Cheswold Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Cheswold

Property grounds
Home away from home

Home away from home

Dover
8.0 out of 10, Very Good, (6)
"Really comfortable and in a great neighborhood."
United States
Joseph M.
Home away from home
Interior
Charming 3-bedroom Ranch in delightful Dover with AC

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
Interior
Wind Song Getaway on the Beach

Wind Song Getaway on the Beach

Frederica
9.8 out of 10, Exceptional, (33)
"Location was nice, beautiful sunrises. Plenty of room, beds were super comfy and communication with owner was wondering!"
United States
Lisa K.
Wind Song Getaway on the Beach
Fridge, microwave, oven, stovetop
Captain's Quarters

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (102)
"Great communication, the house was extremely well equipped, very short walk to the beach. Perfect place to sit & unwind."
United States
Joseph L.
Captain's Quarters
Outdoor dining
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

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

Frederica
9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
United States
Ed M.
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Interior
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE 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
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, (16)
"Great place to stay, very clean and spacious. About 20 minutes from the Dover NASCAR race which was perfect. I would absolutely recommend!"
United States
Eric F.
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Smart TV, video games, stereo
Peaceful living just outside of town

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

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

Galena
9.8 out of 10, Exceptional, (22)
"Wonderful property, well stocked, and great location. Would definitely stay here again!"
United States
Ken K.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Fridge, microwave, oven, stovetop
Luxurious and spacious townhome with all necessary amenities awaits your stay.

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

Middletown
9.4 out of 10, Exceptional, (10)
"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.
Outdoor dining
Countryside Cottage in Sassafras

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
Exterior
Fishermen's Catch

Fishermen's Catch

Frederica
9.4 out of 10, Exceptional, (10)
"It was a very enjoyable stay that gave us the time to relax that we were looking for."
United States
Brad I.
Fishermen's Catch
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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

Chestertown
10.0 out of 10, Exceptional, (10)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Dining
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

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

Middletown
9.4 out of 10, Exceptional, (6)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
United States
Linda T.
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Outdoor dining
Be persuaded to experience this vintage cottage by the Sassa

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
Private kitchen
JVA LUXURY HOUSING

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 ￥62,816
￥92,497 total
includes taxes & fees
Nov 27 - Nov 28
JVA LUXURY HOUSING
Apartment, 1 Bedroom | Interior
Camper Apt DE Sleeps 3

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
Terrace/patio
Saybrook Hall | Pickleball + Pool + Hot Tub

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

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

Frederica
10.0 out of 10, Exceptional, (27)
"Our stay was perfect!From easy check in to accommodations we couldn’t ask for anything more.The home is spacious, homey, comfortable with a fully stocked kitchen. Everything was provided right down to beach chairs, umbrella and sunscreen. Highly recommended staying here and would definitely come back!"
United States
Victoria W.
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Terrace/patio
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf

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

Frederica
10.0 out of 10, Exceptional, (15)
"This was a great place to stay while we were at a tournament at the DE turf sports complex. "
United States
Jennifer W.
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

Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"Parking was good. Room was fine Breakfast could have been a little better with more protein options. Overall good stay"
William 1-night trip
Posted 4 days ago
Red Roof Inn & Suites Dover Downtown

Find out more about Cheswold

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Frequently asked questions

Are there vacation rentals in Cheswold?

Yes, we give you a choice of vacation rentals near well known sights in Cheswold, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Cheswold has to offer?

Charming 3-bedroom Ranch in delightful Dover with AC: This vacation 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 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 larger area.

What are vacation rentals like in Cheswold?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Cheswold. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.