Vacation rentals in Dagsboro

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Top-rated vacation rentals in Dagsboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Condo in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview Retreat

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

Mar. 1 – 8

$208 CAD per night

Guest favourite

Guest suite in Rehoboth Beach

4.98 out of 5 average rating, 122 reviews

Treetops beach getaway walkable to beach/boardwalk

East of Route 1, equidistant to both Rehoboth & Dewey beaches, about 1/2 mile easy bike/walk. Brand new for 2021, this fully equipped guest suite offers a private entrance, bedroom with a king bed on an adjustable frame, full bath, laundry, and a kitchenette. There is NO STOVE in this unit but we have provided a microwave and toaster convection oven/air fryer for easy beach meal prep. There is also a gas grill for barbecuing. Please note that this unit is strictly limited to 2 mature adults.

Mar. 27 – Apr. 3

$175 CAD per night

Guest favourite

Apartment in Greenwood

4.97 out of 5 average rating, 479 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)

Nov. 24 – Dec. 1

$112 CAD per night

Guest favourite

Tiny homes in Ocean View

4.97 out of 5 average rating, 116 reviews

The Bohemian Rhapsody

*Carefully & thoroughly read entire descriptions & click on photos & read captions!* Enjoy a rustic "glamping" experience in 2 Bohemian themed sheds-the Grateful Shed & Surf Shack...less than 5 miles from beautiful Bethany Beach, DE! Private driveway & entrance, outdoor bath house w/space available to set up tents. We can host up to 6 humans (upon approval) & 2 canine kids. Electric,Wifi,fire pit,beachyard,outdoor grill. Close to area beaches, boardwalks, restaurants & more! No extra fees!

Sep. 15 – 22

$163 CAD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 530 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.

Dec. 20 – 27

$188 CAD per night

Guest favourite

Place to stay in Frankford

4.92 out of 5 average rating, 141 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!

Jun. 4 – 11

$211 CAD per night

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 149 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!

Oct. 11 – 18

$181 CAD per night

Guest favourite

Apartment in Frankford

4.98 out of 5 average rating, 123 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. 15 – 22

$213 CAD per night

Guest favourite

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.

Sep. 13 – 20

$172 CAD per night

Guest favourite

Home in Milton

4.79 out of 5 average rating, 197 reviews

Country living near beach/Dogfish Head/Dewey Beer

Vacation at the beaches but stay in the country! TWO large bedrooms and full bath with everything you need. 10 minutes from Lewes beach, Cape Henlopen State Park and the Tanger Outlets. 20 minutes to Rehoboth Beach and only about 5 minutes to Dogfish Brewery in Milton. 1 mile from the new Dewey Beer Brewery, the Lewes/Georgetown bike trail. Bring your bike and ride into Lewes! 5 minutes to Sports at the Beach!

May 12 – 19

$167 CAD per night

Guest favourite

Condo in Ocean City

4.99 out of 5 average rating, 175 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

Feb. 3 – 10

$212 CAD per night

Guest favourite

Home in Ocean View

4.87 out of 5 average rating, 446 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. 14 – 21

$172 CAD per night