Dewey Beach Holiday Rentals

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Holiday Rentals in Dewey Beach

Serenity Amid it All. Dog friendly PET FEE, WiFi, outdoor shower, grill
9.8 out of 10, Exceptional, (254)
"The property was exactly as described, perfect location and cozy atmosphere. Great for some old friends to catch up. Porch and outdoor shower were super cool. Great place"
Serenity Amid it All. Dog friendly PET FEE, WiFi, outdoor shower, grill
Town of Dewey Beach condo with balcony ocean view, central A/C, & W/D - dogs OK
8.4 out of 10, Very good, (23)
"Clean. Well maintained. Host was pleasant when I reached out. Location was perfect for the Dewey Goes Pink event. Will definitely stay here again!"
Town of Dewey Beach condo with balcony ocean view, central A/C, & W/D - dogs OK
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!
Fantastic Location on Saulsbury St with a 3-night weekend option
9.8 out of 10, Exceptional, (60)
"You cannot beat the location of this place! Unreal! Walking distance to everything! The space was amazing! The cutest outdoor area! The owner was very quick to respond to any questions! Very impressed and happy with it all and can’t wait to go back! And Dewey is just so amazing in itself 🩵⚓️🦀🌊🐚"
Fantastic Location on Saulsbury St with a 3-night weekend option
Direct Ocean Views from your bed & screened-in deck.Pet friendly! 2br 2bth
10.0 out of 10, Exceptional, (56)
"My cousin and I had such a great time in Rehobetg"
The price is AU$1,164
includes taxes & fees
11 Dec - 12 Dec
Direct Ocean Views from your bed & screened-in deck.Pet friendly! 2br 2bth
Luxury Bayfront Penthouse Condo 1 block from the beach. Overlooking rooftop pool
10.0 out of 10, Exceptional, (64)
"My mom and I decided we needed a long weekend together on the Eastern Shore. We found the perfect spot in Dewey Beach. The weather in October was wonderful. Restaurants still open and no waiting for a table. We enjoyed staying in this condo. 2 bedrooms 2 bathrooms just like the pictures showed. Very nicely decorated with a view of the bay and pool. Amazing sunsets in the evening. It was quiet and relaxing. Just Perfect. "
Luxury Bayfront Penthouse Condo 1 block from the beach. Overlooking rooftop pool
Dewey Beach home with enclosed lanai, hot tub, patio & firepit - 1 dog welcome
9.4 out of 10, Exceptional, (20)
"We love the house and think it's great. There are a lot of pleasant surprises (papertowels, dish soap, bathroom soap, trashbags, beach chairs, bikes, cleanliness, hairdryer, kitchen amenities). We would stay here again."
Dewey Beach home with enclosed lanai, hot tub, patio & firepit - 1 dog welcome
Beachfront Baby💛 Beautiful & New!🌟The only way to stay @ the beach❣️Spacious
10.0 out of 10, Exceptional, (64)
"This property was amazing. I love going to the beach during the off season. This had been a rough year with loosing family and animals. It was a last minute trip and we needed to find a place that we could take a dog. The property was amazing. Maureen was a great communicator"
Beachfront Baby💛 Beautiful & New!🌟The only way to stay @ the beach❣️Spacious
Best of Dewey! 2 BR1.5 bath steps to the Ocean on popular McKinley!
9.8 out of 10, Exceptional, (50)
"Mike was great! Super quick to communicate, was accommodating and the place was perfect for us! Great location!"
Best of Dewey! 2 BR1.5 bath steps to the Ocean on popular McKinley!
Enchanting condo w/ ocean-view, with balcony, pool, washer/dryer, & dog-friendly
7.8 out of 10, Good, (25)
"Great size condo with plenty of outdoor decks and patios"
Enchanting condo w/ ocean-view, with balcony, pool, washer/dryer, & dog-friendly
DeweyBeach 2BR Ground Floor Condo. Family-Friendly, quiet, clean, walk to beach!
10.0 out of 10, Exceptional, (20)
"Very clean! Perfect location- walking distance to everything! Beach, restaurants, shops! Would definitely stay again!"
DeweyBeach 2BR Ground Floor Condo. Family-Friendly, quiet, clean, walk to beach!
Come see beautiful fall sunsets over the bay! Amazing off season rates!
10.0 out of 10, Exceptional, (115)
"Went to a wedding in Dewey Beach and stayed the weekend. Very nice property very nice location."
Come see beautiful fall sunsets over the bay! Amazing off season rates!
Newly Renovated Dewey Beach Cottage, 150 Yds from the Beach, Private Beach!!
9.8 out of 10, Exceptional, (18)
"Great location, space is large and great for entertaining and the backyard is awesome. The process of having to wash the sheets, empty the dishwasher, waiting for washing process to finish in order to get sheets for next customer was absurd."
Newly Renovated Dewey Beach Cottage, 150 Yds from the Beach, Private Beach!!
Sandy Paws Beach House. Pet Friendly! Completely renovated in 2024!
9.8 out of 10, Exceptional, (114)
"My family and I had a great time together, close to the beach enjoyed the views. The beds were comfy and the townhouse decorated nicely and very clean. All great!! Hoping to go back "
Sandy Paws Beach House. Pet Friendly! Completely renovated in 2024!
Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!
9.8 out of 10, Exceptional, (47)
"Beautiful views all day long, wonderful waking up with a coffee over looking the bay and even better ending the day watching the sunset with an adult beverage. The place was fantastic and my wife and I loved it, thank you so much! "
Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!
Luxury 6BR-5.5BA, heated pool, firepit, 2 porches, sheets/twls, beach/baby gear
10.0 out of 10, Exceptional, (69)
"Very nicely appointed and clean. We enjoyed the pool in particular. The landlord communicated with us efficiently and effectively. Highly recommended"
Luxury 6BR-5.5BA, heated pool, firepit, 2 porches, sheets/twls, beach/baby gear
Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!
10.0 out of 10, Exceptional, (44)
"Enjoyed the house very, very, very much!"
Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!
Beach Retreat Located in the Heart of Dewey!
9.4 out of 10, Exceptional, (90)
"This was our second trip here because of the fantastic walk-to-everywhere location. Plenty of room for 3 friends, and we will be back soon! Just a note for improvement: The mattresses need an upgrade and there is general deferred maintenance. But overall, this is a super value for the price. Thanks Gaysha!"
Beach Retreat Located in the Heart of Dewey!
OCEAN FRONT Pet-Friendly Downtown Dewey Beach 2BR Townhouse!
9.6 out of 10, Exceptional, (21)
"Great location on beach and near restaurants. Nice view from the upper deck."
OCEAN FRONT Pet-Friendly Downtown Dewey Beach 2BR Townhouse!
Waterfront Retreat on Private Beach w/ large Boat Dock - Breathtaking Sunsets
9.8 out of 10, Exceptional, (97)
"I have stayed at many locations in Dewey and this is still my favorite spot. Great location, great view, has everything you could ever need in a rental. Highly recommend!!"
Waterfront Retreat on Private Beach w/ large Boat Dock - Breathtaking Sunsets
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.
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Other types of properties in Dewey Beach you may be interested in

Surf Club Oceanfront Hotel
2.0 star property
9.0 out of 10, Wonderful, (1003)
"Beautiful stay, gorgeous ocean views. Can’t beat it!!"
The price is AU$129
includes taxes & fees
23 Nov - 24 Nov
Surf Club Oceanfront Hotel
Gold Leaf Hotel of Dewey - Rehoboth Beach
2.5 star property
8.4 out of 10, Very good, (1002)
"Excellent all around, thanks."
The price is AU$89
includes taxes & fees
1 Dec - 2 Dec
Gold Leaf Hotel of Dewey - Rehoboth Beach
Hyatt Place Dewey Beach
3.0 star property
8.8 out of 10, Excellent, (1000)
" Very nice and welcoming!! "
The price is AU$183
includes taxes & fees
17 Dec - 18 Dec
Hyatt Place Dewey Beach
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

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Frequently asked questions

Can I find a holiday rental in Dewey Beach?

Yes, there are holiday rentals in Dewey Beach close to Dewey Beach Parasail, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Dewey Beach speak positively about the popular beaches and top-notch restaurants in this destination. Give yourself some extra time to check out the shops and bars during your trip.

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

Gorgeous PENTHOUSE Sea Watch 1919 Incredible Views Amenties: This holiday home rental outside of Dewey Beach offers an outdoor pool, a pool table and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 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 Dewey Beach?

Expedia has 220 holiday rentals for your stay in Dewey Beach.

What can I see and do in Dewey Beach?

Family-friendly attractions include Dewey Beach Parasail and East of Maui, whereas Dewey Beach and Delaware Seashore State Park are a couple of great spots to enjoy the outdoors. While here, Bottle & Cork and Indian Beach are other places worth a visit.

What are holiday rentals like in Dewey Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dewey Beach. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip.