Cheswold Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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.
$138 nightly
The price is $141
Nov 11 - Nov 12
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

2. 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, (5 reviews)
"Host was great"
United States
mark o.
$581 nightly
The price is $592
Nov 9 - Nov 10
Total with taxes and fees
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$110 nightly
The price is $117
Nov 9 - Nov 10
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A round window with a view of a garden, a tree, and a building in the background.

4. 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.
$349 nightly
The price is $358
Nov 15 - Nov 16
Total with taxes and fees
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
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.
$248 nightly
The price is $253
Nov 9 - Nov 10
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A beach with houses and trees.

6. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
$732 nightly
The price is $732
Nov 8 - Nov 9
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
A beach with houses and trees.

7. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
$699 nightly
The price is $716
Nov 8 - Nov 9
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a sink.

8. 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.
$451 nightly
The price is $466
Nov 7 - Nov 8
Total with taxes and fees
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
Cottage image
Cottages
Cottages

Top Cheswold Hotel Reviews

A modern lobby with a grey sofa, blue armchairs, and a small table. There are artwork on the walls and a map.
Holiday Inn Express Hotel & Suites Dover by IHG

Holiday Inn Express Hotel & Suites Dover by IHG

Holiday Inn Express Hotel & Suites Dover by IHG
Dover

10/10 Excellent

Easy and speedy check in , staff was very pleasant n welcoming, clean and cozy, I would definitely recommend and return on my next trip!!
United States
Melissa
Reviewed March 30, 2025
Holiday Inn Express Hotel & Suites Dover by IHG

Find out more about Cheswold

Everything you need to know about Cheswold vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheswold vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheswold vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheswold vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheswold. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cheswold in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cheswold rentals

At Expedia, we put the best Cheswold vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheswold rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheswold vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheswold. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.