Cottage holiday rentals in Dewey Beach

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Popular amenities for Dewey Beach cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Bethany Beach
4.94 out of 5 average rating, 17 reviews

Bethany Beach Sea Colony Canalside Sleeps 7

JosephRating, 5 stars4 months ago
We enjoyed Kristen’s home it was so he perfect location for our itinerary on this adventure. Blessings - joe and Jen
Top Guest favourite
Cottage in Dewey Beach
4.89 out of 5 average rating, 81 reviews

Uncle Buck's

BreezyRating, 5 stars1 month ago
My friend and I loved staying at this little house. It was so close to the beach, the hot tub was amazing in the evenings and the house was comfortable and welcoming. It was clean, organized and well stocked with the towels. Great little getaway spot at a wonderful price.
Guest favourite
Cottage in Bethany Beach
5 out of 5 average rating, 5 reviews

2br | 2 bath. tennis, pool, hot tub, 0.5m to beach

KathrynRating, 5 stars10 months ago
Our stay was great! The house was perfect size and had everything we need for a great beach trip. Just a short drive (or tram ride) to the beach and some great places within walking distance. We felt right at home. Gannon was extremely responsive, friendly, and a great host.
Guest favourite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 173 reviews

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

BeatriceRating, 5 stars1 week ago
This was our second time staying at JoJo’s cottage and it was another amazing experience! The house really makes you feel like you’re right at home. The kitchen is well stocked, so we were able to do a lot of cooking at the house. But you’re also so close to so many restaurants for when you’re feeling something easier! It really is a perfect spot, especially if you have dogs and/or kiddos. We would totally book again next summer 😊
Superhost
Cottage in Lewes

Lewes beach family cottage

YevhenRating, 5 stars11 months ago
We were the very first guests in Eric’s house and we thought Eric did a good job to prepare for his first guests. There are still a few things to improve but I’m sure those will get improved with time. Overall, this is a great house in a very quiet neighborhood. Only a few miles away from the beach. There is a full size on the ground pool that is pretty new and it was a nice surprise especially for kids. Kitchen has everything you need and maybe more. We’ve had a few issues in the beginning but Eric was real quick to respond and help resolve the issues. Additionally, he was checking in sporadically through our stay to make sure everything was going well. We thought it was a good value for a house in Lewes during very busy season. I would recommend anyone looking for a stay in Lewes to give this house a chance.
Cottage in Newark
4.89 out of 5 average rating, 54 reviews

Cropper Creek House

CharlotteRating, 5 stars72 months ago
The house is spacious, clean, and conveniently located. Laura made everything simple, including easy check-in and good local tips. It was perfect and fun for four, but would comfortably accommodate more!
Private room in Rehoboth
4.6 out of 5 average rating, 5 reviews

Beach Suite 2 King Beds Pet Friendly Canalside Inn

AdeleRating, 5 stars40 months ago
Had a great couple of days here with our outsized chocolate lab! Everything you would need is provided including a friendly welcome!
Guest favourite
Cottage in Selbyville
4.88 out of 5 average rating, 41 reviews

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV

PaulRating, 5 stars2 weeks ago
My family and I rented the house for a long weekend in early summer. We loved the privacy and the nature around the property literally had deer grazing around the house all of the time. The neighborhood is very good for walking. Close drive to Ocean City, Maryland plenty of restaurants and entertainment. We would definitely return.

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Ocean Pines
4.98 out of 5 average rating, 41 reviews

3-bedroom cottage in Ocean Pines

SylvainRating, 5 stars3 weeks ago
Viktoria's place was exactly what we were looking for. A three-bedroom place not far from Ocean City and Assateague, in a peaceful environment. Was super easy to go to both places during the long Week-End. The house was as advertised, spacious enough to accommodate the family but not too big. Next time we plan another WE in this area, we will certainly Viktoria's place again.
Guest favourite
Cottage in Lewes
4.95 out of 5 average rating, 73 reviews

Dog Friendly Fenced In Backyard Cozy Home

LouisRating, 5 stars5 days ago
The location is about 15 minutes to Rehoboth Beach so it is perfect. The house was clean and peaceful. The yard was great for our three dogs. My son and wife were also very happy about the space. We really enjoyed it and would definitely stay again.
Top Guest favourite
Cottage in Ocean City
4.99 out of 5 average rating, 70 reviews

WalkToTheBeach! FirePit-PingPng-N64-FencdYrd-Bikes

ShontayRating, 5 stars1 month ago
My family enjoyed our stay at the Blue House for a weekend getaway! The Host, Neil, allowed us to check in early, which was very much appreciated. The parking is right in front of the house. The check in was easy, after we realized you have to go through the back to access the entry door. The home was clean and we were very comfortable in it, especially the beds. I was able to prepare several meals and my husband prepared some bbq on the grill one evening. There are 5 bikes available, but only my younger son and I rode 2 of them around the neighborhood. The beach is only a few blocks away and easily assessible. I wanted to play ping pong, but couldn't figure out how to set up the table net lol. The host was very responsive and regularly reached out to make sure we were ok. He event sent us over some of the most delicious, warm donuts one morning. Overall, our experience was exceptional and we would love to stay there again next time we visit Ocean City!
Guest favourite
Cottage in Lewes
4.87 out of 5 average rating, 201 reviews

BnB’s Dog-Friendly Cottage

SydneyRating, 5 stars2 months ago
Jacki's home was so lovely and perfect for a weekend getaway with some friends. We brought our dog who absolutely loved the fenced-in yard and extra loved the mountain of toys stocked in the house!
Superhost
Cottage in Milton
4.82 out of 5 average rating, 77 reviews

Bayshore Cottage, Steps to the beach!!

MariahRating, 5 stars3 weeks ago
Great, quiet location if that’s what you are looking for, which we were! Extremely close to the beach too! Beach was quiet and relaxing. It’s about a 20 minute drive to most restaurants, but it’s a beautiful drive through Prime Hook Sanctuary:))
Guest favourite
Cottage in Ocean View
4.9 out of 5 average rating, 20 reviews

Monthly Rental w/ TONS of Storage! Please message

SueRating, 5 stars9 months ago
We had a very nice stay. Everything was very clean and nicely appointed. Our two doodles loved it too. Will is a very gracious host and we highly recommend him and his properties anytime you want to come to the Bethany beach area. We will be coming back very soon. Thank you.
Superhost
Cottage in Ocean View
4.77 out of 5 average rating, 53 reviews

OV Central Beach Cottage

FrankRating, 5 stars9 months ago
The house was exactly as seen on website would definitely stay again..definitely longer just to have a bbq and fire 🔥 easy to get to town..very quiet felt like home .i live in the woods in the hudson valley already showed my friends and family house 🏠 thank you so much 💓
Guest favourite
Cottage in Rehoboth Beach
4.97 out of 5 average rating, 86 reviews

Cozy Cottage Close to Downtown Built in 2021

AaronRating, 5 stars5 days ago
Very much enjoyed our stay at the Cottage! Place was even nicer than the pictures showed and there were a lot of thoughtful extras for our kids as well. Would definitely stay there again!

Private cottage rentals

Top Guest favourite
Cottage in Ocean Pines
4.96 out of 5 average rating, 28 reviews

Cozy Cottage near the Ocean and Wild Horses

VivienneRating, 5 stars9 months ago
House was very clean and cozy. Everything is labeled and easy to find and Anne was very responsive with questions l had. The location is quiet and great for walking or bike riding. Restaurants are super close and so is the grocery store. Beach and other cute towns such as Berlin and Snow Hill are very easy to get to as well. We had a wonderful time staying at Anne's place.
Guest favourite
Cottage in Ocean Pines
4.93 out of 5 average rating, 46 reviews

Rhapsody in Blue Beach Cottage Ocean Pines, OC MD

WilliamRating, 5 stars1 month ago
Everything you would need! Linens, coffee, all kitchen utensils and appliances. Easy entry. Super cool AC! Nice quiet neighborhood. Clean and cozy. Very happy. Thank you!
Top Guest favourite
Cottage in Cape May
4.98 out of 5 average rating, 55 reviews

Cape May Carriage House

EricaRating, 5 stars1 week ago
Shannon’s place is PERFECT. We are a small family of 4, (2 year old and newborn), and this place had everything we needed to have a long weekend. We could only stay 24 Hr due to a health complication, but we truly hope to be back next summer. The yard is stunning and the back porch is perfect. The little play kitchen was such a nice touch that it kept our 2 year old busy right away while we unpacked. If you’re looking for a stress free vacation in a home that has it all, Shannon’s home is it! You can tell she truly thought of every detail in this home. See you next year :)
Superhost
Cottage in Ocean City
4.65 out of 5 average rating, 65 reviews

Captain’s Hill Cottage - Ocean City

TriciaRating, 5 stars8 months ago
The house was as described. Cozy and comfy with a nice, big yard and quiet surroundings. Aaron was totally responsive and went above and beyond to accommodate us and our dog, Gumbo. Definitely recommend him as a host and his place if you want a quiet place in West Ocean City.
Superhost
Cottage in Frankford
5 out of 5 average rating, 4 reviews

5 Miles to Beach Quiet Secluded 3 Bedroom Cottage

LilRating, 5 stars21 months ago
What a great house and location for our beach trip! The little boys played in the sand mound before and after each beach day! The outdoor shower is amazing, not rough and ugly like some. The back porch is a perfect place to land! We had everything we needed in the kitchen to have nice family dinners and relax at home in the evening. We had a blessed beach vacation at The Little Beach Cottage!
Guest favourite
Cottage in Berlin
4.93 out of 5 average rating, 92 reviews

Quiet Retreat near Assateague Island

DeniseRating, 5 stars9 months ago
This was our second trip to Catherine's retreat and we loved our stay this time even more than our first. Both Catherine and her husband assisted us when we had questions and provided suggestions for local events. The property is such a restful delight; from the pool, the views of the marshes, the quiet, and the plethora of wildlife to see. The home is comfy and we had everything we needed to make ourselves great meals and just soothe the soul. Between spending time on Assateague by day and returning to this special place at night, we came home restored. Thanks again!
Superhost
Cottage in Berlin
4.8 out of 5 average rating, 10 reviews

Immaculate 2 Bedroom Cottage

EricRating, 5 stars8 months ago
What a great stay in Ocean City! Robert couldn’t have been more responsive and the space was better than advertised. So many amenities provided - it felt like we were at home! Highly recommended - we will be booking again on our next trip to the OC.
Guest favourite
Cottage in Ocean Pines
4.85 out of 5 average rating, 55 reviews

Charming Canal Front Cottage

TomRating, 5 stars3 weeks ago
The pictures do not do justice for this rental. I have been staying in Ocean Pines for years now, this is by far the nicest place we stayed at. Colleen was great with communication before arriving and when leaving. The house is right along the canal in Ocean Pines. This is where "everyone wants to be" when staying in Ocean City. The house was clean, nice large deck and closed in porch to relax during the evenings. Honestly, I can't say enough about this rental. If you are not sure about renting, take it from me, you will not regret this find!

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