Cheswold Vacation Rentals

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Check prices for these dates

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Jul 15 - Jul 16
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Jul 18 - Jul 20
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Jul 25 - Jul 27

Vacation Rentals in Cheswold

Home away from home
Stroll along the serene lakeside walkway, lined with lush greenery and a sturdy metal railing.

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
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Captain's Quarters

9.8 out of 10, Exceptional, (93)
"This was a wonderful home walking distance to the beach. It was spacious and extremely comfortable. We recommend it to anyone interested in a beach vacation home. "
Captain's Quarters
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Enjoy meals in the kitchen with a central island, sink, and oven, adjacent to a dining area with a table and chairs.

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

10.0 out of 10, Exceptional, (21)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Escape to a serene cabin surrounded by lush greenery and natural beauty.

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

10.0 out of 10, Exceptional, (4)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Enjoy waterfront dining with tables and chairs on the deck overlooking the water.

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. "
The price is ￥27,127
￥74,346 total
includes taxes & fees
Jul 18 - Jul 19
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Relax in this open-plan living space with a kitchen, sofa, and large window offering a view of the outdoor pool and playground.

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

10.0 out of 10, Exceptional, (7)
"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
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

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
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Relax in this serene living space with a glass-top dining table and comfortable armchair.

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

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

9.8 out of 10, Exceptional, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Peaceful living just outside of town
Relax in this inviting living space with a sofa, armchair, and coffee table, leading to a kitchen and dining area.

Peaceful living just outside of town

9.8 out of 10, Exceptional, (7)
"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
Guest Suite for up to 2 in a Victorian on the Chester River
Stunning two-story home with a gabled roof and inviting front porch.

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

10.0 out of 10, Exceptional, (14)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is ￥9,023
￥17,378 total
includes taxes & fees
Jul 16 - Jul 17
Guest Suite for up to 2 in a Victorian on the Chester River
Peaceful country home away in the wilderness
Fully equipped kitchen with a stove, refrigerator, and ample countertop space.

Peaceful country home away in the wilderness

10.0 out of 10, Exceptional, (16)
"Kids were comfortable and well accommodated. Place is nestled back behind the pastures."
Peaceful country home away in the wilderness
Wind Song Getaway on the Beach
Enjoy a panoramic ocean view from the room's large window, with a wooden deck area perfect for dining or relaxing.

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (26)
"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
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
Relax on the covered porch with comfortable benches and picnic tables.

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

10.0 out of 10, Exceptional, (12)
"We were there for a short amount of time but it was clean and located in a quiet neighborhood. It is located close to the beach as well. "
Captain's Cottage- Walking distance to beach, 10 Mins to DE Turf
Welcome to the waterfront oasis in the serene community of Kitts Hummock Beach!
Enjoy stunning beach views from the elevated balcony of this beachfront house.

Welcome to the waterfront oasis in the serene community of Kitts Hummock Beach!

8.0 out of 10, Very Good, (2)
"This property was perfect for our family. There was plenty of room, the house was very clean, and the location gave us a quiet oasis from the hustle and bustle of the lacrosse tournament. The owner was responsive and fantastic. I think my favorite part was getting to listen to the bay noise at night while going to sleep. Extremely peaceful. Would definitely recommend and hope to stay there again when we are back in the area."
Welcome to the waterfront oasis in the serene community of Kitts Hummock Beach!
Spacious 5 Bedroom w/Pool, Patio and Theater
Stairs lead to a balcony with a view.

Spacious 5 Bedroom w/Pool, Patio and Theater

9.6 out of 10, Exceptional, (5)
"Great house for a large family "
Spacious 5 Bedroom w/Pool, Patio and Theater
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Cozy retreat with a large bed, desk, and bunk bed, perfect for families or groups.

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

10.0 out of 10, Exceptional, (12)
"Place was newly decorated, very clean, very comfortable. It had all the amenities listed, a comfortable bed and was just very pleasant."
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Fishermen's Catch
Enjoy elevated outdoor space with a balcony and stairs leading to the upper level.

Fishermen's Catch

9.4 out of 10, Exceptional, (9)
"Great place, close to the beach"
Fishermen's Catch
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.
Kitchen features a stainless steel range hood, black oven, and a refrigerator, along with a coffee maker and microwave.

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

10.0 out of 10, Exceptional, (4)
"Best part was it was super close to the DE Turf for our LAX tourney! Nice home, very comfortable, clean, easy to get to and very accommodating host. "
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

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

9.6 out of 10, Exceptional, (17)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
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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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.