Liberty and Independence Monument, Dover Delaware USA, Dover, Delaware

Cheswold Vacation Rentals

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Our top choices for Cheswold vacation rentals

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, (23 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 CA $96
CA $176 total
includes taxes & fees
Jun 25 - Jun 26
Guest Suite for up to 2 in a Victorian on the Chester River

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 CA $235
CA $377 total
includes taxes & fees
Jun 30 - Jul 1
Mini Aruba RV/Glamping Tent

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, (3 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $127
CA $217 total
includes taxes & fees
Jun 25 - Jun 26
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
8.8 out of 10, Excellent, (5 reviews)
"Destination wedding location. Family, fun, and fellowship in this comfortable home with all the amenities! We played pool, enjoyed the central location, and used all the beds. Check in was easy and host was supportive. It met our needs and we felt right at home. "
United States
Linda K.
The price is CA $317
CA $675 total
includes taxes & fees
Jul 1 - Jul 2
Right in the center of everywhere in Dover

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 CA $378
CA $594 total
includes taxes & fees
Jun 21 - Jun 22
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Welcoming 3-bedroom house with AC in charming Milford.

Welcoming 3-bedroom house with AC in charming Milford.
Milford
10.0 out of 10, Exceptional, (2 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 CA $458
CA $706 total
includes taxes & fees
Jun 25 - Jun 26
Welcoming 3-bedroom house with AC in charming Milford.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cheswold. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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, Saulsbury Road Park 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 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.