
When snow is in the forecast, planning a beach trip might not be high on your priority list. But, if you’re planning on spending your summer vacation with your toes in the sand, you’re going to need to start looking and booking now.
We’ve broken down the three summer holiday weekends in some of the key traveling areas, and what prices you can expect in 2020. If there’s one thing we can be sure of, it’s that the prices will only continue to rise throughout the year.
So, think of the beach sunrises and warm nights on the boardwalk, and get to booking!

Virginia Beach
Est. 200 miles, 3 hours from Northern Virginia
Memorial Day
You might be wondering why you should stay in-state for your Memorial Day beach trip, but if you’re a country music fan, it should be a no-brainer. Virginia Beach’s annual Patriotic Festival falls over the holiday weekend, with acts lined up such as John Pardi, Dan + Shay and Dierks Bentley. Don’t miss your chance to enjoy live tunes, raise a glass and kick back and relax. Starting on Friday, May 22 through Monday, May 25, Airbnbs in Virginia Beach are starting at $128 a night for a group of four individuals and swing up to $555 a night.
What Each Price Will Get You
The $128 a night stay, which would total $556 (including service fees, cleaning fees and occupancy taxes and fees) for the weekend, is in the Classic Beach Cottage, an entire home to yourself that can sleep up to seven guests. It is inland (exact location not available), but 100% of guests gave the location a five-star rating. Airbnb deems the opening on Memorial Day weekend as a “rare find,” and those interested should book soon—all weekends in June and July except two are already booked, as are the entirety of August and September.
The $555 a night stay, which would total $2,277 (including service fees, cleaning fees and occupancy taxes and fees) for the weekend, is Sea Dancer, a full townhouse that can sleep up to 10 guests. Although the home is not steps off the sand, the host describes the location as “close to the action of the boardwalk, nightlife, restaurants and beach, yet it sits back far enough to get away from it all.” Airbnb also deems this location as a “rare find” and even those who might be looking for another weekend should act fast—May and June are the only two months left with stays available for more than one day.
Fourth of July
Get out your stars and stripes and plan your Fourth of July trip now. Whether you’re traveling with the kids, hosting a college reunion or just looking for a change of scenery for the national holiday, Virginia Beach is ready to celebrate with you. If you book now, you’ll ensure that you won’t miss the annual Live! On Atlantic’s Stars and Stripes Explosion, where fireworks will light up the sky. Because really, what’s a holiday without a great show? Starting on Friday, July 3 through Sunday, July 5, Airbnbs in Virginia Beach are starting at $90 a night for a group of four, and ranging up to over $1,000 a night.
What Each Price Will Get You
For $90 a night, up to four guests can stay in the Camper at the Cape. Yes, there is a full 2019 Jayco Camper to rent in a wooded spot near Great Neck Creek. The downside? It’s quite a long way from the beach (based on location estimation). But, your weekend grand total would be $274 (including service fees, cleaning fees and occupancy taxes and fees) and that’s tough to beat. Plus, the camper is not yet booked for a majority of the summer, meaning you could head right back after a great stay over the holiday.
A $1,100 a night stay is quite the contrast at a full home with six bedrooms that can sleep up to 14 guests. Located four blocks from the beach, guests can ride one of the eight provided beach bikes or walk to local coffee shops, restaurants, oceanfront activities and the boardwalk. The home is also not yet booked for a majority of the summer, so you have time to coordinate with your friends and family on what weekend works best for all (potentially) 14 of you, but this property, as well as other houses of this size, could fill up quickly. The weekend total comes to $3,068 (including service fees, cleaning fees and occupancy taxes and fees).
Labor Day
Thinking of the final days of summer nearly eight months before they arrive shouldn’t make you feel as if the summer will fly by, but it will give you something to look forward to in the warmer months to come. Over Labor Day at Virginia Beach, there’s two can’t-miss events that will help you round out the summer: the Chartway Federal Credit Union American Music Festival, which features live rock jazz, country, R&B and more right on the sand at the Virginia Beach oceanfront, and the Rock ‘n’ Roll Half Marathon, where dozens of runners will take the starting line for 13.1 miles and celebrate finishing at the Toyota Rock ‘n’ Roll Concert Series. Stays for the weekend (starting on Friday, Sept. 4 through Monday, Sept. 7) in Airbnbs range from $175 a night to $1,553 a night, and could make for a great way to toast to another summer in the books.
What Each Price Will Get You
A $175-a-night stay at the 300 feet from Atlantic Ocean: Cozy Guest Suite will give guests two bedrooms for up to four guests, and a first-floor view of an oceanfront home in Virginia Beach. Of course, the main draw is the proximity to the beach, and guests can walk right out to a sand pathway leading straight to the ocean. Perfect for those looking to spend as much time on the sand as possible, with a total cost for the weekend of $672 (including service fees, cleaning fees and occupancy taxes and fees).
For a truly special stay over Labor Day weekend, book the Amazing Home in Tropical Inspired Beach Setting in Virginia Beach. The purple-and-blue cottage known as “Caroline” by the hosts is a two-story home of 2,600 feet and can sleep more than 16 guests in the four bedrooms. Located on 34th Street, the home is a three-minute walk to the shore and easily accessible to local restaurants, entertainment and more. Can’t book this one? Find one of the other 17 in the tropical-inspired theme across the city. The total weekend cost comes to $6,235 (including service fees, cleaning fees and occupancy taxes and fees).

Cape May, New Jersey
Est. 200 miles, 4.5 hours from Northern Virginia
Memorial Day
If going north for the summer is more your speed for Memorial Day weekend, we aren’t going to fault you. But to all Cape May, New Jersey, fans: Airbnb has been experiencing high volumes of interested bookers for months, including over 150 who have viewed during the same holiday dates below. So, book now or never. Since there’s quite a difference in prices to stay, find three tiers below, with a base of $95 per night to $1,800 (including service fees, cleaning fees and occupancy taxes and fees), and know there is a range in the middle, but many may book quickly prior to the summer season.
What Each Price Will Get You
If the $95-a-night stay sounds like a steal, you would be right. This Cozy Villas Home near the bay/Cape May is known for being sparkling clean, operated by an Airbnb superhost and houses up to six guests. Other perks? It has two bedrooms, one bathroom and is dog-friendly. The location is walkable to the beaches of Delaware Bay, local playgrounds, restaurants and ice cream shops, mini golf courses and the Cox Hall Creek Wildlife Refuge. If you’re bringing the kids and dogs along, the fenced-in backyard is a plus, as is the 10-minute trip to both Cape May and Wildwood. Total for the weekend is $493 (including service fees, cleaning fees and occupancy taxes and fees) and is a “rare find” for a holiday weekend.
For the mid-range traveler looking to book Airbnbs, $635 a night is just a little higher than a handful of locations still available for Memorial Day weekend. The Brand New Construction Cape May Marina District property can host up to 10 guests in four bedrooms, with six beds and three and a half bathrooms. Because the house is newly listed on the site, it has yet to be booked for its first season, and Memorial Day is still open wide (as well as other summer holidays!). One thing to note about the location is that it is located nearest to the Cape May Marina (north of the shore), so it is not a stone’s throw from the beach but still offers panoramic views of the Cape May Harbor and a peaceful place to get in that much-needed vacation. Total for the weekend is $1,956 (including service fees, cleaning fees and occupancy taxes and fees).
With Cape May’s rich history, it’s not surprising that many of the Airbnb properties are historic homes that have been modernized or renovated, and are now rented out to visitors of the vacation-worthy area. Queen Ann’s nine-bedroom Cape May House is no exception, as an 1882 classic Victorian home just three blocks away from the beach. The home sleeps up to 23 people in nine bedrooms, and has 13 beds, three and a half bathrooms and parking for up to five vehicles. The good news? The home is still available for rent over Memorial Day weekend and most of June, but (bad news) is booked for the entirety of July and most of August. Total for the weekend would be $4,887 (including service fees, cleaning fees and occupancy taxes and fees), but if you up your stay to one week, you get a 10% discount.
Fourth of July
If you’re planning to spend your Fourth of July in Cape May with the family, you won’t want to miss out on the fireworks and holiday parade. That’s right. All of your favorite festivities will be celebrated in the city while you enjoy a nice weekend away at the beach. When researched, Airbnb cited that 175 people were already looking at the same days to book local properties, and 132 places to stay were available. When booking in January, prices range from $175 for two guests (plus a dog or two) to $3,000 per night for more than 16 guests. Considering the range, find three tiers below for rentable spaces in Cape May for Independence Day.
What Each Price Will Get You
For $175 per night and two guests, the Cape May Cottage gives you space all to yourself and is north of West Cape May. Marketed as great for couples, solo travelers and four-legged friends the one-bedroom and one-bathroom location is a five-minute ride to the beach by car or a 10-minute ride by bicycle. If you’re not into staying right on the beach, this nature-heavy area is calm, relaxing and offers sightings of local horses, bald eagles and migrating birds, and is walking distance to local nature trails, small shops and other activities. The property is booked for Memorial Day and for several weeks in the summer, but is currently still available for Fourth of July weekend. The total would be $436 for three days (July 3 to 5), and if you want to be the lucky one to claim it, you’ll want to book before the other people who, according to Airbnb, “have their eyes on it,” beat you to it.
For the mid-range traveler with up to six guests the Newly Renovated, Three Bedroom, Steps Away from Sunset Bay property is $450 a night and gives guests access to the entire home. The location is just west of Wildwood Crest (north of Cape May), but is a short drive to the beach and a quick trip to the southern tip of the city. There are three bedrooms, three beds and one bathroom, as well as a backyard, outdoor shower and available parking. It is currently available for Memorial Day weekend and Fourth of July weekend, but is booked solid for most of July and all of August.
For the highest tier, The Sea Gypsy Bed and Breakfast ($3,000) offers three guest buildings in close proximity that each offer different accommodations. One of the buildings located on Magnolia Avenue is a Queen Anne-style Victorian home with a large, second-floor, wrap-around porch with a hot tub. The “arts and crafts-style” bungalow features seven suites on Poplar Avenue, and the third is the Carriage House, which includes apartment-style suites and a grass parking lot nearby. This property is located in Wildwood, but is one of the largest places to stay for families, friends and more. The buildings have been restored and sit two and half blocks from the Wildwood Boardwalk and beach. Cape May is a short 10-mile drive south and the entire area offers restaurants, pubs, bars, live entertainment and more. For more information on how room rental can break down (or how your entire family can stay), please visit the listing. Total for the weekend would be $7,472 (including service fees, cleaning fees and occupancy taxes and fees).
Labor Day
Wrapping up your summer on the sandy beaches of Cape May doesn’t sound so bad, except for that it’s just under eight months away from now. But don’t let the amount of flips in your calendar deter you from booking your vacation space sooner rather than later. Labor Day has been filled in some properties but most are still available, unlike Memorial Day and the Fourth of July. So, ranging from $150 per night for an entire home and up to five guests, to $2,167 per night in a 16-plus guest home, here are three examples (and available properties) you can book in Cape May for Labor Day.
What Each Price Will Get You
Located in the heart of Cape May, this “rare find,” according to Airbnb, is booked solid for the entire summer … except Labor Day weekend! At $150 a night, this place is a steal with one bedroom, three beds and one bathroom, and just a short walk from the beach or downtown. The historic Baronet Mansion was built in 1870 but has since been updated with new bedroom accommodations (such as a memory foam mattress and a sleeper sofa). Total for the weekend would be $685 (including service fees, cleaning fees and occupancy taxes and fees), a fraction of most other rentals of its size and location, and could be booked any minute now … so what are you waiting for?
For $1,550 a night, up to 22 friends, family and visitors alike can say at The Ocean Victorian, a house with eight bedrooms, 10 beds and seven and a half bathrooms. This historic home is located one block from the Washington Street Mall shops and restaurants and boasts a spacious kitchen, game room, televisions in every bedroom and street parking for up to five vehicles. Plus, get ocean views from both decks of the house and be a short distance from the beach for the entire duration of your trip. Unfortunately, this home is already booked for most of the season, but there is still availability over Labor Day, as well as early May and June. The weekend total would be $6,226 (including service fees, cleaning fees and occupancy taxes and fees).
For $2,167 per night, the Beachfront 4-feet, Heated pool, 20-person, Jacuzzi property has all that and more. Six bedrooms, five bathrooms, a private heated pool, Jacuzzi, televisions in every room, a master suite with a wrap-around terrace, and as soon as you step off the porch … your toes are in the sand. The property can sleep up to 22 people, making it a great location for those looking for a fun space in a great location, that can sleep an entire family (and extra guests too). The location is not yet booked for Memorial Day, Fourth of July or Labor Day weekend, but it’s opening could give you the perfect excuse for that full-family getaway you’ve been waiting for. Total for the weekend would be $9,028 (including service fees, cleaning fees and occupancy taxes and fees).

Outer Banks
Est. 300 miles, 6 hours from Northern Virginia
Memorial Day
The closest summer holiday is just over four months away, but you can already tell you’re getting antsy for summer to come closer … and to hopefully have a relaxing day off from work. Having that extra day gives you the chance to travel a little farther if you’re up for it, and the Outer Banks are ready to welcome you with open arms. In the small strip on the North Carolina coast, Airbnbs for Memorial Day weekend are ranging from $85 a night to $750 a night, depending on how many guests you’re gathering. So, get those nearly 360-degree views of the water and enjoy your time away from home.
What Each Price Will Get You
For $85 a night with two guests, this superhost location named Ocean Views with Hot Tub is located 200 yards from the ocean and nestled in the small village of Rodanthe. It should be noted that it is only the private room, a shared bathroom and a private access to the porch, but does offer hot tub access, a peaceful hammock outdoors and that oceanfront location you’re looking for in terms of convenience and as an escape to serenity. For the total price of $350 (including service fees, cleaning fees and occupancy taxes and fees) over a holiday weekend, Airbnb has this as a “rare find.”
For $750 a night, you can rent an entire home for up to nine guests. This semi-oceanfront property has four bedrooms and four bathrooms, and is also operated by a Airbnb superhost. Here’s the rundown: The home has a two-tier deck with ocean views, is steps away from the sand and boasts great surfing and fishing in the area. The interior of the home has been completely remodeled and, to top it off, is pet friendly. Total for the weekend adds up to $3,087 (including service fees, cleaning fees and occupancy taxes and fees).
Fourth of July
All right friends, it’s January and you need to know that there are very few places left for the Fourth of July on the island. Six months in advance for a two-person stay gives you only 26 places to choose from, and a group of four gives you a grand total of nine places to stay. But don’t fret! Ranging from $175 a night for a private room and bathroom to a $650 per night stay in entire townhouse, you still have time. Just probably not much.
What Each Price Will Get You
For $175 per night two-person stay, the Sound Front Suite #1 with King Bed boasts a low price, a superhost and a location just a few steps away from the Pamlico Sound. Guests have access to the lower level of the home and can either rent out all three rooms (increasing the guest count to six people), or their own private space. There is a small kitchenette, two cruising bikes, beach chairs, an outdoor shower and access to the expansive deck and pool area. Total cost wrapped up for the weekend is $477 (including service fees, cleaning fees and occupancy taxes and fees).
For $650 a night and up to 10 guests, The Turtle Club offers an entire townhouse to yourself, with four bedrooms, seven beds and two-and-half baths. The superhost-operated property has been rated five stars for location by every guest, as a cozy retreat tucked away in the Village of Avon, according to the posting. Guests have access to two large, covered decks in the front and the back of the house, access to the canal, an on-site (although shared) pool and a boat launch. There are long docks for relaxing, fishing, crabbing and docking, as well as a fully stocked kitchen. The total for the weekend comes out to $1,750, (including service fees, cleaning fees and occupancy taxes and fees) but if you have your eyes on it, move fast. Airbnb says over 30 other people have checked out the home for the same dates, just in the past week.
Labor Day
Take a long weekend over Labor Day and you’ll get the best chance to wrap up your summer with relaxation on the shore. Airbnbs are more available thus far for the late-summer holiday weekend, but beware, they could book fast. Ranging in price from around $150 per night to over $1,000, your trip can skew from a cheap beach getaway to a weekend of luxury. And if you’re looking for live entertainment (other than local music and trying out restaurants), the WRV Outer Banks Pro Surf Contest will be held in Nags Head. It’s known as one of the main surfing contests on the East Coast and could offer one-of-a-kind shows depending on what world-class surfers happen to attend. Now, let’s find a place to kick off your flip-flops.
What Each Price Will Get You
For $146 a night, the Stones Throw, Downstairs, nearly on the beach property can accommodate up to four guests with two bedrooms. The location is the biggest seller here, being in a quiet location within walking distance of the ocean, local restaurants and shops, as well as a tackle shop for fishers and a putt-putt course for the kids. You can feel the sand in your toes as soon as you walk to the door and let the sounds of the ocean lull you to sleep for the entire stress-free weekend. The total for the weekend, from Friday, Sept. 4 to Monday, Sept. comes out to $654 (including service fees, cleaning fees and occupancy taxes and fees).
The $1,353 per night property is best for a large group, meaning more than 14 guests. The Aquaholic Sound Front 7-bedrooms Elevator Pool Theater Airbnb has 11 beds and nine bathrooms, and is perfect for guests of all ages looking for a fun place to stay in a great location. The beach is less than a .25-mile away, but the home itself features a two-story balcony, swimming pool, tiki bar, hot tub, elevator, movie theater, game room, two refrigerators, two dishwashers and much more. There are private rooms for individuals and couples, as well as bunk beds for kids, and almost everyone can see the water from their respective bedrooms. The total for the weekend, from Friday, Sept. 4 to Monday, Sept. comes out to $5,529 (including service fees, cleaning fees and occupancy taxes and fees). Planning a huge trip with the family and kids? Book soon. According to Airbnb, many other fun-loving families just this week are eyeing the location for the same dates.
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