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Top Holiday Rentals in Woodside

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

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

9.8 out of 10, Exceptional, (23)
"Property was fantastic. Quit and peacful. Everything that you need and very clean. "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (457)
"Well stocked house with everything you need for an amazing vacation."
Bayfront Cottage with Spectacular Views

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (125)
"Our 3rd time staying at the cottage & it was wonderful. Can’t wait to come back :)"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

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!

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

Grandma's Cottage

10.0 out of 10, Exceptional, (107)
"Born and raised in this area. Just back to visit friends and family. Staying at grandmas cottage felt like just that. Thanks. "
Grandma's Cottage

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

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (229)
"Awesome place. "
Cozy cottage on the Miller farm.

Cozy Beach Front Cottage Pet Friendly w/no pet fees

10.0 out of 10, Exceptional, (27)
"Great stay for a couple. Cozy home, quiet neighborhood, kitchen had all we needed as we brought food to heat and eat. We went birding at a bunch of parks. The beach was pretty private only a handful of people walking, no loud kids, really relaxing. "
Cozy Beach Front Cottage Pet Friendly w/no pet fees

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

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2.0 star property
10.0 out of 10, Exceptional, (10)
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Hidden Gem, Relax, Water Views, Bay Breezes Elevator & Decks & Hot Tub

10.0 out of 10, Exceptional, (15)
"We had a great stay and our hosts were great. The house is large, comfortable and perfect for families. I look forward to staying again next summer"
Hidden Gem, Relax, Water Views, Bay Breezes Elevator & Decks & Hot Tub

Nirvana on the beach

9.6 out of 10, Exceptional, (26)
"Nicely maintained, peaceful area. "
Nirvana on the beach

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (2)
"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "
The price is £212
includes taxes & fees
27 Aug - 28 Aug
Poe Themed Home Close to Beaches and DE Turf

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

Guest suite in the woods with private entry

10.0 out of 10, Exceptional, (42)
"Great location and very clean! Would stay again"
Guest suite in the woods with private entry

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

10.0 out of 10, Exceptional, (14)
"Place was newly decorated, very clean, very comfortable. It had all the amenities listed, a comfortable bed and was just very pleasant."
The price is £174
includes taxes & fees
19 Sept - 20 Sept
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Oceanfront Milford Home w/ View & Boat Access

8.0 out of 10, Very good, (17)
"It was a great location. The family enjoyed it, so beautiful"
Oceanfront Milford Home w/ View & Boat Access

Delaware Turf Bungalow’s Sister!

10.0 out of 10, Exceptional, (1)
"This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was...
Delaware Turf Bungalow’s Sister!
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 Woodside Hotel Reviews

Find out more about Woodside

Find out more about Woodside

Everything you need to know about Woodside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Woodside holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodside holiday rentals we have selected for you start as low as £174 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodside rentals

At Expedia, we put the best Woodside holiday 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 Woodside 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 Woodside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Captain's Quarters: This holiday home rental outside of Woodside is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 DE Turf Sports Complex. In the wider area, you’ll find Killens Pond State Park 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.