House holiday rentals in Ocean Pines

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Popular amenities for house rentals in Ocean Pines

House rentals with a pool

Guest favourite
Home in Ocean Pines
5 out of 5 average rating, 21 reviews

Salty Serenity

MiaRating, 5 stars2 weeks ago
Lovely home with great character and countless amenities. Such a perfect location! House was pretty clean and exactly as described. All the amenities were great, the backyard was incredible with a grill, fire pit, fairy lights, and screen-in-porch. Great for family or friends, would stay again! Accommodated our group incredibly well!
Guest favourite
Home in Montego Bay
4.95 out of 5 average rating, 255 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

ErikaRating, 5 stars3 weeks ago
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!
Guest favourite
Home in Berlin
4.79 out of 5 average rating, 194 reviews

OC MD trip bayside, great amenities

CalistaRating, 5 stars1 month ago
Absolutely wonderful hosts!! Very responsive and helpful. There might have been an issue with the lockbox so they called ahead to make sure we could get in! I will definitely be booking with Shawn and Terri again!
Guest favourite
Home in Ocean Pines
4.94 out of 5 average rating, 52 reviews

Close to OC, Family Friendly, Pool Access

TanieshaRating, 5 stars1 week ago
This was my very first time using an airbnb and Beth set the bar high! I honestly don't know if i could ever stay in a plan old hotel room ever again. She was helpful and responsive from the day we made the reservation all the way through and including our checkout. Beth created a welcome package that made acclimating to her home a breeze. Her house was clean, organized and stocked with all the essentials. What was advertised in the photos and description is exactly what was provided. She even had a wide variety of games to play! As far as location, it was just the right distance away from the hustle and bustle of the beach. We were able to go enjoy our day and then return to the quiet and peacefulness of her home to get a good night's sleep. Her home was also convenient to shopping within 15 minutes of driving. Checkout was easy and without a housekeeping cart sitting in the hallway, I didn’t feel rushed. So if you're planning to visit OC, Beth's house is right for you.
Guest favourite
Home in Ocean Pines
4.85 out of 5 average rating, 20 reviews

Ocean City (OC) Beach Retreat

DesireeRating, 5 stars3 days ago
The home had a welcoming, comfortable feel. Beautiful inside and out. Private peaceful neighborhood. The home was well equiped with what you would need. Do was a friendly, kind and responsive host. Do was very quick to respond to our questions/concerns. Will definitley stay again.
Superhost
Home in Ocean Pines
4.86 out of 5 average rating, 50 reviews

Entire Home w King Bed in Peaceful OceanPines 🌊🌲

JordanRating, 5 stars6 months ago
This was our second stay at this beautiful home that was perfect for my family to celebrate Thanksgiving! Fantastic location, 15 min to the beach, restaurants and stores a few minutes away, everything we needed if we forgot anything or didn’t feel like cooking. The beds were super comfortable and the open floor plan was perfect our family to hang out!
Guest favourite
Home in Ocean Pines
4.97 out of 5 average rating, 32 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

JeffRating, 5 stars1 month ago
Fantastic place and host! Will definitely stay there again!
Top guest favourite
Home in Ocean Pines
5 out of 5 average rating, 55 reviews

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

TanyaRating, 5 stars2 weeks ago
My family and I had a fantastic experience staying at this home! The home was exactly as described - clean and comfortable. The amenities provided (like the grill, toiletries, board games, Wii, chargers, and Wi-Fi) made it feel like a home away from home. The location was ideal—close to everything I needed and It was easy to get around.  Our host was incredibly responsive, friendly, and accommodating checking in to make sure everything was going smoothly. I would definitely stay here again and recommend it to anyone looking for a relaxing and hassle-free stay.

Weekly house rentals

Top guest favourite
Home in Berlin
4.92 out of 5 average rating, 52 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

PatrickRating, 5 stars1 week ago
This was a great place to get away for some peace and quiet. We had a lacrosse tournament in Berlin and the field was 15 minutes away. Beautiful home and very cozy. Very easy check in and Brenda was very quick to answer any question. Totally worth it!
Top guest favourite
Home in Ocean Pines
4.97 out of 5 average rating, 32 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

DimitrisRating, 5 stars2 weeks ago
My family and I find this place to feel like home. Very clean the host was very responsive to any questions I had prior to the date of the event. The price was just right for all that we received. The place was private with much to do and the surrounding area. I definitely will be coming here when I visit Home again .This place was big enough for my family of eight to enjoy themselves to the fullest. Thank you again.
Guest favourite
Home in Ocean Pines
4.97 out of 5 average rating, 34 reviews

WHAT DAY IS IT???????

KarinRating, 5 stars10 months ago
We had a wonderful stay at Brian’s place! The house was very comfortable, beautiful, clean and well equipped. The welcome basket and the baskets of samples in case you forgot something was a nice touch. He was very responsive to any questions I had. The beach parking pass was perfect - we took advantage of that on 2 days. I would definitely recommend this house. I wish we had more time at the house to enjoy it even more.
Top guest favourite
Home in Ocean Pines
5 out of 5 average rating, 11 reviews

Waterfront Vacation Home in Ocean Pines

CarlosRating, 5 stars1 month ago
Great hosts & beautiful home. Extremely responsive & helpful with anything needed. Some of our guests arrived early & they didn't hesitate to respond to my messages & provide an update check in. Would highly recommend a stay. Beautiful area, great for a golf outing & a lot of good food places around.
Top guest favourite
Home in Ocean City
5 out of 5 average rating, 30 reviews

Direct Ocean Front - Beach Retreat Condo!

AliceRating, 5 stars1 month ago
We had a wonderful stay at Chris and Loreees place! Super responsive when needed and clear instructions for check in and out. Private, quite, clean building and condo and we had everything we needed. The views were stunning & exactly as pictured. Walking distance to many stores, restaurants, and 7-11 next door for convenience. I would recommend staying here!
Guest favourite
Home in Ocean Pines
4.91 out of 5 average rating, 23 reviews

Cottage in the Pines

WillaRating, 5 stars1 week ago
I had a wonderful stay! The property was exactly as described—clean, comfortable, and beautifully maintained. The host was incredibly friendly and attentive, making sure everything was perfect throughout my visit. The neighborhood was charming and conveniently located, with plenty of great restaurants and shops nearby. I highly recommend this Airbnb to anyone looking for a relaxing and enjoyable experience. I would definitely stay here again!
Top guest favourite
Home in Ocean Pines
4.86 out of 5 average rating, 29 reviews

Serene OP cottage perfect for your next getaway!

AllyyRating, 5 stars8 months ago
Jessica was very helpful and pleasant to communicate with. We came down for a concert series and did not want to stay right in the beach. Jessica’s place was the perfect ride away but perfect for us, quiet and peaceful. Thank you Jessica!
Guest favourite
Home in Ocean Pines
4.93 out of 5 average rating, 44 reviews

Charming Home in a Beach Town Community!

ErinRating, 5 stars10 months ago
Ocean Pines is the perfect location- 20 minutes from the beach and lots of activities in Ocean City but a nice quiet and peaceful place to come back to to relax and enjoy the night with family. This house was a great size with really nice showers and plenty of space. We got the resident rate to visit the Ocean Pines pools which was very nice.

Private house rentals

Superhost
Home in Ocean Pines
4.7 out of 5 average rating, 10 reviews

Cozy Home near OC & Assateague Park

LarryRating, 5 stars1 week ago
Very cozy very peaceful and a nice place to spend on vacation with family and have a good time.
Superhost
Home in Berlin
5 out of 5 average rating, 4 reviews

Mins to Golf & Beach! Private Pool & Luxe Firepit

CaroleRating, 5 stars3 weeks ago
Lindsay and Andrew’s Summer Breeze home in Berlin met all of our expectations. We particularly enjoyed the pool, grill and outdoor amenities - which made it perfect for our family holiday weekend getaway. The house is well kept, comfortable, neatly stocked with all essential amenities as described and, is staged and modeled exactly as pictured in the photos. We appreciated a quiet retreat, off the beaten path, yet we had an easy and quick drive to stores, restaurants and to the Ocean City boardwalk. As hosts, they were very responsive and efficiently communicated what we needed to know in advance, making our stay easy and smooth. From the booking process to assisting us with a couple of adjustments, they did not hesitate to help us. If there is an opportunity for us in the future, we’d love to stay again. Thank you Lindsey and Andrew!
Top guest favourite
Home in Berlin
5 out of 5 average rating, 27 reviews

Cozy, Private Beach home

AshleyRating, 5 stars2 weeks ago
Pamela is very hospitable! Friendly. Commutative. Her home is beautiful and you can tell she thinks of the little things. There was a small container of scrunchies in the bathroom (us women know the scrunchi struggle!). The house is squeaky clean, and we didn’t need to purchase ANYTHING other than food 🤗 which my family really appreciated! Only thing I will point out is it pitch black surrounding the house/area at night. And possibly could be this time of year or maybe location but there are flies everywhere my goodness! Even the restaurants. If visiting OC for the first time like me, please keep that in the back of your mind lol. This place was a 10/10!!
Guest favourite
Home in Berlin
4.96 out of 5 average rating, 74 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LenoreRating, 5 stars1 month ago
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!
Superhost
Home in Ocean Pines
4.88 out of 5 average rating, 32 reviews

Captivating A-Frame in beautiful, Ocean Pines

DevinRating, 5 stars1 month ago
Overall a great stay! The house was beautiful and in an awesome location. Lots of things provided free of charge, such as toiletries, frozen food, cleaning supplies, and others. These appeared to be leftover from previous tenants, but neatly tucked away. I like that they aren't wasteful with perfectly good supplies. One light in the kitchen appeared to have been turned on while we went out once. the rustic, retro style was a huge hit for us and we're very appreciative of the hospitality for the duration of our stay here!
Guest favourite
Home in Ocean Pines
4.97 out of 5 average rating, 79 reviews

*Catch Me By The Sea*

AliciaRating, 5 stars3 weeks ago
We had a really lovely stay. We appreciated the thoughtful communication and local recommendations. We especially enjoyed the backyard and beach ammenities. Perfect little spot if you're looking to stay outside of the hassle and bussle of OC and in the quaint village of OP. Would highly recommend this spot for anyone looking for a good value in a sweet little town. 🦀
Guest favourite
Home in Ocean Pines
4.91 out of 5 average rating, 53 reviews

Private, pet-friendly, w/game room & new kitchen

MaureenRating, 5 stars4 days ago
Maria, the host was wonderful. Each time I sent a message she responded quickly. Had a beautiful week especially for the beach. Would definitely rent again and other properties owned by Maria. Nothing against the host, Airbnb fee should be less and the cleaning fee is to high
Superhost
Home in Ocean City
4.83 out of 5 average rating, 29 reviews

The Oliver House

LizRating, 5 stars3 weeks ago
Janice’s house was lovely! Great location. It looks just like the pictures. The view from the living room and back deck is stunning. The house was very tidy. Janice communicated well and promptly. The only disappointment was that there is no screen door in the master bedroom, and therefore, I couldn’t enjoy leaving the sliding doors open, which I love to do when staying in a waterfront home. Otherwise, we had a wonderful stay! Would definitely recommend!

Quick stats about house rentals in Ocean Pines

  • Total rentals

    240 properties

  • Nightly prices starting at

    ₹3,462 before taxes and fees

  • Total number of reviews

    6.2K reviews

  • Family-friendly rentals

    230 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    120 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines
  6. House rentals