House holiday rentals in Dewey Beach

4.94 out of 5 average rating, 258 reviews

Home in Ocean City

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

4.91 out of 5 average rating, 602 reviews

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

4.93 out of 5 average rating, 106 reviews

Home in Harbeson

Cozy Country Beach Home

Private 3 bedroom 1 1/2 bath raised ranch home on 4 acres surrounded by woods. Dog friendly with fenced backyard. Walking trail through woods. Near Lewes, Milton, Cape Henelopen and Long Neck. Short drive to Indian River Bay, Broadkill River, Rehobeth Beach and Tanger Outlets. Three miles from bike path. Enjoy local establishments including Dogfish Head Craft Brewery, Dewey Beer Co., Brimming Horn Meadery, Beachtime Distillery, YellowFins, Brickworks Brewing, and Irish Eyes. Come enjoy!

4.87 out of 5 average rating, 135 reviews

Secluded Coastal Cottage • Just 9 Min to the Beach

In a serene natural setting, this charming house offers a peaceful retreat for up to 8 guests, including children. With 3 cozy bedrooms and breathtaking view, it’s the perfect place to relax and reconnect with nature. Surrounded by state forest, you can enjoy bonfires under the stars and a variety of outdoor activities. Conveniently located, the house offers easy access to a scenic bike trail and is just a 9-minute drive from the beach, making it an ideal getaway for adventure and tranquility.

4.97 out of 5 average rating, 107 reviews

Home in Milford

Pet Friendly Home In A Private Beach Community!

Forget your worries in this spacious and serene space. Single-floor home with a very short walk to quiet Bay Beach. Spectacular 4 season Sunroom facing west over Primehook's 10,000-acre National Wildlife Refuge. Stunning sunsets and birding while dining or just relaxing after a day at the beach make this room a favorite. The home offers views of Delaware Bay. There is an outdoor shower for rinsing away the day's salt and sand. The fully fenced backyard includes a grill and space for your dog!

Superhost

4.8 out of 5 average rating, 710 reviews

Contemporary 1 Bedroom 2 level home

The unit has keyless entry system, A/C, brand new full size W/D, large patio w/grill, remote controlled open&close sky lights w/built in shades, new carpet, YoutubeTV/Netflix/Hulu/Amazon Prime Video & walk to the beach and attractions w/out crossing **pet friendly** **LOCATION** Intersection of Washington st & Jefferson St. supplied for guest: sheets blankets bath towels Shampoo/conditioner soap toilet paper paper towels trash bags Back pack type beach chairs (3) Beach umbrella Bikes (2)

4.93 out of 5 average rating, 118 reviews

Rehoboth getaway/HotTub/EV/2bd/3.7mi beach/outlets

Our 2 bed/1 bath coastal farmhouse unit is the top floor of a duplex home that is stylish and centrally located. Enjoy a lovely deck with patio lounging furniture for morning coffee. The home is close to outlet shopping, restaurants, and just 3.7 miles to the beach. Our neighborhood is just off Route 1, and tucked away - just like any gem! The space has incredible amenities with a fully stocked kitchen, free parking, fast wifi, laundry on site, and tasteful decor perfect for a beach getaway.

4.99 out of 5 average rating, 235 reviews

Home in Milton

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

For years, we searched for the perfect beach getaway: secluded, tranquil, yet close to attractions. We found it in Beachwalk. Peaceful. Private. Conveniently located at the quiet southern end of Broadkill Beach. While the north side is denser with homes and more crowded, the southern end provides a more private beach experience with far fewer visitors. The ideal beach retreat where it's just you, the sand, and the sea.

4.86 out of 5 average rating, 138 reviews

Hot Tub + Pool, Fire Pit, Cottage by Dogfish Head

This adorable beach cottage has it all, and it's bigger than it looks! With 3 full-size bedrooms, 2 full baths, and an enormous back yard with an IN-GROUND POOL, big back deck, huge HOT TUB, gas fire-pit, and dual charcoal and gas-burning BBQ, this home has everything you need for an unforgettable beach trip. You'll love the 3 KING SIZE BEDS, two of which are tempur-pedic, plus the two twin beds are great for kids.

4.99 out of 5 average rating, 202 reviews

Home in Lewes

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* from Memorial Day to Labor Day.

4.95 out of 5 average rating, 224 reviews

Home in Dewey Beach

Cozy Home at 109 Swedes St

This home built in 2013, is a cozy and bright 3 bedroom 2 1/2 bath house. It is just 1 1/2 blocks to the beach, a walk to all of Dewey's nightlife and restaurants. Also a short drive or bike ride to Rehoboth Beach. Guests will need to bring your own sheets, towels and bath matts. Provided are 5/6 beach chairs and a beach cart. June 16 to September 15, 2025 Weekly Rental Friday to Friday