If your ideal beach vacation is when the crowds (no restaurant reservations!) are gone, you’re in luck. Come fall and winter, rental availabilities are not only unlimited but prices are at their best.
“The summer season is over the after the third week in August when all the kids go back to school,” says Charissa Joachimowski, rental manager for Wilgus Associates in Bethany Beach. “Rental prices start to go down immediately and they crescendo a bit downward each week after that.”
Additionally, shorter weekend rentals are more common in the fall, as opposed to the standard seven-day commitment that comes with summer beach rentals, adds Steven Gilbert, president of Bethany Beach Home Rentals. And this season, there might be a greater choice of properties.

“In talking with others in the business, Delaware summer beach rentals are down by about 12% this year over 2022,” Gilbert says. “Some think it’s the economy, but I believe those people who were hesitant last year to go on cruises or take long-distance airplane flights are doing so this season rather than coming to the beaches.”
This holds true of all types of rentals—houses, condominiums, apartments, and even hotel and motel rooms, whether for individuals or for larger groups of family and friends.
Here, rental agents and property owners share their tips for making the most of rentals from now through winter.
Use your bargaining power
“As rental agents, we don’t ask for people to lower prices, but on a case-by-case basis, some property owners do offer special fall discounts,” says Adriane Gallagher, rental manager for Berkshire Hathaway in the Lewes area.
Don’t hesitate to make a counteroffer for a property you think is overpriced for the season, or perhaps to bargain for an early check-in or for a later checkout time. Also, if you have a fixed rental price in your budget, the rental agent will try to find the best offer.
Upgrade your location
Joachimowski says some of the best places that are always booked solid in the summer might be available. “We have more properties in the fall that are on the east side of Highway 1,” she says. Translation: Your chances of getting something elegant near or on the sand are much greater. And who doesn’t want a rental overlooking the ocean?
“The best values in the fall are the amenity-rich, resort-style communities,” Gilbert says, “such as the Coastal Club, Bear Trap Dunes and Bayside Resort. The rates are such that if you have four or more people, you can rent a house with all the options for the same price you can rent hotel rooms for the same number of people.”
You also are more likely to get additional rental space for the same or even lower prices come autumn.
Decide on how much activity you crave
While people who love the beach in the fall like to avoid the crowds, most still want a choice of places to shop and eat. “Lots of people want to still be in a town area where they can walk around,” says Gallagher, and some of the private shuttles and public transport close down in the fall or have reduced schedules.
If you want to walk or limit your driving, check in advance to see whether the restaurants located in the area where you plan to rent are open only on weekends or not at all. That could force you to reconsider where you want to vacation.
“Lewes is a great area to rent in the fall and winter because people live there [year-round] and nothing closes down,” Gilbert says. “By contrast, Ocean City in Maryland becomes a ghost town after the first few weeks.”
Those who want to commune with nature might also consider B&Bs located in more remote areas. Additionally, unlike other rental properties, they might allow you to bring your pets. Both are calling cards for Lazy L at Willow Creek, a five-room and one cottage B&B on the outskirts of Lewes. “We are right on the marsh with beautiful views, a fireplace [and] a heated pool, and we are very dog-friendly,” says innkeeper Meta Lyons-Law.
Check the amenities
In addition to fireplaces and heated pools, the resort-style communities have group amenities to offer, Gilbert points out. “For people who love to play golf, these communities are great,” he says. “Bear Trap Dunes, for example, has three gold courses as well as clay tennis courts.”
Private homes with fireplaces and outdoor hot tubs are always in demand for those who like their beach time with a bit of chill in the air.

Of course, once the shoulder season is over, people are still looking for rentals in the winter when the prices are lowest and the solitude is greatest. Even though few shops remain open and many restaurants are closed or have reduced hours, the opportunity to take long walks along the beach to the sounds of the pounding Atlantic surf will always be there.
Related: 5 Things to Do at the Delaware Beaches Before Summer Ends