Renting an Airbnb at Dewey Beach, Delaware

Every summer for over a decade, my mom, sister, and I have gone to Rehoboth Beach, Delaware for a long weekend. When my daughter came on the scene, she joined us. We always stay at the same hotel, we go to the same restaurant Saturday after being at the beach for crabs (though my mom gets lobster), we always look forward to this tradition. But this summer, the idea of staying at a hotel and dining at restaurants and visiting a busy beach did not sound appealing. My family and I had the month of July open, thinking this summer we’d do another road trip. Last summer we did one up part of the East Coast, stopping in Philadelphia, New York, and Boston and ending with a week in a cabin in the Northeast Kingdom of Vermont. Early on in 2020 we saw that there would not be any road trips in our future.

We accepted the fact that there wouldn’t be any vacations. No 4th of July festivities, no Labor Day festival, no community pool to visit. We knew it was necessary to stop the spread and to stay safe. But our four walls started getting to us and I began researching a safe and reasonably priced vacation and visiting the beach seemed like the best idea. We live just a couple hours from the Delaware beaches – no need for a rest stop or to refuel the car. The beach is open and outdoors which is the safest place to be right now. And if we got a rental house we could make our own foods and have our own bathrooms and be able to sanitize and all that stuff.

Why We Chose Dewey Beach, Delaware for Our Family Vacation

I started looking for a rental house in Rehoboth Beach at the end of June and realized that everyone else had the same exact idea. Houses were booked through Labor Day, or else prices were jacked up so high they were expecting $800 a night for a dilapidated shack six miles from the beach. I expanded my search from Rehoboth Beach to other beaches in Delaware that were a reasonable drive away.  I chose Delaware over Maryland (where I live) because I had seen videos and photos of the crowds at Ocean City and I didn't want any part of it. Back when I was a bachelorette and newlywed, Dewey Beach was my summer home away from home.  While it's known during the summer months as a party town, I had visited Dewey in the off-season and found the atmosphere to be drastically different.  After Labor Day, it is quiet and slow-paced and the beach is dog-friendly.  While Dewey isn't known as a foodie town like Rehoboth, we didn't plan on dining in restaurants and instead cooking ourselves or choosing takeout, which could easily be picked up from Rehoboth right down Coastal Highway and still be hot by time we got back to our Airbnb.

This is such an unusual year, I decided not to be tied down to the school schedule and expanded our possible vacation dates beyond Labor Day. Whether or not our county decided to have 100% distance learning or a hybrid, I felt it was in my kid’s best interest to get her out of the house and having a getaway. And when I opened up our calendar it opened up more houses and lower weekday rates and many of them were in Dewey Beach, Delaware.

Finding the Right Airbnb in Dewey Beach, Delaware

While it was just me, my husband, and our tween, we had specific desires for a comfortable Airbnb experience for our beach getaway. What we desired in a beach house:

  • At least two bedrooms
  • At least one and a half bathrooms, preferably two full bathrooms
  • Central air conditioning
  • Wifi
  • An area that can be a workspace and be closed off for our kid's distance learning
  • A roomy living area where we could enjoy a movie together but also have space for yoga or other exercises.
  • A short walk to the beach (four blocks or less so we could easily carry chairs, boogie boards, and such)
  • A complete kitchen to cook proper meals
  • Dog friendly

The Dewey Beach house we rented from Airbnb. The “Crow's Nest” was closed but the rest of the house was open to enjoy. Four bedrooms, 2 1/2 bathrooms, plenty of indoor space, and just two blocks from the beach.

We realized most homes were booked weekends but not weekdays, and the weekdays were a far lower price on many Airbnbs in Dewey Beach. We chose this house from Airbnb from Monday, Labor Day, until Friday, September 11th. The house was bigger than we needed but the price right on budget and a great location. We booked it so early we thought possibly we could bring another family or members of our extended family if things improved in our country, but by the time we were planning our trip, we knew it was safest to go alone. While the house says it is not pet friendly, I contacted the owner through Airbnb and shared photos of our dog, his weight, and temperament and they said our dog would be fine for an additional pet fee and if we would keep the dog crated when we weren’t in the house with him.

Preparing for a Road Trip during COVID

We did not want to have to stop on our trip for gas, food, or the facilities.  Our goal was to be in contact with as few people and surfaces as possible. We filled our gas tank in our neighborhood using precautions, packed snacks, and chose to leave after rush hour to make our drive as short as possible. We used the facilities before we left, but I also packed a PStyle in case nature called so I could take care of things on the side of the road instead of at a gas station.  

Traveling on Labor Day was genius; we were going against traffic the entire way and the trip was just a hair over two hours in length.  I would highly recommend doing this if your schedule permits, the bumper-to-bumper traffic from the Bay Bridge all the way onto 404 was a painful reminder of summer beach vacations past. Even once we reached Coastal Highway, traffic was quite light. 

We brought our own pillows, bedding, towels, and even brought our own dishtowels and cloth napkins. We also packed cleaning supplies and sanitizing wipes so we could do our own wipe-down upon arrival.  In the car, we had latex gloves, disposable masks, and a bottle of hand sanitizer.  We brought enough cloth masks to have two per day per person and each of us had our own bottle of hand sanitizer to carry with us when out and about. 

Our Family Getaway to Dewey Beach, Delaware

Dewey Beach is so easy to get to from the DC area, and the town itself is very small so it's hard to get lost.  We arrived at our house and with the code our Airbnb host supplied us, we got the key from the lockbox, and let ourselves in.  My sister had scored a few tubs of Clorox Wipes earlier in the summer when by chance she was at Target when they refilled the shelves and we had kept one just for this trip.  We used them to wipe down most surfaces from front door to bathrooms to bedside lamps, then washed up and went out to get our luggage.  

So happy to visit the beach after six months at home!

Our dog, Oscar, enjoying his first visit to the beach! y husband's shirt is from Old Navy (old; similar), hat is from Goorin Bros., shoes are Brooks (old; this page explains them)

Once unpacked we headed to the beach. It was our dog’s first time at the beach so we timed our visit at 5:30 when the beach opens to dogs (FYI the beach is open to dogs at all times of day after September 15, more details below). It was so fun to see all the dogs running around and playing with one another. Our dog is a rescue and we’ve only had him a year so we kept him on a leash the whole time but let him sniff and romp around with the other pups while also getting our feet in the surf and enjoying being outside while being socially distant from others. Everyone was respecting one another’s space on the beach, staying two taut leash distances from one another and spreading apart when passing on a surfside walk. Once the sun started to set, we headed back to the house to make dinner and prepare for distance learning school the next day.

child sitting at a desk in front of a computer with a window overlooking the Atlantic Ocean

Kiddo set up for distance learning at our beach house

The next morning my husband made banana pancakes while our kid got ready for school. The house had a sunroom with doors to separate it from the rest of the house, and in the room was a desk and chair with outlets and shelves right next to it – perfect to be set up all week for distance learning. We had no connectivity issues and her day of online school was a success with a much nicer view than at home! 

Walking along Coastal Highway heading back to my house after encountering several without masks and not social distancing. Sunglasses from Ray-Ban, mask from Candace Cort, t-shirt from a Beth Ditto concert.

My husband made oatmeal cookies – we brought oatmeal but found all the other ingredients and baking supplies in our Airbnb

Once our kid was up and running with school, I decided to go for a walk on the beach.  Heading to the beach, I was surprised to still see the sidewalks full of people considering Labor Day was over.  On the beach before noon was quite full and the only way to have a comfortable amount of space to set up camp one would have to be far back near the dunes.  On the surf was worse, people were not moving to let people through and it was hard to take a walk without getting uncomfortably close to strangers.  I headed back to the town thinking I could walk through neighborhoods but found many people out and about without masks, not making space to pass on sidewalks.  Concerned and annoyed, I headed back to our beach house and took care of buying groceries (see below). 

Packed up for a day at the beach! The Tommy Bahama backpack chair was borrowed from our Airbnb; the house we rented is the one in the background with the “crow's nest” on top. My shirt is from St. James, shorts from SLiNK Jeans, sandals from Birkenstock.

Having plenty of space on the beach on a beautiful day in Dewey, my husband holds onto our surf-fearful dog. Tote bag is SCOUT by Bungalow, towel on the boogie board is actually a poncho from Pendleton.

When school was finished for the day (and no homework!) we all got changed and headed to the beach hoping things would be more chill in the late afternoon. We were thrilled to find the beach far less crowded and individuals being considerate of one another’s space on sidewalks there and along the shore. The weather was fantastic, and we enjoyed a couple of hours boogie boarding and body surfing. While our dog loved the beach the previous day, this day he was more fearful so one of us stayed at the chairs with him in our lap during our beach visit.

Enjoying the big comfy couch in the Airbnb's living room, watching TV after dinner.

We came home and cooked burgers for dinner and then enjoyed an episode of America’s Got Talent on TV as a family.  Just being in a different environment made everyday things feel special. 

This swimsuit did me well on this vacation. The swim top has underwire, molded cups, is bra-sized, and can be made racerback. While I picked blue it comes in many colors and prints. It has a variety of bottoms to coordinate with it; I chose this bottom.

Leaving the beach before the torrential rains. Monogrammed towel from Lands' End, my jacket is from Talbots (old; this is similar).

The next morning was gray and gloomy. I went for an early morning walk before the family woke and got caught in the rain so I came home and connected with a friend and we decided to do a Peloton yoga class together in our respective places, and then have a FaceTime coffee date before she headed to work. The rain was too hard to do anything outside so while our kid did school, I did some work and my husband did some Peloton app workouts (we brought our hand weights), baked cookies, and took a nap. When school ended (Wednesdays are a shortened school day), the rain had stopped so our kid and I did a quick change, grabbed just towels, and headed to the beach to enjoy it as long as we could. We got a little over an hour of fun in the surf before it started to sprinkle. We grabbed our stuff and headed home and halfway there the skies opened. We laughed as we hid under towels for the remainder of our walk, took hot showers, and changed into sweats. Our kid did her bit of homework and we had taco night.

Activewear as streetwear and beachwear! Top from Athleta, as are the shorts which have pockets for my mask and phone. The shirt around my waist is very old, this is similar. I used it to tie my sneakers to it when I was on the beach.

Thursday morning was also gray, but the rain had let up. My husband headed out for a beach run, and when he came back I then went out to enjoy the outdoors. It was a gray and slightly humid day, but it was still wonderful to spend time at the beach. I went for a long walk, did some yoga and stretching on the sand, and did one of my favorite beach pastimes – walking through neighborhoods checking out beach houses and dreaming of which house I’d own if I won the lottery I never play.

Getting our daily family beach time in. My striped shirt is from J. Crew, I'm wearing Soma joggers pulled up to my knees. My daughter's AC/DC shirt is from Aeropostale.

After school, our kid had a bit of homework so we had her do it before we headed back to the beach. Since it was still gray and a little cool, we didn’t put on bathing suits and just went to hang out and take a walk. It was still lovely.

Saying goodbye to the Atlantic Ocean our last day in Dewey Beach

Friday, we all went for an early morning walk on the beach before breakfast and school. Our kid did her first class while my husband and I packed up the car, took out the trash, and tidied up the house. She finished her first class right around checkout time and we got home in time for her to attend her last two classes of the day.  While we didn't have perfect weather, we still had an amazing beach getaway!

Contactless Grocery Shopping in Dewey Beach

We brought some groceries with us but needed additional provisions (and sunscreen that we forgot). There are many ways to get contactless groceries and other necessities while at the beach. Several of the stores are part of Instacart and can deliver groceries right to your beach house. Using Instacart at home, I know it can take a long time and get complicated with out of stock items.  As a family with dietary restrictions, it can be a laborious process.  We chose to order groceries online and do a contactless pickup. 

Our dog excited and permitted on the beach in Dewey Beach, Delaware

Getting a Dog Permit in Dewey Beach

Dewey Beach, Delaware is one of the few beach towns on the eastern seaboard that is dog friendly.  I didn't even realize that a dog permit was needed in Dewey Beach to let your pet on the beach.  Thank you to the reader who let me know!  She also let me know that the permits are bought at the Dewey Beach Town Hall on Rodney Avenue.  She also provided the intel that you don't need to go into the Town Hall to get the permits.  There is a kiosk in the parking lot; the kiosk looks to be just to pay for parking but from it you can also purchase 3-day ($5) and 8-day ($10) dog permits.  The kiosk is open 24 hours a day and can take credit cards as well as cash (must have exact change). Dogs are allowed on the beach from 5:30 pm until 9:30 am May 15 until September 15; the rest of the year dogs are allowed on the beach at all hours.

The water was warm and the surf was less populated making it easier to social distance

Our Experience at Dewey Beach during COVID

While the first day in Dewey was alarming with the lack of masks and social distancing, I found the rest of our time in Dewey Beach to be very quiet and those I encountered to be respectful of others’ personal space. Many when they think of Dewey Beach, Delaware, they think of drunk college kids and young adults. And sure, the summers in Dewey are very much like that but off-season, it’s very quiet. The majority of people we saw were couples over 40 and three-generation families with kids young enough to not yet be in school. The neighborhood of our rental house seemed 50% rentals and 50% year-long residents who were quiet individuals and couples. Most of the bars and restaurants in Dewey Beach were open, and several had modified their parking lots and outdoor areas to accommodate outside dining. In general, we found houses in Dewey to be a better value – same price as Rehoboth and other beaches while offering a closer location, more space, or a more recently updated rental.

Our Airbnb beach house was good. It was clean, well-appointed, great location, and the host was phenomenal with communication. While I knew from the photos and previous renter reviews that the house didn’t have a deck or porch, I didn’t realize how very much I would miss it. Rainy days would have been more enjoyable out on a porch, late nights while the kid was asleep would have been lovely on a deck or patio. The house had a picnic table in the small patch of grass in front, but it was right on the street and the grass and table were soaked from the rain. The kitchen was great, plenty of cooking and baking tools, and the pantry had basics in it so we were able to use them along with our groceries to put together pancakes, oatmeal cookies, and peanut butter cookies and have evening tea even though we forgot our tea bags. The sunroom was our favorite space, with a spectacular view of the sunset over the Rehoboth Bay right from one of the couches. The back door was into the laundry room with a tile floor and next to the outdoor hose so it was easy to keep sand from spreading all over the home. The house can comfortably sleep 10 with a toddler mattress under one of the beds and large comfy couches just in case. The garage had boogie boards, sand toys, beach chairs, and more. While the house says bring your own linens, they did have some extra blankets and beach towels and such in case you’re in a pickle.

Loved the short easy walk to the beach everyday!

Why We Chose Airbnb for our COVID Getaway

This doesn’t sound like an incredibly thrilling vacation, but for the kind of year we’re having, it was amazing. Being out of the house and having a different environment was the reset we all needed. Because our school system has 100% distance learning, she can go to school anywhere that has WiFi. You can have a fantastic vacation without having to interact with strangers or be in uncomfortable social or indoor situations. Rental homes mean you don’t have to interact with hotel staff or other patrons and have a kitchen to easily cook all your meals (or a place to enjoy delivery or contactless takeout).  We specifically chose Airbnb because I appreciated the details about houses and the ability to communicate with hosts.  I was able to find out when the house was cleaned and how, choose a contactless entry to the home, and read detailed reviews from previous renters sharing their experience with the house, sanitation, and communication with the host.

This is a year of new normals. New ways to work, to socialize, to dress, and also to travel. This experience made me feel hopeful, knowing there is a way to enjoy getaways without putting myself, my family, and strangers at risk. I know this isn’t for everyone, and I know some are more comfortable with aspects of travel in 2020 that I am not. But this experience left me feeling renewed, feeling less hopeless, and desiring of another short road trip to a rental home in the future.

25 Comments

  1. Judy
    September 18, 2020 / 11:43 am

    Love your vacation post. With your great writing, I could feel the sand and water rushing between my toes. Family so adorable. Not to mention the little guy, what a lucky rescue. Have a great Fall.

  2. Linda
    September 18, 2020 / 8:50 am

    I see that your daughter is reading Wonder. Does she like it?

    • September 18, 2020 / 8:58 am

      She loves it! We saw the movie a while ago and I got her the book after but she didn’t read it then. This summer she’s been going through her bookcase and reading what she hadn’t yet covered and is really enjoying it!

  3. SusieG
    September 17, 2020 / 2:47 pm

    Such perfect timing you have, Alison! We were just considering a break to the beach (OC, Rehoboth, or Dewey) for my daughter’s October birthday. And we also plan to bring our rescue dog. Really appreciate all the tips, as we are also still trying to be very careful re COVID.

    Fun side note? Moved out of the District and am now a fellow Marylander 🙂

  4. Linda B
    September 17, 2020 / 10:20 am

    I loved reading about your trip–got vicarious pleasure out of your descriptions! So glad your family was able to have this experience!

  5. Diane
    September 17, 2020 / 9:07 am

    We did something similar this year, renting an Airbnb in upstate New York. It was so relaxing to have a change of scenery, I almost didn’t sleeping in a strange bed!

    • September 18, 2020 / 7:01 am

      Right? My back was happy to come home to my bed but the rest of me didn’t want to leave!

  6. Tee
    September 17, 2020 / 8:52 am

    Thank you for sharing your experience and vacation.
    I missed the entire summer due to my health issues and fear of getting sick. My sister-n-law and I try to enjoy the beach EVERY year, this year being no different. We had to cancel our beach/board walk front apartment in Rehoboth due to the crowds we saw on the beach everyday.
    After reading your experience in Dewey, maybe we have more options to explore for 2021( if it’s safe next summer)
    Thank you again, and cute family (daughter and Oscar).

    • September 18, 2020 / 7:00 am

      I’m sorry you had to cancel your vacation and hope you can return to the beach safely in 2021!

  7. RoseAG
    September 16, 2020 / 10:44 pm

    I’m thinking that if your house was in Dewey you were watching the sunset over over Rehoboth Bay.

    • September 18, 2020 / 6:58 am

      You are so right, ack! Thank you, it was updated.

  8. Elizabeth Kay
    September 16, 2020 / 10:02 pm

    Thank you Alison, this is very helpful! My son is getting married in early October— he and his fiancé have chosen an “Elopement package” at an historic B&B in Savannah, GA, just a few hours from our hometown. They provide everything for the wedding, including an officiant, flowers, cake and an intimate reception. The bride and groom are allowed 4 guests (!) so the parents of the wedding couple are the lucky 4 guests! Your info here has made me more confident that a short, safe trip is doable!

    • September 18, 2020 / 6:59 am

      That sounds like a beautiful, intimate event. I hope you have a lovely time and congratulations!

  9. Jax
    September 16, 2020 / 9:47 pm

    Hi Alyson, so glad you were able to get time away. We just had our own family vacation 2 weeks ago (during a week that ended up being pretty decent and just before the horrible orange skies in the Bay Area) in the Russian River area of Sonoma (and also just ~30 mins from the coast, so we got both river and ocean beach time). We had planned to have our vacation beginning of August, but the airbnb host canceled on us less than 2 weeks before. We were not able to find something comparable on short notice, so we postponed it and were able to find another place. However, that meant my kid had to attend online school like yours did. That was my one regret that she still had to be online. Still, it made a huge difference to us all to get a change of scenery. I just loved getting away from all the unfinished home projects at home…
    BTW, did you see this recent NYTimes article about flexcations? I guess that’s what we had!
    https://www.nytimes.com/2020/09/08/travel/fall-resorts-coronavirus.html

    • September 18, 2020 / 6:59 am

      I am so glad you were able to get away. And thank you for this article, I didn’t see it!

  10. Book Goddess
    September 16, 2020 / 8:17 pm

    Alison, did you put in that link about “Florida Mom Brutally Murdered” or were you hacked or something? It doesn’t seem like something you would include at all.

    • September 16, 2020 / 8:26 pm

      That’s from my ad network and something I DEFINITELY do not want on my site. Thank you for notifying me, I’ll flag it.

      • Judi DiPillo
        September 18, 2020 / 1:10 am

        If you’re a writer, you should make sure you spell ” definitely ” correctly. People do notice.

        • September 18, 2020 / 6:57 am

          It took me a minute to figure out where you saw that and I saw I misspelled it in a comment, not the actual post. A comment that I read while in transit, replying on my phone, freaked out about something inappropriate showing up on my website. I may consider myself a writer but I do not consider myself perfect. I am also not a copyeditor and I am a staff of one. Thank you for copyediting my comment section, I appreciate the support and edited it accordingly.

  11. Lee
    September 16, 2020 / 7:57 pm

    Love that y’all got away for a vacation & had a good time. You really live in such a fabulous part of the country, with your access to great cities, beach areas, etc. My family of 3 had a similar trip this summer where we were easily able to social distance & keep to ourselves—just being away was wonderful. Thanks for sharing your trip.

    • September 18, 2020 / 8:58 am

      I’m so glad you were able to get away!

  12. yasmara
    September 16, 2020 / 4:44 pm

    We are headed to a beach house rental in early October – still warm enough for transplanted Northerners to visit NC beaches. One kid will need to do 1 day of online school while we are there, the other is on Fall Break. I can’t wait! We are using many of the same strategies as you – leaving on a weekday after work, staying in a house by ourselves, bringing most food or getting take-out.

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