Woodside Holiday Rentals

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Check prices for these dates

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept

Holiday Rentals in Woodside

Our top choices for Woodside holiday rentals

Captain's Quarters
Fridge, microwave, oven, stovetop

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
Bayfront Cottage with Spectacular Views
Terrace/patio

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
Property grounds

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
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
Smart TV

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2.0 star property
10.0 out of 10, Exceptional, (11)
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
Cozy Beach Front Cottage Pet Friendly
On the beach, sun-loungers

Cozy Beach Front Cottage Pet Friendly

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

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
Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis
Pool

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

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
Peaceful living just outside of town
Smart TV, video games, stereo

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
Lee's Place Brand New 2BR Townhouse w/free parking
Exterior

Lee's Place Brand New 2BR Townhouse w/free parking

9.6 out of 10, Exceptional, (27)
"It was a great option for our Lacrosse weekend!"
Lee's Place Brand New 2BR Townhouse w/free parking
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Dining

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!
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

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
Grandma's Cottage
Exterior

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
Nirvana on the beach
Exterior

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
Outdoor dining

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (3)
"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 HK$1,263
HK$2,169 total
includes taxes & fees
31 Aug - 1 Sept
Poe Themed Home Close to Beaches and DE Turf
Cozy cottage on the Miller farm.
Exterior

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (231)
"Awesome place. "
Cozy cottage on the Miller farm.
Secluded Beach home with amazing views.
Smart TV, fireplace

Secluded Beach home with amazing views.

10.0 out of 10, Exceptional, (41)
"Amazing location, and excellent house with all the amenities! Would definitely stay again!"
Secluded Beach home with amazing views.
Exquisite Beachfront Cottage With Panoramic Ocean Views
Interior

Exquisite Beachfront Cottage With Panoramic Ocean Views

9.6 out of 10, Exceptional, (38)
"This beautiful cozy cottage was just what we were looking for! Exquisitely decorated. "
Exquisite Beachfront Cottage With Panoramic Ocean Views
Delaware Turf Bungalow’s Sister!
Exterior

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!
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
Beach nearby

Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome

9.6 out of 10, Exceptional, (122)
"Once again a great stay in this house in it's central location. It's had a few upgrades since we last stayed which has made the kitchen even better."
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
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

Search for holiday rentals in Woodside on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodside using one of the methods below:

  • View our selection of featured holiday rentals in Woodside
  • Use the map to find apartments and other holiday homes in the Woodside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodside while they last

Look no further and take a look at our great range of rental properties in Woodside!

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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.