Woodside Vacation Rentals

Vacation Rentals in Woodside

Retreat Near Dover
Private kitchen
Retreat Near Dover
10.0 out of 10, Exceptional, 1 review
"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 $250
$455 total
includes taxes & fees
Jun 10 - Jun 11
Retreat Near Dover
Cozy Beach Front Cottage Pet Friendly
On the beach, sun loungers
Cozy Beach Front Cottage Pet Friendly
9.8 out of 10, Exceptional, 7 reviews
"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
The Mermaid Cottage WaterFront Cottage
On the beach
The Mermaid Cottage WaterFront Cottage
9.4 out of 10, Exceptional, 155 reviews
"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
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GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Property grounds
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
10.0 out of 10, Exceptional, 90 reviews
"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
Exquisite Beachfront Cottage With Panoramic Ocean Views
Interior
Exquisite Beachfront Cottage With Panoramic Ocean Views
9.8 out of 10, Exceptional, 13 reviews
"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
Oceanfront Milford Home w/ View & Boat Access
Game room
Oceanfront Milford Home w/ View & Boat Access
8.0 out of 10, Very Good, 10 reviews
"Phenomenal communication. Very clean. Decorated perfectly."
Oceanfront Milford Home w/ View & Boat Access
Cozy Little Blue Cottage by the Bay
Beach nearby
Cozy Little Blue Cottage by the Bay
9.8 out of 10, Exceptional, 19 reviews
"I would prefer not to."
Cozy Little Blue Cottage by the Bay
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!
Property grounds
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!
10.0 out of 10, Exceptional, 17 reviews
"Beautiful home…gracious owners…spectacular views"
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!
-A travelers cottage - A place to rest after a busy day.
TV
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, 18 reviews
"My husband, son and myself stayed for 7 nights. Walk in shower lower level worked great. Theres also a full bath upstairs. Location was quiet, but not too far from food stores and restaurants."
-A travelers cottage - A place to rest after a busy day.
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Property grounds
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
10.0 out of 10, Exceptional, 3 reviews
"Beautiful location. Very quiet and relaxing."
Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
Captain's Quarters
Fridge, microwave, oven, stovetop
Captain's Quarters
9.8 out of 10, Exceptional, 64 reviews
"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
Guest suite in the woods with private entry
Exterior
Guest suite in the woods with private entry
10.0 out of 10, Exceptional, 34 reviews
"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
Bowers Beach Vacation Rental: 2 Blocks Away!
Beach nearby
Bowers Beach Vacation Rental: 2 Blocks Away!
10.0 out of 10, Exceptional, 1 review
"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!
Grandma's Cottage
Exterior
Grandma's Cottage
10.0 out of 10, Exceptional, 79 reviews
"Grandmas Cottage looks exactly like the pictures, but is bigger inside. I have to say every inch of this cottage was immaculate. The grounds and gardens are welcoming. The outside chairs facing the lake are a great spot to read, drink your morning coffee or watch geese and ducks. Stores and restaurants easy to find. Self check-in and basic rules for check out easy to follow. Kudos to Helen & Walter for providing such a comfortable place to stay. I highly recommend and would rent again."
Grandma's Cottage
Wind Song Getaway on the Beach
Property grounds
Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, 13 reviews
"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
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf
Smart TV, fireplace, stereo, computer monitors
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
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
Interior
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
10.0 out of 10, Exceptional, 12 reviews
"We ran a Memorial Day Weekend Akc Hunt test for Retrievers in the Greenwood, DA area. Very convenient location. Clean and well stocked with coffee and essentials. Will return if they will have us."
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
Blue Room in Delaware
1 bedroom, iron/ironing board, internet
Blue Room in Delaware
8.0 out of 10, Very Good, 1 review
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Aerial view
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
10.0 out of 10, Exceptional, 5 reviews
"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!
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Fridge, microwave, oven, stovetop
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 2 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
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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

Number of vacation rentals
2
Known landmarks
Air Mobility Command Museum, Biggs Museum of American Art and The State House Museum
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Woodside you may be interested in

Retreat Near Dover
Private kitchen
Retreat Near Dover
10.0 out of 10, Exceptional, 1 review
"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 $250
$455 total
includes taxes & fees
Jun 10 - Jun 11
Retreat Near Dover
Bally's Dover Casino Resort
Front of property
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,365 reviews
"The room was very comfortable, and we enjoyed a restful night's sleep. The bathroom was large and roomy."
The price is $71
$94 total
includes taxes & fees
Jul 2 - Jul 3
Bally's Dover Casino Resort
Red Roof Inn & Suites Dover Downtown
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, 1,005 reviews
"Elevator stopped working, mirrors dirty and hair in tub upon arrival "
The price is $84
$92 total
includes taxes & fees
Jun 9 - Jun 10
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.

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 $250 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?

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

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel

5/5 Excellent
"Exceptional stay! Clean room and great service "
A verified traveler stayed at Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel
Posted 2 days ago
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel