Cheswold Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Cheswold vacation rentals

House (3 Bedrooms) | Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3 Mi to Dover Motor Speedway: Pet-friendly Retreat
3.0 star property
Dover
The price is ￥14,772
￥67,721 total
includes taxes & fees
Apr 23 - Apr 24
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is ￥22,279
￥48,380 total
includes taxes & fees
Apr 17 - Apr 18
Amazing Modern house with a full kitchen and parking
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
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,801
￥19,868 total
includes taxes & fees
Apr 28 - Apr 29
Guest Suite for up to 2 in a Victorian on the Chester River
3 bedrooms, WiFi, bed sheets

Welcoming 3-bedroom house with AC in charming Milford.

Welcoming 3-bedroom house with AC in charming Milford.
Milford
The price is ￥51,623
￥79,520 total
includes taxes & fees
Apr 24 - Apr 25
Welcoming 3-bedroom house with AC in charming Milford.
Interior

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is ￥63,536
￥92,445 total
includes taxes & fees
Apr 22 - Apr 23
JVA LUXURY HOUSING
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
The price is ￥27,799
￥38,899 total
includes taxes & fees
May 12 - May 13
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Fridge, microwave, oven, stovetop

Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.8 out of 10, Exceptional, (8 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
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, (19 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
The price is ￥11,119
￥29,886 total
includes taxes & fees
Apr 20 - Apr 21
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Beach

Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf

Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf
Dover
The price is ￥27,878
￥55,820 total
includes taxes & fees
Apr 17 - Apr 18
Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf
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
Dover
The price is ￥31,452
￥54,630 total
includes taxes & fees
Apr 20 - Apr 21
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
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
"The food was pretty good "
Leroy 2-night trip
Posted 3 hours ago
Bally's Dover Casino Resort

Find out more about Cheswold

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Look no further and take a look at our great range of rental properties in Cheswold!

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?

Bowers Retreat - Sleeps 10 - Steps to beach & bars! 10 Minutes to DE Turf!: This vacation home rental outside of Cheswold is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Cheswold?

While you're exploring the area, Wheel of Fortune and First State Heritage 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 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.