A statue of soldiers with a flag, set against a brick building and trees.

Cheswold Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Cheswold vacation rentals

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

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 SAR 451
SAR 700 total
includes taxes & fees
18 Oct - 19 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

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 SAR 601
SAR 958 total
includes taxes & fees
12 Oct - 13 Oct
Mini Aruba RV/Glamping Tent
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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 SAR 255
SAR 470 total
includes taxes & fees
5 Oct - 6 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

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 SAR 897
SAR 2,053 total
includes taxes & fees
15 Oct - 16 Oct
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A bedroom with a bunk bed, a single bed, a desk, and a chair.

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 SAR 300
SAR 761 total
includes taxes & fees
15 Oct - 16 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A round window with a view of a garden, a tree, and a building in the background.

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 SAR 844
SAR 1,434 total
includes taxes & fees
18 Oct - 19 Oct
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A modern kitchen with a large island, bar stools, and pendant lighting.

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
A patio with a table and chairs, an umbrella, and a covered grill.

8. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
The price is SAR 1,577
SAR 2,748 total
includes taxes & fees
4 Oct - 5 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
A balcony with a view of a grassy field, a white fence, and a building with a grey roof.

9. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
The price is SAR 1,318
SAR 2,718 total
includes taxes & fees
15 Oct - 16 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a sink.

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 SAR 1,220
SAR 1,880 total
includes taxes & fees
3 Oct - 4 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

Sleep Inn & Suites Dover University Area

Sleep Inn & Suites Dover University Area

8/10 Good
"Room with a king bed was a good size. It was a little musty, but bed was comfortable and sheets were clean. Bathroom was clean. Shower had shampoo and conditioner installed on the wall. There was bar soap for the sink and for the shower/tub. Staff were kind and efficient. Breakfast was good - hot scrambled eggs and sausage links, waffle maker, cereal, coffee, pastries, etc."
Mary 1-night trip
Posted 11 hours ago
Sleep Inn & Suites Dover University Area

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?

Captain's Quarters: This vacation home rental outside of Cheswold is located near the beach and has a balcony, a garden, and a barbecue grill 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 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, 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 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.