Woodside Vacation Rentals

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Vacation Rentals in Woodside

Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is CA $341
CA $621 total
includes taxes & fees
Jun 3 - Jun 4
Retreat Near Dover
Cozy Little Blue Cottage by the Bay
9.8 out of 10, Exceptional, (19)
"I would prefer not to."
Cozy Little Blue Cottage by the Bay
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
10.0 out of 10, Exceptional, (90)
"The house was perfect for us, tucked just behind the dunes so it was plenty private, but so close to a quiet stretch of beach that it was easy to just wander out for a walk before (and after) breakfast. The house itself is really nicely put together - cozy, clean, and well appointed with lots of convenient little touches. We would absolutely stay again!"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
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Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, (13)
"The house is clean and has everything you might need. The views are spectacular. The screened in porch is so nice to have coffee on and look at the ocean. Karen was so accommodating and easy to communicate with. We are a family of 6 and easily fit in just two of the bedrooms. The smart tvs were great. We watched a lot of movies and played chess since it’s still very chilly out. It’s incredibly relaxing being so close to the ocean and watching the sunrise. We had a wonderful stay, and will...
Wind Song Getaway on the Beach
Cozy Beach Front Cottage Pet Friendly
9.8 out of 10, Exceptional, (7)
"This was the perfect place for our family Vaca!! Very clean and well stocked with essentials. A lot of privacy is provided by the shrubbery and the beach is just a few steps away. We were 6 adults, 2 kids and 2 small dogs and we did not feel crowded at all. Loved it and definitely hope to return again. The sunrises on the beach were spectacular and there is a wildlife viewing area within walking distance for the most glorious sunsets. Definitely recommend."
Cozy Beach Front Cottage Pet Friendly
Exquisite Beachfront Cottage With Panoramic Ocean Views
9.8 out of 10, Exceptional, (13)
"Wonderful site, right on the beach. Cute, renovated cottage with all the amenities. Perfect getaway for our family of four. Big thank you to the hosts."
Exquisite Beachfront Cottage With Panoramic Ocean Views
Grandma's Cottage
10.0 out of 10, Exceptional, (78)
"Great place to relax and unwind. Our second time staying and we will be back. Wonderful proprietor"
Grandma's Cottage
The Mermaid Cottage WaterFront Cottage
9.4 out of 10, Exceptional, (155)
"The house is perfect for small families and right on the water as advertised. Both the front and back yard are fenced in with ample outdoor furniture and grill. The porch is lovely with wrap around screened in windows, we did not use the bed in this space but a nice mostly private option for those who may need it. Very mermaid themed for all mermaid lovers."
The Mermaid Cottage WaterFront Cottage
Oceanfront Milford Home w/ View & Boat Access
8.0 out of 10, Very good, (10)
"Phenomenal communication. Very clean. Decorated perfectly."
Oceanfront Milford Home w/ View & Boat Access
Guest suite in the woods with private entry
10.0 out of 10, Exceptional, (34)
"This is a really lovely property located about 15 miles south of the Delaware turf. It was quiet, clean and very comfortable. There were two queen size beds to sleep in nice size, bathroom, coffee, service in the room, as well as a decent size refrigerator, and a microwave. it is a family home there are, some comfort noises like children foot but overall, I really liked staying here and having the opportunity to get away from the typical hotel environment."
Guest suite in the woods with private entry
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
10.0 out of 10, Exceptional, (2)
"What a cute place to stay! It was quiet and peaceful and the bed was comfortable."
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Bowers Beach Vacation Rental: 2 Blocks Away!
10.0 out of 10, Exceptional, (1)
"Great place for us. Appreciate the bottled water dispenser and extra water bottle. Only thing I could say that was negative was the master bed mattress was way too soft and gave my wife and I some neck soreness. All in all we really enjoyed our stay."
Bowers Beach Vacation Rental: 2 Blocks Away!
Captain's Quarters
9.8 out of 10, Exceptional, (63)
"The property lived up yo expectations. I had been looking at it for a while to rent. My friends and I had enjoyable stay in April. Beds and furniture were comfortable. Hope to stay here again in the future."
Captain's Quarters
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, (17)
"From the booking all the way to check out was an excellent experience. The home is even better than the pictures & communication was prompt and above helpful. Everything you think you may need in a home is here. We stayed with our 2 teenage sons for a lacrosse tournament. It was nice to not be in the middle of all the chaos near the fields, but close enough to get to the boardwalk. The owner has a binder with information on local restaurants, things to do, etc. The only thing that put us off was...
-A travelers cottage - A place to rest after a busy day.
Beach Lodge: 3 Bedroom - Pet Friendly - Game Room - Great for Multi Families
9.8 out of 10, Exceptional, (65)
"The house was great! Plenty of room for us to spread out and plenty of activities to do inside and outside. Sarah was an amazing host and very accommodating. Our dogs had a blast! I would highly recommend The Slaughter Beach Lodge."
Beach Lodge: 3 Bedroom - Pet Friendly - Game Room - Great for Multi Families
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!
10.0 out of 10, Exceptional, (17)
"Beautiful home…gracious owners…spectacular views"
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
10.0 out of 10, Exceptional, (5)
"Charming 3 bedroom - nicely updated and decorated. Great location - quick walk to beach, JP's at Wharf, and only 10 minutes drive to DE Turf Complex. Great communication with owner. Can highly recommend!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Lee's Place Brand New 2BR Townhouse w/free parking
9.4 out of 10, Exceptional, (16)
"The town house is very cute and well located. The bedrooms and the kitchen are both good sizes. I can't speak to the appliances because we didn't cook, but the coffee maker worked well. Coffee was provided and some microwave popcorn and bottled water, which was nice, but there was no hand soap in two of bathrooms or paper towels. Would have been nice to at least have a little to get us started. Overall, though, I would recommend and would stay again."
Lee's Place Brand New 2BR Townhouse w/free parking
Don't see what you're looking for?
See all available properties in Woodside
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.

Woodside Vacation Rental Travel Info

Other types of properties in Woodside you may be interested in

Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is CA $341
CA $621 total
includes taxes & fees
Jun 3 - Jun 4
Retreat Near Dover
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1326)
"Check in took a while but other than that, no complaints. Love the variety of games at the casino."
The price is CA $97
CA $127 total
includes taxes & fees
Jun 3 - Jun 4
Bally's Dover Casino Resort
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, (1001)
"Elevator stopped working, mirrors dirty and hair in tub upon arrival "
The price is CA $108
CA $118 total
includes taxes & fees
May 30 - May 31
Red Roof Inn & Suites Dover Downtown
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Retreat Near Dover: This Woodside vacation home rental has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Killens Pond State Park. In the larger area, you’ll find Delaware State Capitol and Air Mobility Command Museum.

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.

Recent reviews of Woodside properties
Expedia verified reviews