Vacation rentals in Dagsboro

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Top-rated vacation rentals in Dagsboro

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Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 106 reviews

Quiet Water View Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Nov 9 – 16

G$28,949 GYD per night

Guest favorite

Apartment in Dewey Beach

4.95 out of 5 average rating, 133 reviews

DeweyBeach 1 BR + sleeper sofa. Walk to the beach!

Enjoy all of Dewey Beach at this delightful 1 BR, ground floor, apartment on the north side of town. 1.5 blocks to the beach, and 3 blocks to the start of restaurants and music venues. Quiet, relaxing location on a side street. Perfect for a small family or group of 4 friends! Custom self check-in keypad code for Private Entry sent upon booking. Professionally cleaned + bed made before your stay. 4 beach chairs, 1 on-property parking spot + 1 free Street Parking Passes provided at no charge!

Dec 23 – 30

G$18,575 GYD per night

Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 477 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Sep 19 – 26

G$17,163 GYD per night

Guest favorite

Tiny home in Selbyville

4.98 out of 5 average rating, 210 reviews

Destination Location! Farm Animals, Tours, Beaches

Scratch staying in a tiny house off your bucket list! Escape the Ocean City crowds and slow life down at this Garden Hideaway. Situated on a ranch just minutes from the beach, this unique home has a barnyard of fuzzy animals ready to greet you each day. Curated to both inspire joy and create presence, enjoy a simple morning and sip coffee with Fonzie the alpaca, Charlotte the mini-pig and a front yard of silly goats sure to entertain. This is a magical stay that we're certain you'll love!

Sep 18 – 25

G$27,919 GYD per night

Guest favorite

Home in Ocean View

4.92 out of 5 average rating, 531 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our 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 TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Apr 28 – May 5

G$25,429 GYD per night

Guest favorite

Place to stay in Frankford

4.92 out of 5 average rating, 140 reviews

Seaside Sunroom, No cleaning fee, No Wi-Fi.

Bright space, attached to main house, but has it's own entrance, full bed with memory foam, bathroom with tub, coffee maker, mini fridge; live plants in room, 10 min car ride to Bethany Beach. Access to backyard seating, chimnea and outdoor shower (May 1 to Nov 1). No WIFI, no TV. Beach gear available.There is no access to or from main house, but some muffled noise can still be heard during the day, including a small dog. Self check in with a key, but no late check in, please, ty!

May 10 – 17

G$21,897 GYD per night

Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 222 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Nov 8 – 15

G$23,052 GYD per night

Guest favorite

Guest suite in Berlin

4.99 out of 5 average rating, 148 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

Jan 30 – Feb 6

G$23,810 GYD per night

Guest favorite

Apartment in Frankford

4.98 out of 5 average rating, 122 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Oct 8 – 15

G$25,935 GYD per night

Guest favorite

Apartment in Milton

4.96 out of 5 average rating, 132 reviews

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front.

May 2 – 9

G$24,883 GYD per night

Guest favorite

Home in Georgetown

4.85 out of 5 average rating, 106 reviews

Maplewood - Simply Comfortable, Dog Friendly

Have fun with the whole family at this stylish place in the center of it all. Near the beach, away from the crowds. Local attractions: Sandhill Fields - .5 miles Sports at the Beach - 1 mile Dogfish Head Brewery - 5 miles Lewes Beach -8 Cape May Lewes Ferry Terminal Cape Henlopen State Park Tanger Outlets - 12.4 miles - 13.9 miles And lots of other tax free shopping. Rehoboth Beach Boardwalk - 17.5 miles Dover Downs - 39.1 miles Many other attractions nearby.

Aug 27 – Sep 3

G$30,989 GYD per night

Guest favorite

Home in Ocean View

4.87 out of 5 average rating, 445 reviews

Private place near Bethany Beach

Our place is close to Bethany Beach and conveniently located to Fenwick Island, Ocean City Maryland, Rehoboth Beach, Tax Free Outlet Shopping, Golf, Fishing, Surfing, or Hunting. You’ll love our place because of the quiet wooded location perfect for relaxing near all the beaches of the Delaware Eastern shore. This area is a wonderful place to visit all year round.

Dec 15 – 22

G$23,814 GYD per night