Woodside Vacation Rentals from CA $279: Short-Term Rentals for 2026

Q: 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.

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Our top choices for Woodside vacation rentals

A bedroom with a bunk bed, a single bed, a desk, and a chair.

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

Frederica

nahum f.

CA $272 total

includes taxes & fees

Oct 5 - Oct 6

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

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

Dover

Richard B.

CA $246 total

includes taxes & fees

Sep 29 - Sep 30

A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

3. Mini Aruba RV/Glamping Tent

Dover

Robert N.

CA $361 total

includes taxes & fees

Sep 29 - Sep 30

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

Dover

mark o.

CA $752 total

includes taxes & fees

Sep 29 - Sep 30

A modern living space with a dining area, sofa, and kitchen.

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

Milford

Jill M.

CA $466 total

includes taxes & fees

Sep 24 - Sep 25

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

Milford

Shaine L.

CA $312 total

includes taxes & fees

Oct 5 - Oct 6

A patio area with outdoor seating, string lights, and potted plants.

7. Poe Themed Home Close to Beaches and DE Turf

Milford

Dee Z. B.

CA $386 total

includes taxes & fees

Oct 5 - Oct 6

A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

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

Milford

Krista L.

CA $453 total

includes taxes & fees

Sep 23 - Sep 24

A round window with a view of a garden, a tree, and a building in the background.

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

Kitts Hummock

"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...

Alex L.

CA $538 total

includes taxes & fees

Oct 6 - Oct 7

10. Waterfront studio w/ pool - shopping and beaches

Lincoln

Paula R.

CA $279 total

includes taxes & fees

Sep 23 - Sep 24

A deck with a table and chairs, a large umbrella, and a grill.

11. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

CA $1,024 total

includes taxes & fees

Sep 23 - Sep 24

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

Lincoln

Jessica W.

CA $265 total

includes taxes & fees

Oct 5 - Oct 6

13. The Little house W/ Pool & Spa

Lincoln

veronica d.

CA $434 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a bed, a ceiling fan, a large mirror, and a door.

14. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

CA $1,071 total

includes taxes & fees

Sep 24 - Sep 25

A wooden cabin with a porch, a rocking chair, and a table.

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

Lincoln

andy O.

CA $423 total

includes taxes & fees

Sep 30 - Oct 1

A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a sink.

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

Milford

debra h.

CA $697 total

includes taxes & fees

Oct 5 - Oct 6

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

Lincoln

Beth S.

CA $426 total

includes taxes & fees

Sep 28 - Sep 29

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Top Woodside Hotel Reviews

Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

"Nice staff"

Microtel Inn & Suites by Wyndham Milford

8/10 Good

"The hotel was nice. My room was fine. I had to charge $100 extra on my card in case there was a problem with my room upon check out. I did receive a credit back promptly. The outdoor fire pit was a nice place for my family to sit at night and socialize! I had to keep one of my keys in a slot to keep the electricity working, which was different from anywhere else I have stayed. The staff was incredible!!! ☺️"

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodside vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodside vacation rentals we have selected for you start as low as CA $279 per night. Entering your travel dates in the search wizard 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 Old State House.

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.

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Check prices for these dates

Our top choices for Woodside vacation rentals

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