Woodside Vacation Rentals

Check prices for these dates

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 29 - Aug 31
Next weekend
Sep 5 - Sep 7

Vacation Rentals in Woodside

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
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
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
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!
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
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
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
Cozy cottage on the Miller farm.
Exterior

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
On the beach, sun loungers

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
Outdoor dining

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!
Smart TV

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
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
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, (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. "
$271 nightly
The price is $278
Aug 27 - Aug 28
Total with taxes and fees
Poe Themed Home Close to Beaches and 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
Guest suite in the woods with private entry
Exterior

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!
1 bedroom, iron/ironing board, WiFi, bed sheets

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."
$225 nightly
The price is $230
Sep 19 - Sep 20
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Oceanfront Milford Home w/ View & Boat Access
Game room

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!
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!
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

Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

10/10 Excellent
"Great place to stay."
Lorenzo 1-night trip
Posted 23 hours ago
Microtel Inn & Suites by Wyndham Dover

Find out more about Woodside

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 $230 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

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?

Captain's Quarters: This vacation home rental outside of Woodside is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.