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Woodside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Woodside vacation rentals

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

1. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$181 nightly
The price is $186
Oct 15 - Oct 16
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A bedroom with a bunk bed, a single bed, a desk, and a chair.

2. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
$203 nightly
The price is $207
Oct 26 - Oct 27
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

3. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
$248 nightly
The price is $255
Oct 15 - Oct 16
Total with taxes and fees
Mini Aruba RV/Glamping Tent
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

4. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
$536 nightly
The price is $547
Oct 15 - Oct 16
Total with taxes and fees
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A patio area with outdoor seating, string lights, and potted plants.

5. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
8.6 out of 10, Excellent, (16 reviews)
"Theme decor was awesome. Location was a quick stroll downtown. Very busy street so use a white noise app on your phone if street noise is an issue."
United States
Dee Z. B.
$268 nightly
The price is $275
Oct 11 - Oct 12
Total with taxes and fees
Poe Themed Home Close to Beaches and DE Turf
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

6. Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
10.0 out of 10, Exceptional, (3 reviews)
"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!! "
United States
Shaine L.
$219 nightly
The price is $224
Oct 11 - Oct 12
Total with taxes and fees
Cozy Unit in Milford, Delaware -Close to DE Turf
A round window with a view of a garden, a tree, and a building in the background.

7. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
$372 nightly
The price is $382
Oct 18 - Oct 19
Total with taxes and fees
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A modern living space with a dining area, sofa, and kitchen.

8. Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our family while at a lacrosse tournament. It was close to the field and very comfortable. Having two full bathrooms to get ready for the day was a treat! The property was clean and spacious. Also, the host was also extremely responsive. We will definitely return."
United States
Jill M.
$313 nightly
The price is $333
Oct 15 - Oct 16
Total with taxes and fees
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

9. Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Milford
9.2 out of 10, Wonderful, (10 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
$317 nightly
The price is $326
Oct 13 - Oct 14
Total with taxes and fees
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a sink.

10. Come stay at our beautiful 3 bedroom home located in rural Milford De.

Come stay at our beautiful 3 bedroom home located in rural Milford De.
Milford
10.0 out of 10, Exceptional, (6 reviews)
"The guys went to the race and they were very happy with the location the price and the people were very nice to deal with"
United States
debra h.
$486 nightly
The price is $501
Oct 11 - Oct 12
Total with taxes and fees
Come stay at our beautiful 3 bedroom home located in rural Milford De.
A patio with a table and chairs, an umbrella, and a covered grill.

11. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
$732 nightly
The price is $732
Oct 11 - Oct 12
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
A balcony with a view of a grassy field, a white fence, and a building with a grey roof.

12. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
$711 nightly
The price is $728
Oct 11 - Oct 12
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
Pool

13. Waterfront studio w/ pool - shopping and beaches

Waterfront studio w/ pool - shopping and beaches
Lincoln
10.0 out of 10, Exceptional, (1 review)
"Location was great for our needs. Left feeling refreshed and happy. The decor is uplifting. Beds very comfortable. Thanks for the offering!"
United States
Paula R.
$198 nightly
The price is $211
Oct 14 - Oct 15
Total with taxes and fees
Waterfront studio w/ pool - shopping and beaches
Pool

14. New 3‑BR Ranch by DE Turf & Beaches

New 3‑BR Ranch by DE Turf & Beaches
Lincoln
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful accommodations that are very comfortable. We would stay there again."
United States
Beth S.
$285 nightly
The price is $304
Oct 19 - Oct 20
Total with taxes and fees
New 3‑BR Ranch by DE Turf & Beaches
Pool

15. The Little house W/ Pool & Spa

The Little house W/ Pool & Spa
Lincoln
9.8 out of 10, Exceptional, (6 reviews)
"Host was very helpful and has great communication. Beautiful place to stay!"
United States
veronica d.
$295 nightly
The price is $314
Oct 14 - Oct 15
Total with taxes and fees
The Little house W/ Pool & Spa
A wooden cabin with a porch, a rocking chair, and a table.

16. Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, we had a very pleasant stay"
United States
andy O.
$301 nightly
The price is $310
Oct 11 - Oct 12
Total with taxes and fees
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Pool

17. Tiny house w/ Pool on water near Beaches / turf

Tiny house w/ Pool on water near Beaches / turf
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful tiny home with lavish pool in a quiet neighborhood. Loved the area, the home, and amenities provided. Although, we did not receive the code to unlock the door at check in time and host did not answer our text for about 40 minutes. Thankfully the housecleaner was there to let us in! Still a great stay. "
United States
Jessica W.
$181 nightly
The price is $192
Oct 12 - Oct 13
Total with taxes and fees
Tiny house w/ Pool on water near Beaches / turf
A modern kitchen with a large island, bar stools, and pendant lighting.

18. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
$798 nightly
The price is $815
Oct 11 - Oct 12
Total with taxes and fees
Spacious 5 Bedroom w/Pool, Patio and Theater
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

8/10 Good
"Great location. Room clean, however both beds were lumpy with apparent wear in the sleeping areas. Not very comfortable at all. Also we were on the backside of the property with spotlights shining in window. Had to keep curtains closed at all times. Experience was OKAY to GOOD."
Larry 1-night trip
Posted 4 hours 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 $211 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.

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 Silver Lake Park. 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.