Cheswold Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Cheswold

Home away from home
7.6 out of 10, Good, 5 reviews
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Captain's Quarters
9.8 out of 10, Exceptional, 67 reviews
"We stayed in Bowers for a lacrosse tournament at DE Turf Fields; I recommend it - very convenient! The house and location made it more like a vacation than a tournament weekend 🙂. Great access to the water. The property manager was very responsive and accommodating!"
Captain's Quarters
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 3 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Save an average of 15% on thousands of hotels when you're signed in
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
The price is CA $958
CA $1,406 total
includes taxes & fees
Jul 6 - Jul 7
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, 4 reviews
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Bowers Beach Vacation Rental: 2 Blocks Away!
9.0 out of 10, Wonderful, 2 reviews
"Great place for us. Appreciate the bottled water dispenser and extra water bottle. Only thing I could say that was negative was the master bed mattress was way too soft and gave my wife and I some neck soreness. All in all we really enjoyed our stay."
Bowers Beach Vacation Rental: 2 Blocks Away!
Blue Room in Delaware
8.0 out of 10, Very good, 1 review
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
Be persuaded to experience this vintage cottage by the Sassa
9.0 out of 10, Wonderful, 6 reviews
"We planned a 40th birthday get a way for a friend - three couples total stayed at this wonderful home. There was plenty of space for everyone, room to hang out and a great table to playing card games. At first, we were concerned about the shared dock - but there is more than enough room for everyone out there and what a beautiful space it is. We floated in the water each day and prepared meals each night. The kitchen is very well stocked. The house was extremely clean and the hosts are so...
Be persuaded to experience this vintage cottage by the Sassa
Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, 14 reviews
"Was the most relaxing vacation ever. The best front porch and great bay views. Loved all the spawning horseshoe crabs! Will definitely come again."
Wind Song Getaway on the Beach
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
10.0 out of 10, Exceptional, 6 reviews
"I hosted four teenage boys for a lacrosse tournament in Frederica. Fields were 10 minutes away. It was great staying in a home vs a hotel. Comfy beds. Responsive host. Accommodated our needs for adjusted check out. Big comfy couch and porches as re relaxing set up. Restaurant and food truck were amazing and had live music both nights in parking lot in front. Charming, sleepy little town. Don't plan on swimming at this beach and bring bug spray in summer. We will be back! Zero complaints"
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
10.0 out of 10, Exceptional, 1 review
"The property was delightful - well appointed with all items needed and some extra for an overnight stay. The manager was responsive to issues with access to the property and resolved quickly. She also shipped us a shirt we left behind! Would highly recommend this property."
The price is CA $93
CA $171 total
includes taxes & fees
Jun 26 - Jun 27
Guest Suite for up to 2 in a Victorian on the Chester River
Cozy Country Setting to relax! 15 min to Dover, DE
Cozy Country Setting to relax! 15 min to Dover, DE
Cozy tiny home with a loft, located at Bowers Beach
The price is CA $178
CA $205 total
includes taxes & fees
Jun 27 - Jun 28
Cozy tiny home with a loft, located at Bowers Beach
Peaceful country home away in the wilderness
10.0 out of 10, Exceptional, 12 reviews
"We enjoyed staying here. We enjoyed the farm life. Loved the chickens ! The home was very inviting and comfortable-loved the Farm Decor. Beds were comfortable, everything we needed was there for us. Great place to stay!"
Peaceful country home away in the wilderness
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks
10.0 out of 10, Exceptional, 9 reviews
"So many places to relax. The house is comfortable and so well thought out. Everything you need for a great stay."
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks
Your perfect Maryland escape awaits!
Your perfect Maryland escape awaits!
Wildwood Camper De Sleeps 6-7,
2.0 star property
Wildwood Camper De Sleeps 6-7,
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
9.8 out of 10, Exceptional, 22 reviews
"Our family had a lovely stay at Brenda's property. Communication was easy and the property was delightful. Everything was immaculate and in great condition. We will hope to stay here again when we have the opportunity."
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
10.0 out of 10, Exceptional, 4 reviews
"Great location, and beautiful property. Nicely equipped."
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
SOBO Beach House
9.6 out of 10, Exceptional, 9 reviews
"My family and stayed here while our son was participating in a LAX Tournament at DE Turf Fields. Very convenient location within 15 min of the fields. Plenty of room for my family of 5. QUIET, lots of nature around to enjoy. The house had everything we needed to cook after the games. Honestly no complaints from us except for the top floor with the bedrooms was SUPER hot about 78-80 degrees. I think the owners had just gotten a new system they were working to figure out, hopefully they can get...
SOBO Beach House
Don't see what you're looking for?
See all available properties in Cheswold
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.

Cheswold Vacation Rental Travel Info

Other types of properties in Cheswold you may be interested in

Home away from home
7.6 out of 10, Good, 5 reviews
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,413 reviews
"Good hotel .. friendly staff .. but parking is an issue.. there is no dedicated lot for the hotel guests and on weekends it’s hard finding parking.. "
The price is CA $92
CA $123 total
includes taxes & fees
Jul 1 - Jul 2
Bally's Dover Casino Resort
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, 1,005 reviews
"Everyone here has a great attitude, and the hotel was a restful stay. Good sense of privacy, but the footsteps from the room upstairs can be a bit loud. The breakfast was basic but good. 24/7 coffee is a nice perk. Great place to turn in for the night and sleep. "
The price is CA $122
CA $134 total
includes taxes & fees
Jun 25 - Jun 26
Microtel Inn & Suites by Wyndham Dover
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.

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?

Home away from home: Visitors give good reviews to this Cheswold vacation home rental, which offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Cheswold?

While exploring the area, visit family-friendly sights like Hoppin Good Time, or get outside and enjoy nature at Wheel of Fortune. 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.

Recent reviews of Cheswold properties
Expedia verified reviews