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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Cheswold vacation rentals

Interior

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
9.8 out of 10, Exceptional, (10 reviews)
"What a wonderful place! It was very clean and is stocked with everything you could need for your stay. We thoroughly enjoyed our time there and would certainly go back whenever we’re in the area. Thank you Kara for sharing part of your home with us."
United States
Susan S.
The price is SAR 413
SAR 664 total
includes taxes & fees
6 Sep - 7 Sep
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Pool

2. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is SAR 563
SAR 926 total
includes taxes & fees
6 Sep - 7 Sep
Mini Aruba RV/Glamping Tent
Interior

3. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is SAR 220
SAR 361 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Room in Dover
Exterior

4. 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, (26 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
9 Sep - 10 Sep
Guest Suite for up to 2 in a Victorian on the Chester River
1 bedroom, desk, iron/ironing board, WiFi

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 394
SAR 874 total
includes taxes & fees
13 Sep - 14 Sep
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Interior

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 845
SAR 1,435 total
includes taxes & fees
30 Aug - 31 Aug
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Coffee/tea maker, fridge, microwave, oven

7. 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, (5 reviews)
The price is SAR 1,220
SAR 1,880 total
includes taxes & fees
31 Aug - 1 Sep
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

Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

8/10 Good
"The rooms were clean and well maintained. The surroundings were quite so could sleep without disturbances. The shower and vanity were clean and the shower worked very well. The breakfast was included and there were good choices although basic. No water bottle was provided in the nor was a drinking water fountain on the floor. Only ice machine and soda bottle dispenser machine were available."
Sunil 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Dover near Speedway

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, Woodland Beach and Saulsbury Road 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.