Woodshade Holiday Rentals

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Holiday Rentals in Woodshade

Cozy Spring House in Gorgeous Chadds Ford!

10.0 out of 10, Exceptional, (53)
"This location offers great access to Longwood Gardens and other cute spots in town. This location was super cute and very cozy. The only downsides to this spot was that the bedrooms are all in close proximity and the beds and pillows were firm. The host made sure our stay was welcome and kept good communication with us! I would recommend this location!"
The price is AU$504
includes taxes & fees
1 Dec - 2 Dec
Cozy Spring House in Gorgeous Chadds Ford!

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (54)
"We were relaxing and visiting Mt. Cuba. Wanted to stay in-town. House was adorable and location was great. Lots of nice touches to make everything comfortable (tea, extra blankets, multiple keys). Would absolutely come back!"
The price is AU$609
includes taxes & fees
3 Dec - 4 Dec
Homey Retreat in Historic Kennett Square!!

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake

Stylish Private Suite in the heart of Brandywine Valley

10.0 out of 10, Exceptional, (167)
"This property is quite simply a 10 out of 10"
The price is AU$302
includes taxes & fees
3 Dec - 4 Dec
Stylish Private Suite in the heart of Brandywine Valley

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (28)
"This house exceeded our expectations! From the pictures, we knew it would be beautiful, but once we got there it seemed so much bigger and brighter than what the pictures show. Its so light and airy and was perfect for what we came for. It was VERY clean, each bedroom came with towels and makeup wipes. You can tell the hosts put a lot of thought into this home. We went in the fall, but was still such a wonderful time walking along the quiet beach and having drinks on the patio. Would highly...
Beachfront Sunsets on the Water at Oakwood Beach

Historic Kennett Square

9.4 out of 10, Exceptional, (40)
"Cute and cozy home, Host is a great communicator. "
Historic Kennett Square

The Walton House by RPG

10.0 out of 10, Exceptional, (25)
"The house is beautiful with the perfect mix of historic charm and modern amenities. I am a light sleeper and I liked that the bedrooms seemed to have good blinds. Because it is on a major street, there was some traffic noise. I was able to drown that out with a white noise machine. The beds and pillows were all very comfortable. The only issue I had was on the day of checkout. I wasn't aware that the roads would be shut down for a half marathon. We couldn't leave at the required check-in time. I...
The Walton House by RPG

Convinient location, Remodel Apartment

10.0 out of 10, Exceptional, (9)
"Well maintained. Great management."
Convinient location, Remodel Apartment

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

A cottage on the shore of the Delaware River

9.8 out of 10, Exceptional, (59)
"The coziest house we have ever stayed at ! The host went above and beyond to have everything we could need! Would definitely recommend ! "
A cottage on the shore of the Delaware River

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is AU$796
includes taxes & fees
10 Dec - 11 Dec
Historic Chesapeake City Stay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Historic home in the heart of Main Street- walkable to shops and restaurants

10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
The price is AU$710
includes taxes & fees
10 Dec - 11 Dec
Historic home in the heart of Main Street- walkable to shops and restaurants

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (10)
"Couple little things were annoying. Overall a place/property we love. This was our third visit and plan for another."
Stunning waterfront villa with indoor pool and kids swing set and play area.

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is AU$1,006
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Super cute 3 bedroom remodeled townhouse near downtown Wilmington

8.8 out of 10, Excellent, (11)
"Amazing stay. nice quiet clean home. Accommodating for the whole family. Host was easy to connect with very helpful loved our stay ! Looking forward to booking again."
Super cute 3 bedroom remodeled townhouse near downtown Wilmington

Welcome to Woodview Estates!

8.0 out of 10, Very good, (3)
"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...
Welcome to Woodview Estates!

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
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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Other types of properties in Woodshade you may be interested in

Sonesta Select Newark Christiana Mall

3.0 star property
7.8 out of 10, Good, (1087)
"Great people "
The price is AU$169
includes taxes & fees
6 Dec - 7 Dec
Sonesta Select Newark Christiana Mall

Fairfield Inn by Marriott Kennett Square Brandywine Valley

2.5 star property
8.8 out of 10, Excellent, (1052)
"Ask for a room on the front of the hotel. There's a lot of traffic noise on the back side"
The price is AU$216
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn by Marriott Kennett Square Brandywine Valley

DoubleTree by Hilton Hotel Wilmington

4.0 star property
8.0 out of 10, Very good, (1116)
"No hot water in the shower. When I reported it, the next day it was almost lukewarm."
The price is AU$176
includes taxes & fees
22 Dec - 23 Dec
DoubleTree by Hilton Hotel Wilmington
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Woodshade?

Yes, there are holiday rentals close to the most popular sights in Woodshade, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Woodshade has to offer?

Homey Retreat in Historic Kennett Square!!: This holiday home rental outside of Woodshade offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Woodshade?

While exploring the area, visit family-friendly sights like The Patriot Ice Center, or get outside and enjoy nature at Lewden Green Park. In the wider area, you’ll find Christiana Skating Center and Christiana Mall.

What are holiday rentals like in Woodshade?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodshade. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.