Holiday Rentals in Cheswold

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Holiday Rentals in Cheswold

Home away from home

Dover
8.0 out of 10, Very good, (6)
"Nice place to stay for quick weekend. Close to everything."
United States
Julie
Home away from home

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
10.0 out of 10, Exceptional, (1)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (10)
"Check-in was very easy. House was clean and well supplied with everything we needed. Peaceful and quiet. Mowed and cleared trails to enjoy. "
United States
Carol B.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Wind Song Getaway on the Beach

Frederica
9.8 out of 10, Exceptional, (33)
"Was the most relaxing vacation ever. The best front porch and great bay views. Loved all the spawning horseshoe crabs! Will definitely come again."
United States
Jenny H.
Wind Song Getaway on the Beach

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (102)
"This house is a really nice hidden gem in a hidden gem town. The house is equipped with all that you need to have a great time on vacation. Bikes, beach chairs, corn hole, kids sand toys, well stocked kitchen. This place is a gem!"
United States
Walter H.
Captain's Quarters

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Frederica
9.4 out of 10, Exceptional, (3)
"We stayed over the July 4th weekend - the property is small but set up great. The screened in porch and the hot tub was awesome! The town is super friendly and welcoming. Would stay here again!"
United States
Richard D.
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Frederica
10.0 out of 10, Exceptional, (16)
"Everything was absolutely perfect. Quick and easy communication with the host gave me tremendous peace of mind. He worked with me on whatever concerns or needs I had. Highly recommend "
United States
Michael
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Frederica
10.0 out of 10, Exceptional, (11)
"Very Interesting place to stayGood time had by all"
United States
Gregory H.
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Peaceful living just outside of town

Camden
9.6 out of 10, Exceptional, (14)
"The house was very clean and the beds were extremely comfortable. "
United States
Kenneth A.
Peaceful living just outside of town

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena
9.8 out of 10, Exceptional, (22)
"Beautiful property overlooking the Sassafras river. Home and property above and beyond pictures. Renter easy to work with and accommodating "
United States
will u.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Middletown
9.4 out of 10, Exceptional, (9)
"Just like the pictures. Very clean and comfortable.Highly recommend!"
United States
Patricia Z.
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Countryside Cottage in Sassafras

2.0 star property
Galena
10.0 out of 10, Exceptional, (1)
"Very nice home. Peaceful setting."
United States
James L.
Countryside Cottage in Sassafras

Fishermen's Catch

Frederica
9.4 out of 10, Exceptional, (10)
"Great place, close to the beach"
United States
Anonymous traveller
Fishermen's Catch

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Middletown
9.2 out of 10, Wonderful, (5)
"My family and I really enjoyed staying at Kameka's property. It is very clean and upkept; you literally have everything that you need. The grocery store is within walking distance and stays open late. It is a very quiet area, no one hanging out, and I felt very secure/safe. I would definitely stay again when visiting in Delaware. ☺ 💕 "
United States
Shamika
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Be persuaded to experience this vintage cottage by the Sassa

Galena
9.2 out of 10, Wonderful, (11)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa

JVA LUXURY HOUSING

Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is €520
includes taxes & fees
21 Nov - 22 Nov
JVA LUXURY HOUSING

Camper Apt DE Sleeps 3

2.0 star property
Dover
2.0 out of 10, (1)
"The place did not appear in pictures. I could not take a shower because stuff was stored in there . The toilet was not clean . It was just a lot of junk everywhere "
United States
Tanshanicka
Camper Apt DE Sleeps 3

Saybrook Hall | Pickleball + Pool + Hot Tub

Warwick
8.0 out of 10, Very good, (1)
"Fine, well-appointed house, beautiful surroundings. Not enough hot water or water pressure. "
United States
Joe H.
Saybrook Hall | Pickleball + Pool + Hot Tub

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Frederica
10.0 out of 10, Exceptional, (27)
"Loved the house and location. We loved being close to a quiet beach area. The local restaurant was the best food we had on the trip. The host was easy to work with and great at communication. We would stay again! "
United States
Janova L.
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf

Frederica
10.0 out of 10, Exceptional, (15)
"We were there for a short amount of time but it was clean and located in a quiet neighborhood. It is located close to the beach as well. "
United States
Natalie P.
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
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

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, apart-hotels, 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 favorite 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 depends 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 €520 per night. Entering your travel dates in the search wizard you might find 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?

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 Silver Lake 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.