Woodside Holiday Rentals

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Holiday Rentals in Woodside

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (438)
"We chose Glenmor Cottage as a quiet and peaceful place to celebrate our 58th anniversary and enjoy a winter visit to the shore. The home is beautifully decorated and cozy. Hope to return when the beach walk is a little warmer."
Bayfront Cottage with Spectacular Views

Captain's Quarters

9.8 out of 10, Exceptional, (84)
"This place was large enough to accommodate my family size of 10. There was plenty of room to spread around and not to mention, the house was fully stocked with anything and everything you could need. Sean communicates quickly and is very attentive to details. Thank you Sean."
Captain's Quarters

Exquisite Beachfront Cottage With Panoramic Ocean Views

9.4 out of 10, Exceptional, (26)
"This property was just what we needed to cap our summer. It was nicely decorated and comfortable. Being close to the water and listening to the waves was so relaxing and refreshing. We would definitely consider this property again when we travel this way. Thank you! "
Exquisite Beachfront Cottage With Panoramic Ocean Views

Secluded Beach home with amazing views.

10.0 out of 10, Exceptional, (23)
"Beautiful property with everything you can need. Right on a secluded beach. Owner was very responsive. Fast internet allowed two people to work remotely at the same time. Nothing bad to say about this place, it's a gem!"
Secluded Beach home with amazing views.

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.6 out of 10, Exceptional, (5)
"The owners made sure the driveway was shoveled and left us a seashell!"
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

The Mermaid Cottage WaterFront Cottage

9.6 out of 10, Exceptional, (171)
"We were in the area to visit family and always enjoy the Slaughter Beach for its quiet natural beauty. The Mermaid Cottage was clean, comfortable, and equipped with everything we needed. We will definitely be back!"
The Mermaid Cottage WaterFront Cottage

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (25)
"This is a beautiful beach house, right on the water. Lots of amenities and upgrades. We loved the screened porch and upstairs deck. We were fine with the spiral stairs but they may be potentially challenging for some guests. The area is a little isolated and the beach was quiet in mid-October, which was perfect for us! I highly recommend this property."
Wind Song Getaway on the Beach

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

10.0 out of 10, Exceptional, (9)
"Everything was absolutely perfect. Quick and easy communication with the host gave me tremendous peace of mind. He worked with me on whatever concerns or needs I had. Highly recommend "
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

The price is AU$611
includes taxes & fees
28 Feb - 1 Mar
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

Nirvana on the beach

9.4 out of 10, Exceptional, (18)
"We had a great time here. The house was absolutely lovely! The only issue we had was that I did not check the tides before going and we were surprised by the lack of use of the ocean during low tide. However it was still nice to walk and look for shells during low tide."
Nirvana on the beach

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (104)
"We visited over Thanksgiving and the owners bent over backwards to see that we had everything we needed to prepare our Thanksgiving dinner. The house was spotless with very comfortable beds. We will be back!"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

Guest suite in the woods with private entry

10.0 out of 10, Exceptional, (38)
"Rather than staying at a noisy hotel, we opted to go with the VRBO while at a lax tourney at the DE turf. The house is located in a quiet area. We ventured into surrounding towns for local restaurants and shopping. (It does take 12-15 min to get anywhere). The accommodations were comfortable and my daughter and I had our own sleeping areas. "
Guest suite in the woods with private entry

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

10.0 out of 10, Exceptional, (5)
"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

Cozy House, in the Historic Bowers Beach. Pet Friendly and Quiet.

10.0 out of 10, Exceptional, (3)
"A nice place to stay with everything we needed to cook an early Thanksgiving dinner for our family living from Felton. Grand kids loved the game room and the neighbors are friendly and quiet.The beach is really nice to walk off season and the full moon rising over the bay was beautiful Joseph made sure we had everything we needed and checked to make sure we were happy with the stay."
The price is AU$478
includes taxes & fees
9 Mar - 10 Mar
Cozy House, in the Historic Bowers Beach. Pet Friendly and Quiet.

Spacious 5 Bedroom w/Pool, Patio and Theater

9.6 out of 10, Exceptional, (4)
"The house had everything for our family’s stay. It was perfect even on the rainy days."
The price is AU$956
includes taxes & fees
20 Feb - 21 Feb
Spacious 5 Bedroom w/Pool, Patio and Theater

Cozy tiny home with a loft, located at Bowers Beach

8.8 out of 10, Excellent, (3)
"Very sweet cottage. Clean with beach decor in every room. The neighborhood is clean & safe to take walks. Had seafood dinner at JP's Wharf & the crab cakes were yummy! Was a short walk down the street. . "
The price is AU$249
includes taxes & fees
19 Feb - 20 Feb
Cozy tiny home with a loft, located at Bowers Beach

Oceanfront Milford Home w/ View & Boat Access

8.2 out of 10, Very good, (13)
"The house was just as described and right on the water which was perfect for us. The street was extremely quiet and off the beaten path. The only issue we had was the cleanliness and some electrical issues. "
Oceanfront Milford Home w/ View & Boat Access

SOBO Beach House

9.6 out of 10, Exceptional, (12)
"We had a great stay for a lacrosse tournament we were in town for and would stay again in the future. The house had everything we needed for our stay. Sierra was great to work with. The only down side to the stay was that we did not feel the beach/bay was swimmable, but still enjoyed our walks on the beach and searching for shells."
SOBO Beach House

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

10.0 out of 10, Exceptional, (17)
"This was a last minute booking for New Years with my family. From the onset, all communication with Scott was prompt and professional. The property was beautiful and clean while also being close to eateries and groceries if you want to cook/bbq. Will definitely return in the future for a longer stay. "
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
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 Woodside you may be interested in

Bally's Dover Casino Resort

4.0 star property
8.8 out of 10, Excellent, (2261)
"The parking was in walking distance."
The price is AU$138
includes taxes & fees
20 Feb - 21 Feb
Bally's Dover Casino Resort

Microtel Inn & Suites by Wyndham Dover

2.0 star property
8.0 out of 10, Very good, (1001)
"The receptionist is welcoming. The room is nice and clean. "
The price is AU$131
includes taxes & fees
19 Feb - 20 Feb
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Milford

2.5 star property
8.8 out of 10, Excellent, (516)
"Is an easy place to stay"
The price is AU$132
includes taxes & fees
18 Feb - 19 Feb
Microtel Inn & Suites by Wyndham Milford
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.

Frequently asked questions

Can I find a holiday rental in Woodside?

Yes, there are holiday rentals close to the most popular sights in Woodside, 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 Woodside has to offer?

Secluded Beach home with amazing views. : This holiday home rental outside of Woodside is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease 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 Woodside?

While exploring the area, visit family-friendly sights like Delaware State Fairgrounds, or get outside and enjoy nature at Killens Pond State Park. In the wider area, you’ll find Blue Hen Mall and Delaware State Capitol.

What are holiday rentals like in Woodside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodside. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.