
Holiday rentals with a pool in Worcester County
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Top-rated rentals with a pool in Worcester County
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Popular amenities for Worcester County rentals with a pool
House rentals with a pool

Mins to Golf & Beach! Private Pool & Luxe Firepit
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!

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

TwoBlockstoBeach&Boardwalk! Pool! PingPong! Bikes!
This home was perfect for our family getaway! Shawn was an excellent host! The home had great amenities and things for our family to do! We really appreciated the beach gear, chairs, wagon, pool toys and games. You can tell Shawn put a lot of thought into this home and what it has to offer to its guests. We recommend this home for sure! Beautiful home!

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach
The host was so accommodating and respectful! always responded quickly! Location was perfect for where our family needed to be! Host allowed us to checkin early on day of arrival after very long trip! Excellent, and beautiful property! Thank you so much!

Little house in Berlin, Md.
Great for a few days getaway! Comfortable and cozy!

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room
The Oasis was perfect for our needs . We will definitely book it again in the future!

Beautiful Cottage W/ shared pool & close 2 beach
Everything was as described. Jennifer was very responsive and left excellent instructions on everything. We will stay there again.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
My family really enjoyed our stay here. The house was so quaint, clean, well stocked, and all on one floor. There was plenty of space for my multi-generational family. Also, the beaches and other area attractions were nearby (just a short drive). I’d definitely recommend staying here!
Apartment rentals with a pool

Steps from Seacrets Beach House Getaway
Andrew could not have been a better host. He was especially responsive even when were checking in late. It was truly a great experience

New Updated Direct Oceanfront Condo - Pool & Wifi!
Listing is better than you think it is! Great location (I was nervous about it because we usually stay closer to 120th St) it was very private and peaceful. Big bonus that it is right over the bridge (no extra traffic lights!) The kitchen is fully stocked - we wound up bringing a lot that we didn’t need. The pullout couch is also one of the most comfortable I’ve ever been on. Beautifully decorated and updated. Might book again this season!

Cozy 1 BR Condo - 5 Minute walk to Beach, w/ Pool!
Our stay was very peaceful and relaxing all thanks to Clint’s place! We were able to walk to the boardwalk and restaurants. The place itself was clean and has everything you would need on vacation. Thank you Clint!

Top Rated! Beautful Sunsets! Midtown Bayside Condo
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!

Oceanview Oasis with 2 private balconies
Beautiful place with the best views!!! Great area. The pool was awesome and heated most days and with the cold/cloudy days we had, that was a treat especially for my daughter. It was never busy or crowded and had very friendly staff. All VERY nice families/couples stayed here- no noise or ruckus at night. Julie was responsive and quick. My only “concern” Would be no screen door on deck but luckily we didn’t get many flies/birds up that high (14th floor). Still I would have loved to sleep with the sliding door open listening to the ocean. It had two bed rooms and all was decorated nicely. We had such a GREAT time and absolutely LOVED Fountainhead and would definitely stay again!!

The Coastal Condo
We loved our stay at The Marylander in Colleen & Joe’s condo. From the very start she was very responsive, understanding and kind. The condo was the perfect amount of space which was well cared for & clean, we enjoyed the amenities that came with the building and the short walk to the beach! I’m already looking forward to booking another stay here!

Prime Condo North OC 2 Blocks to Beach w/ Pool
Place was great to stay at ! Very nice host and clear instructions. 10/10 👍🏽

127th Bayside-pool-short walk 2 beach-By Park!
Erin was super easy to talk to and responded right away to any questions I had. She gave clear directions upon check-in and check out and her place was super clean and comfortable. We found a really cool Mexican restaurant located in the shopping complex beside the condo which had really great margaritas and tacos. We would definitely stay here again!
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Towers Beach
- Northside Park
- Assateague Beach
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Poodle Beach
- Delaware Seashore State Park
- Snead Beach
- Peninsula Golf & Country Club
- Plantation Lakes Golf and Country Club
- Heritage Shores
- Gerry Boyle Park
- Baywood Greens Golf Maintenance
- Bear Trap Dunes
- Whiskey Beach
- Nassau Valley Vineyards
- Wallops Beach
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