Away!
10.0 out of 10, Exceptional, (1)
"Great place for us. Appreciate the bottled water dispenser and extra water bottle. Only thing I could say that was negative was the master bed mattress was way too soft and gave my wife and I some neck soreness. All in all we really enjoyed our stay."
Bowers Beach Vacation Rental: 2 Blocks Away!
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, (3)
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Modern 4 bdr with King size bed Patio and Late Checkout!
10.0 out of 10, Exceptional, (2)
"Great property!!! Close to the torney we were attending!!"
Modern 4 bdr with King size bed Patio and Late Checkout!
Peaceful country home away in the wilderness
10.0 out of 10, Exceptional, (11)
"This is a beautiful property out in the country, we all loved it! Very clean and comfortable, all the amenities mentioned were readily available. The location was about a 35 minute drive to the speedway which was perfect for us, not too far and not too close. We enjoyed sitting outside on the picnic table and listening to the nature sounds around us and watching the chickens. Access to the home was very easy as well as getting around the area, nothing was too far. It was great fun and felt like...
Peaceful country home away in the wilderness
Blue Room in Delaware
8.0 out of 10, Very good, (1)
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
10.0 out of 10, Exceptional, (6)
"I hosted four teenage boys for a lacrosse tournament in Frederica. Fields were 10 minutes away. It was great staying in a home vs a hotel. Comfy beds. Responsive host. Accommodated our needs for adjusted check out. Big comfy couch and porches as re relaxing set up. Restaurant and food truck were amazing and had live music both nights in parking lot in front. Charming, sleepy little town. Don't plan on swimming at this beach and bring bug spray in summer. We will be back! Zero complaints"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Cozy Country Setting to relax! 15 min to Dover, DE
Cozy Country Setting to relax! 15 min to Dover, DE
Cozy tiny home with a loft, located at Bowers Beach
The price is AU$195
per night
9 July - 10 July
Cozy tiny home with a loft, located at Bowers Beach
Unique Pet-Friendly Dover Home w/ Skylight
10.0 out of 10, Exceptional, (7)
"It was well worth it. There is plenty of room for a big group. The house is clean and nice and quiet."
Unique Pet-Friendly Dover Home w/ Skylight
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
10.0 out of 10, Exceptional, (3)
"Place was newly decorated, very clean, very comfortable. It had all the amenities listed, a comfortable bed and was just very pleasant."
The price is AU$414
per night
7 July - 8 July
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Your perfect Maryland escape awaits!
Your perfect Maryland escape awaits!
Wildwood Camper De Sleeps 6-7,
2.0 star property
Wildwood Camper De Sleeps 6-7,
Guest Suite for up to 2 in a Victorian on the Chester River
10.0 out of 10, Exceptional, (1)
"The property was delightful - well appointed with all items needed and some extra for an overnight stay. The manager was responsive to issues with access to the property and resolved quickly. She also shipped us a shirt we left behind! Would highly recommend this property."
The price is AU$190
per night
26 June - 27 June
Guest Suite for up to 2 in a Victorian on the Chester River
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
9.8 out of 10, Exceptional, (21)
"Our family had a lovely stay at Brenda's property. Communication was easy and the property was delightful. Everything was immaculate and in great condition. We will hope to stay here again when we have the opportunity."
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
Be persuaded to experience this vintage cottage by the Sassa
9.0 out of 10, Wonderful, (6)
"We planned a 40th birthday get a way for a friend - three couples total stayed at this wonderful home. There was plenty of space for everyone, room to hang out and a great table to playing card games. At first, we were concerned about the shared dock - but there is more than enough room for everyone out there and what a beautiful space it is. We floated in the water each day and prepared meals each night. The kitchen is very well stocked. The house was extremely clean and the hosts are so...
Be persuaded to experience this vintage cottage by the Sassa
Don't see what you're looking for?
See all available properties in Cheswold
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.

Cheswold Holiday Home Travel Info

Other types of properties in Cheswold you may be interested in

Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1402)
"Great stay!"
The price is AU$134
per night
1 July - 2 July
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, (1002)
"Excellent staff and clean room, wish it had ice machine but everything was great!"
The price is AU$144
per night
23 June - 24 June
Microtel Inn & Suites by Wyndham Dover
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.

Everything you need to know about Cheswold holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheswold holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheswold holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cheswold holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheswold. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheswold holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheswold holiday rentals we have selected for you start as low as AU$190 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cheswold rentals

At Expedia, we put the best Cheswold holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheswold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheswold holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheswold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Wind Song Getaway on the Beach: This holiday home rental outside of Cheswold is located on the beach, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Cheswold?

While exploring the area, visit family-friendly sights like Hoppin Good Time, or get outside and enjoy nature at Wheel of Fortune. 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.

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