Woodside Vacation Rentals

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

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 24 - Oct 26
In two weeks
Oct 31 - Nov 2

Vacation Rentals in Woodside

Interior
Charming 3-bedroom Ranch in delightful Dover with AC
Charming 3-bedroom Ranch in delightful Dover with AC
Charming 3-bedroom Ranch in delightful Dover with AC
Terrace/patio
Bayfront Cottage with Spectacular Views
Bayfront Cottage with Spectacular Views
10.0 out of 10, Exceptional, (463)
"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!"
United States
Patricia P.
Bayfront Cottage with Spectacular Views
Fridge, microwave, oven, stovetop
Captain's Quarters
Captain's Quarters
9.8 out of 10, Exceptional, (101)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
United States
Criselle A.
Captain's Quarters
Property grounds
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
10.0 out of 10, Exceptional, (130)
"This is a must stay property. The location is perfect and the house is fantastic. The hosts are so thoughtful and considerate. You cannot go wrong staying here. "
United States
Kelly E.
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Exterior
Cozy cottage on the Miller farm.
Cozy cottage on the Miller farm.
10.0 out of 10, Exceptional, (234)
"We’ve stayed here several timesWe always feel welcome and the cottage is perfect!!"
United States
Ron F.
Cozy cottage on the Miller farm.
On the beach, sun loungers
Cozy Beach Front Cottage Pet Friendly
Cozy Beach Front Cottage Pet Friendly
10.0 out of 10, Exceptional, (28)
"We had an amazing experience at this cottage! It was very home like an private. I hope to visit again one day!"
United States
Brittney P.
Cozy Beach Front Cottage Pet Friendly
Dining
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
10.0 out of 10, Exceptional, (27)
"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! "
United States
Janova L.
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Exterior
Grandma's Cottage Milford Delaware
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. "
United States
Robyn
Grandma's Cottage Milford Delaware
Exterior
Nirvana on the beach
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…"
United States
Tina F.
Nirvana on the beach
Outdoor dining
Poe Themed Home Close to Beaches and DE Turf
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. "
United States
Linda I.
$271 nightly
The price is $278
Oct 19 - Oct 20
Total with taxes and fees
Poe Themed Home Close to Beaches and DE Turf
Smart TV, fireplace
Secluded Beach home with amazing views.
Secluded Beach home with amazing views.
10.0 out of 10, Exceptional, (44)
"Thanks for the great stay… beautiful views!"
United States
Kathryn M.
Secluded Beach home with amazing views.
Interior
Exquisite Beachfront Cottage With Panoramic Views
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. "
United States
suzanne s.
Exquisite Beachfront Cottage With Panoramic Views
Beach nearby
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
9.6 out of 10, Exceptional, (124)
"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. "
United States
Kim Y.
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome
Property grounds
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
9.8 out of 10, Exceptional, (27)
"Great place to stay with a family. Very nicely decorated and clean. "
United States
Meg E.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Exterior
Delaware Turf Bungalow’s Sister!
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...
United States
Christina T.
Delaware Turf Bungalow’s Sister!
1 bedroom, bed sheets
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
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."
United States
sharon P.
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Smart TV
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
2.0 star property
10.0 out of 10, Exceptional, (15)
"This was a great house. Beautiful, spacious, and so quiet. Perfect for families. "
United States
Tiffany H.
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
Exterior
Guest suite in the woods with private entry
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. "
United States
Scott M.
Guest suite in the woods with private entry
Private kitchen
New 3‑BR Ranch by DE Turf & Beaches
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."
United States
Beth S.
$225 nightly
The price is $240
Oct 20 - Oct 21
Total with taxes and fees
New 3‑BR Ranch by DE Turf & Beaches
Smart TV, video games, stereo
Peaceful living just outside of town
Peaceful living just outside of town
9.6 out of 10, Exceptional, (13)
"The house was very clean and the beds were extremely comfortable. "
United States
Kenneth A.
Peaceful living just outside of town
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"The room was clean,spacious and the bed was comfortable."
Edward 1-night trip
Posted 1 day ago
Bally's Dover Casino Resort

Find out more about Woodside

Everything you need to know about Woodside vacation rentals

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

Woodside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $240 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodside rentals

At Expedia, we put the best Woodside vacation 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 vacation.

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.

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.