Photo by Mary Pat Collins

Dagsboro Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Dagsboro

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (199)
"We had an amazing time we even extended our stay . The management I believe her name was Erin was absolutely amazing , she was friendly and helpful . The property was so clean and so convienent. We will be back great place to stay ."
The price is AU$236
includes taxes & fees
27 Nov - 28 Nov
Shore Point Cottages

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments

Coconut Malorie Resort Ocean City a Ramada by Wyndham

3.0 star property
7.4 out of 10, Good, (1236)
"A bit dated but still in good shape and decent value, big room. Water came in under the counter during heavy rain. Nevertheless, I'd stay again."
Coconut Malorie Resort Ocean City a Ramada by Wyndham

Near it all OC beaches,Assateague island.Family-friendly white horse park

10.0 out of 10, Exceptional, (26)
"My husband and I spent the weekend and the neighborhood as well as the neighbors were just lovely! John checked in to make sure we were ok and to reach out if we needed anything! We really enjoyed ourselves!"
Near it all OC beaches,Assateague island.Family-friendly white horse park

Dog-friendly 1st-floor end condo with beach entrance view - steps to the beach

8.4 out of 10, Very good, (22)
"The propery is very cozy and close to the beach entrance. Everything was very clean and organized."
Dog-friendly 1st-floor end condo with beach entrance view - steps to the beach

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

9.8 out of 10, Exceptional, (118)
"We were in Ocean City for our son's wedding. The condo fit our family and was in a great spot. We were able to walk up to the beach and take long walks on the beach. The condo was clean, large and had lots of parking. Convenient to the strip. Thank you!"
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Beautiful 4th-Floor Condo in Oceanfront Complex w/Beach Views & Shared Pool

7.6 out of 10, Good, (15)
"This condo was very comfortable for our family. The kitchen was equipped. It has 2 full bathrooms. Three beds, one sofa bed. Cable tv. Great location, beautifully decorated. The thermostat being in 72 all the time was an issue for us since the back bdrm was hot. The floor was a bit sandy when we arrived. However, it wasn't a big deal, we're at the beach! The vacasa team was helpful and polite. The condo is a gem. We loved it and we're planning to come back!"
Beautiful 4th-Floor Condo in Oceanfront Complex w/Beach Views & Shared Pool

Fabulous Oceanfront Condo on the Boardwalk w/Private Balcony & Shared Pool

9.0 out of 10, Wonderful, (52)
"Stayed in this condo for a girls weekend and it was an awesome space! The condo is big and spacious with all the comforts of home! The view off of the balcony were breathtaking! Can’t wait to go back! "
Fabulous Oceanfront Condo on the Boardwalk w/Private Balcony & Shared Pool

Beautiful suite between bay & beach w/ access to pool, private W/D, & central AC

9.4 out of 10, Exceptional, (24)
"Stayed for Country Calling festival and it was on shuttle drop off line after concert. Lots in walking distance! Condo was nicely decorated and comfortable for two people. We enjoyed the deck area very much!"
Beautiful suite between bay & beach w/ access to pool, private W/D, & central AC

Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

9.2 out of 10, Wonderful, (30)
"Our family was celebrating a milestone birthday and since we all love Ocean City, this ocean front property was perfect. The ocean and bay views are spectacular and this penthouse was very roomy for our large family. We may make this an annual event."
Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties

#1 Rated Condo, Oceanfront, with Bay View Too

10.0 out of 10, Exceptional, (290)
"I enjoyed my stay, it was quite and relaxing. Great views of the ocean and the bay."
#1 Rated Condo, Oceanfront, with Bay View Too

Newly updated condo - less than a block to the beach

9.4 out of 10, Exceptional, (27)
"Probably will rent in may"
Newly updated condo - less than a block to the beach

Ocean View Pet-Friendly Condo just steps from the Beach; Central Location

9.0 out of 10, Wonderful, (72)
"No elevator and we were on the 3rd floor. Difficult to move items up and down stairs. Otherwise it was acceptable."
Ocean View Pet-Friendly Condo just steps from the Beach; Central Location

Oceanfront Getaway w/ Free WiFi, a Private Washer/Dryer, Shared Pool, & Tennis

7.8 out of 10, Good, (43)
"The condo needs to address some maintenance issues. Left front stove burner does not work. Dried sprigs stuffed around kitchen sink faucet. We left them there for fear they were blocking water spray. A lot of spots on the carpet. Ad said there was WIFI. We couldn't get it."
Oceanfront Getaway w/ Free WiFi, a Private Washer/Dryer, Shared Pool, & Tennis

Oceanfront gem with views, pool & tennis on-site, private balcony & washer/dryer

8.4 out of 10, Very good, (24)
"Great condo overlooking the ocean. Quiet, great location far away from crowds but close enough to all the attractions. Definitely will stay again."
Oceanfront gem with views, pool & tennis on-site, private balcony & washer/dryer

Affordable dog-frienedly beach home w/private deck, gas grill, enclosed yard

8.6 out of 10, Excellent, (22)
"We loved this property! It was all one level which was great for my parents. It was also very spacious and the outside area was perfect to let the doggy have some playtime. Beds are super comfortable and it was so close to everything we needed by walking. Would stay here again!"
Affordable dog-frienedly beach home w/private deck, gas grill, enclosed yard

Capri Condo w/ Bay View Balcony, WiFi, AC, W/D & Shared Pool/Gym/Tennis/Sauna

8.8 out of 10, Excellent, (32)
"Good >views, other guest, cleaning staff, and overall experience Bad > when trouble hit it was not prompt. Tech help over the phone was not as informed as cleaning staff"
Capri Condo w/ Bay View Balcony, WiFi, AC, W/D & Shared Pool/Gym/Tennis/Sauna

Safari Apartments

3.0 star property
9.2 out of 10, Wonderful, (29)
"Property was newly renovated, and everything was new and clean. Had issue with lock but staff was very fast and efficient on assisting us. Enjoyed stay and would definitely come again."
Safari Apartments

Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!

9.6 out of 10, Exceptional, (71)
"Donnie was a great host & this is a great property in the Dewey Beach area! He was very communicative prior to check in and with the check out process. It was the perfect place for us during our stay. We hope to stay here again!"
Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!

Amazing View from 2 BR 2 BA Beachfront Building with Indoor Pool

9.4 out of 10, Exceptional, (45)
"Just love this beautiful, well maintained condo! Great ocean and bay views! "
Amazing View from 2 BR 2 BA Beachfront Building with Indoor Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Dagsboro
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Dagsboro you may be interested in

Grand Hotel Ocean City Oceanfront

3.0 star property
9.0 out of 10, Wonderful, (2435)
"Very nice property "
The price is AU$148
includes taxes & fees
1 Dec - 2 Dec
Grand Hotel Ocean City Oceanfront

Fenwick Inn

2.0 star property
8.6 out of 10, Excellent, (1797)
"Really nice and clean "
The price is AU$150
includes taxes & fees
3 Dec - 4 Dec
Fenwick Inn

Holiday Inn & Suites Ocean City, an IHG Hotel

3.0 star property
9.6 out of 10, Exceptional, (1073)
"The property is on the boardwalk where its less busy lots of fun, great dining within a mile everywhere in OCMD during summer. During winter this place rocks. 4 great hotel restaurants within mile. Restaurant here is tasty. Heated pool 5ft deep about 30ft x 15ft like octagon. They regularly drain clean refill and warm up. Today the pool is fresh. All staff friendly and accomodating. Oceanfront 1bdrm w four people very comfortable big jucuzzi jet tub with rainfall shower. We decided to stay...
The price is AU$159
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn & Suites Ocean City, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Dagsboro?

Yes, there are holiday rentals close to the most popular sights in Dagsboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dagsboro has to offer?

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15: This holiday home rental outside of Dagsboro is located on the waterfront, and has an outdoor pool, a patio and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Dagsboro?

Expedia has 6 holiday rentals for your stay in Dagsboro.

What can I see and do in Dagsboro?

While exploring the area, visit family-friendly sights like Carousel Ice Skating Rink, or get outside and enjoy nature at Holts Landing State Park. In the wider area, you’ll find Baywood Greens Golf Course and Baywood Greens.

What are holiday rentals like in Dagsboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dagsboro. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.