Cheswold Vacation Rentals

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    Upfront pricing

    We're not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Cheswold

Home away from home
Property grounds

Home away from home

8.0 out of 10, Very Good, (6)
"Really comfortable and in a great neighborhood."
Home away from home
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
Peaceful living just outside of town
Smart TV, video games, stereo

Peaceful living just outside of town

9.8 out of 10, Exceptional, (9)
"We really enjoyed our time there! The children enjoyed the playground set. We truly recommend! We are so grateful. Thank you! "
Peaceful living just outside of town
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Outdoor dining

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis
Pool

Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"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!"
Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis
Wind Song Getaway on the Beach
Interior

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (30)
"We enjoyed the home and the quiet town. The screened porch was a great place to relax and watch the tide come in and go out. "
Wind Song Getaway on the Beach
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Dining

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (25)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (16)
"The staff was great"
$118 nightly
The price is $125
Sep 2 - Sep 3
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (6)
"My family and I had the best time at the Outrange. The house is super cool. But the access to hiking, kayaking and even goats made it perfect. Ben is super good at communication. He responded to any of my questions quickly. I can't say enough about it. Just a really lovely property. "
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Fridge, microwave, oven, stovetop

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Bowers Beach Vacation Rental: 2 Blocks Away!
Beach nearby

Bowers Beach Vacation Rental: 2 Blocks Away!

9.8 out of 10, Exceptional, (8)
"The property was well kept."
Bowers Beach Vacation Rental: 2 Blocks Away!
Spacious 5 Bedroom w/Pool, Patio and Theater
Interior

Spacious 5 Bedroom w/Pool, Patio and Theater

9.8 out of 10, Exceptional, (7)
"Great house for a large family "
$719 nightly
The price is $732
Sep 4 - Sep 5
Total with taxes and fees
Spacious 5 Bedroom w/Pool, Patio and Theater
Countryside Cottage in Sassafras
Outdoor dining

Countryside Cottage in Sassafras

2.0 star property
Countryside Cottage in Sassafras
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Exterior

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (20)
"Perfect setting for our family get together. Plenty of space and beautifully decorated. Spent most of our time on the screened in porch.Beautiful sunset in the evening and lovely view of the river.Several family members used the kayaks and enjoyed the experience.Host was very helpful and went all out to make sure we had everything we needed."
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
Terrace/patio

Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf

10.0 out of 10, Exceptional, (14)
"This was a great place to stay while we were at a tournament at the DE turf sports complex. "
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Interior

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

9.8 out of 10, Exceptional, (10)
"Perfect rental for our family of 6 adults! Great location on the water with a fun restaurant just steps away. Highly recommend!!"
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Fishermen's Catch
Exterior

Fishermen's Catch

9.4 out of 10, Exceptional, (10)
"Great place, close to the beach"
Fishermen's Catch
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

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 $125 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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, Wheel of Fortune 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.