Woodside Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Woodside

Bayfront Cottage with Spectacular Views
Terrace/patio

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (462)
"Amazing stay! The home was beautiful, cozy, and extremely well stocked. Beautiful and peaceful location. We felt very much at home. We would love to come back for another visit!"
Bayfront Cottage with Spectacular Views
Charming 3-bedroom Ranch in delightful Dover with AC
Interior

Charming 3-bedroom Ranch in delightful Dover with AC

Charming 3-bedroom Ranch in delightful Dover with AC
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Property grounds

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (130)
"Nice quiet spot, steps away from the Bay! Very beautiful!"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Cozy Beach Front Cottage Pet Friendly
On the beach, sun-loungers

Cozy Beach Front Cottage Pet Friendly

10.0 out of 10, Exceptional, (27)
"We had an amazing experience at this cottage! It was very home like an private. I hope to visit again one day!"
Cozy Beach Front Cottage Pet Friendly
Cozy cottage on the Miller farm.
Exterior

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (232)
"Awesome place. "
Cozy cottage on the Miller farm.
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, (26)
"Loved the house and location. We loved being close to a quiet beach area. The local restaurant was the best food we had on the trip. The host was easy to work with and great at communication. We would stay again! "
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
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, (4)
"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$1,261
HK$2,166 total
includes taxes & fees
14 Oct - 15 Oct
Poe Themed Home Close to Beaches and DE Turf
Grandma's Cottage Milford Delaware
Exterior

Grandma's Cottage Milford Delaware

10.0 out of 10, Exceptional, (109)
"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 Milford Delaware
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (100)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
Nirvana on the beach
Exterior

Nirvana on the beach

9.6 out of 10, Exceptional, (27)
"A great place to stay to see the horseshoe crabs at Full moon! Nicely equipped house on the perfect quiet beach. Close enough to restaurants and stores to be easy…"
Nirvana on the beach
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, (123)
"We really enjoyed our stay! The cottage was very clean, had a fully stocked kitchen, great backyard. This is a perfect spot if you want to have a quiet relaxing time at the beach. It was close to other attractions also. "
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
Secluded Beach home with amazing views.
Smart TV, fireplace

Secluded Beach home with amazing views.

10.0 out of 10, Exceptional, (44)
"Thanks for the great stay… beautiful views!"
Secluded Beach home with amazing views.
Exquisite Beachfront Cottage With Panoramic Views
Interior

Exquisite Beachfront Cottage With Panoramic Views

9.6 out of 10, Exceptional, (41)
"This beautiful cozy cottage was just what we were looking for! Exquisitely decorated. "
Exquisite Beachfront Cottage With Panoramic Views
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, (26)
"Great place to stay with a family. Very nicely decorated and clean. "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
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, (15)
"Ann is the most gracious host! And her place feels like a refuge- from everything. Wish we could have stayed longer! "
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
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)
"From the time we checked in til we checked out was a pleasure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Guest suite in the woods with private entry
Exterior

Guest suite in the woods with private entry

10.0 out of 10, Exceptional, (44)
"Short weekend stay for lax tourney for my son. Second time staying at property and always clean and relaxing. "
Guest suite in the woods with private entry
New 3‑BR Ranch by DE Turf & Beaches
Private kitchen

New 3‑BR Ranch by DE Turf & Beaches

10.0 out of 10, Exceptional, (2)
"Beautiful accommodations that are very comfortable. We would stay there again."
The price is HK$771
HK$1,836 total
includes taxes & fees
20 Oct - 21 Oct
New 3‑BR Ranch by DE Turf & Beaches
Fishermen's Catch
Exterior

Fishermen's Catch

9.4 out of 10, Exceptional, (10)
"Will definitely stay here again in the future! Thank you!"
Fishermen's Catch
Cozy Unit in Milford, Delaware -Close to DE Turf
Terrace/patio

Cozy Unit in Milford, Delaware -Close to DE Turf

10.0 out of 10, Exceptional, (2)
"Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! "
The price is HK$925
HK$1,752 total
includes taxes & fees
15 Oct - 16 Oct
Cozy Unit in Milford, Delaware -Close 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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Top Woodside Hotel Reviews

Days Inn by Wyndham Dover Downtown

Days Inn by Wyndham Dover Downtown

10/10 Excellent
"😃"
Yolanda 3-night trip
Posted 2 days ago
Days Inn by Wyndham Dover Downtown

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!

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?

Bayfront Cottage with Spectacular Views: This holiday home rental outside of Woodside is located on the beach, and has a fireplace, a patio 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.