Woodside Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Woodside

Bayfront Cottage with Spectacular Views
Terrace/patio

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (460)
"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
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Property grounds

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (128)
"Our 3rd time staying at the cottage & it was wonderful. Can’t wait to come back :)"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
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
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (99)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
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
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 ￥24,260
￥41,674 total
includes taxes & fees
Sep 27 - Sep 28
Poe Themed Home Close to Beaches and 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!
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, (24)
"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
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
Peaceful living just outside of town
Smart TV, video games, stereo

Peaceful living just outside of town

10.0 out of 10, Exceptional, (12)
"Great for what we needed!Thanks for letting us check in early!!!"
Peaceful living just outside of town
Lee's Place Brand New 2BR Townhouse w/free parking
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (28)
"It was a great option for our Lacrosse weekend!"
Lee's Place Brand New 2BR Townhouse w/free parking
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
Grandma's Cottage Milford Delaware
Exterior

Grandma's Cottage Milford Delaware

10.0 out of 10, Exceptional, (108)
"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
The Mermaid Cottage WaterFront Cottage
On the beach

The Mermaid Cottage WaterFront Cottage

9.6 out of 10, Exceptional, (180)
"Slaughter Beach is private, quiet, clean, dog friendly and so much more. The Mermaid Cottage was perfect for enjoying everything the area has to offer. We hope to return for many more vacation experiences!"
The Mermaid Cottage WaterFront Cottage
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!
Wind Song Getaway on the Beach
Interior

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (33)
"This home is beautiful! Host was responder quickly "
Wind Song Getaway on the Beach
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, (16)
"The house was terrific, well appointed, clean and comfortable. The host was very communicative and helpful. It is super convenient to the DE Turf Sports Complex. We will definitely come back. "
Hidden Gem, Relax, Water Views, Bay Breezes Elevator & Decks & Hot Tub
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!
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 ￥17,680
￥33,209 total
includes taxes & fees
Oct 8 - Oct 9
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodside Hotel Reviews

Springhill Suites By Marriott Frederica

Springhill Suites By Marriott Frederica

10/10 Excellent
"A fantastic stay with a swift check-in and a very quiet, comfortable room. The hotel is modern (2-3 years old) and well-maintained. We loved the spacious bathroom with a separate toilet, a separate shower, and two sinks. The free breakfast had a wonderful array of oatmeal toppings. The fire pit was a lovely amenity. When our shower door wouldn't open, the staff sent a repairperson who fixed it immediately."
Mi 1-night trip
Posted 2 days ago
Springhill Suites By Marriott Frederica

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Woodside?

Yes, we have vacation rentals near top attractions in Woodside, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Woodside has to offer?

Bayfront Cottage with Spectacular Views: This vacation home rental outside of Woodside is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Killens Pond State Park and Delaware State Capitol.

What are vacation rentals like in Woodside?

Vacation rentals are privately owned properties you can book for a couple days or more in Woodside. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for families.