Holiday rentals with a pool in Chincoteague Bay

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Popular amenities for Chincoteague Bay rentals with a pool

House rentals with a pool

Guest favourite
Home in Montross
4.98 out of 5 average rating, 107 reviews

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit

BrittanyRating, 5 stars2 weeks ago
Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!
Superhost
Home in Montross
4.92 out of 5 average rating, 208 reviews

The Glebe

KristinaRating, 5 stars3 weeks ago
We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!
Guest favourite
Home in Berlin
4.79 out of 5 average rating, 195 reviews

OC MD trip bayside, great amenities

SandraRating, 5 stars3 days ago
I arrived after dark, on a Friday, so I was thinking I’d have some challenge to find the house. I was wrong! There was a guard at the gate who was quite friendly and helpful, gave me the parking pass for my stay and a map with outlined directions to find the street and the house. I found it first time through. Keys were in the lockbox, instructions were clear and the gate pass card was in the dish on the table. I had a lovely quiet night in a very comfortable bed with no noise or distractions. After a 10 hour drive I needed that! In the morning I had a small convenience issue, which Terri and Shawn were immediately responsive to, offered me a self service solution which worked fabulously and I had no other problems during my stay for a total of 8 nights. I especially loved the water pressure in the shower! Love that the house is a short hop from both OC and Assateague! I would definitely stay here again!
Top Guest favourite
Home in Villas
4.99 out of 5 average rating, 132 reviews

Hot Tub Backyard Oasis, Private Beach, Local Pool

SeanRating, 5 stars6 days ago
We absolutely loved this house! Heather and Andrew were fantastic hosts friendly, responsive, and helpful. They answered all of our questions promptly and gave an excellent recommendations. The outdoor space was great and it helped to keep the kids entertained even when the weather didn’t cooperate. The house itself was spotless, well maintained, and felt very welcoming. We would definitely stay here again and highly recommend it to anyone looking for a relaxing and family friendly beach getaway!
Guest favourite
Home in Montross
4.99 out of 5 average rating, 156 reviews

Beach Please! River cottage w/private beach & dock

LisaRating, 5 stars2 weeks ago
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.
Superhost
Home in Berlin
4.8 out of 5 average rating, 110 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

PaulRating, 5 stars6 months ago
Stayed for the weekend after Thanksgiving and it was a great experience. The house was cozy, the beds were comfortable, and the bathroom shower was awesome. The best part of the house is the view out over the bay. It’s really peaceful and a great spot to have coffee and watch the sunrise. We will definitely stay here again!
Top Guest favourite
Home in North Cape May
4.99 out of 5 average rating, 209 reviews

The Villa By the Bay-Private Heated Pool & Hot Tub

MiriamRating, 5 stars2 weeks ago
We had a wonderful stay at this North Cape May home. The house was spotless when we arrived and well equipped-perfect for our group of 6 adults and a baby. The heated pool and hot tub were great extras and we enjoyed them both. The owners went above and beyond by providing snacks and toiletries. While not in downtown Cape May, the location was very convenient- just 10 minutes to town and extremely close (walking distance) to a grocery store and other shopping. The owners were extremely responsive and helpful throughout. I highly recommend!
Top Guest favourite
Home in Lusby
5 out of 5 average rating, 141 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

LaurenRating, 5 stars1 week ago
I recently hosted my wedding at Rousby Hall, and it was truly the most unforgettable experience. The grounds are absolutely stunning — from the waterfront views to the beautifully maintained gardens, every corner felt like a dream. The historic home itself is full of charm and elegance, offering the perfect backdrop for both our ceremony and celebration. Polly, the host, went above and beyond throughout the entire process. She was incredibly helpful, kind, and responsive, which made planning feel effortless. Her knowledge of the property and attention to detail ensured everything went smoothly. I can’t imagine a more perfect venue or a better person to work with. Rousby Hall gave us memories that will last a lifetime, and we’re already talking about returning for future celebrations. If you’re considering this venue — do it! You will not regret it.

Condo rentals with a pool

Guest favourite
Condo in Ocean City
4.98 out of 5 average rating, 41 reviews

Charming Northside Park Condo w Pool, Walk 2 Beach

AndyRating, 5 stars1 month ago
Julie's condo is very cozy and welcoming. It's a wonderful place for a weekend or a longer vacation. Julie was very responsive and proactive anytime my wife and I had any questions. Plenty of recommendations were provided to us so we could better plan our time in Ocean. Thank you so much, Julie! We'll be back again!
Top Guest favourite
Condo in Ocean City
5 out of 5 average rating, 39 reviews

Luxury Oceanfront Getaway!

ChristopherRating, 5 stars1 week ago
Shiri's place was perfect. My wife and I have both frequented OC since we were kids, and we both agreed that this was the nicest place we have ever stayed. Far enough from the boardwalk to be peaceful, close enough to travel to the boardwalk if we wanted. The condo was clean, there is a washer and dryer in the unit which is a plus, and a tv in both the living room and bedroom, which is something we always look for. There is plenty to do in the area! Unfortunately, it rained during our whole stay, but you have beach access just outside of the building! We are excited to stay at Shiri's place again (hopefully when it's not raining 😂) and spend some time on the beach! We sat on the balcony every morning and night and it was so peaceful. Shiri was always very helpful and kind - she is such a wonderful host!
Guest favourite
Condo in Ocean City
4.91 out of 5 average rating, 310 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

JasonRating, 5 stars1 month ago
Great place to stay in Ocean City! clean and wonderful place situated right off the beach secluded and quiet. had lots of beach materials for use. would stay again.
Superhost
Condo in Ocean City
5 out of 5 average rating, 4 reviews

New Updated Direct Oceanfront Condo - Pool & Wifi!

KaraRating, 5 stars2 weeks ago
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!
Top Guest favourite
Condo in Ocean City
5 out of 5 average rating, 44 reviews

Top Rated! Beautful Sunsets! Midtown Bayside Condo

LandonRating, 5 stars2 weeks ago
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!
Guest favourite
Condo in Ocean City
4.93 out of 5 average rating, 14 reviews

Extraordinary Oceanfront Penthouse | Unit 1210

HopeRating, 5 stars3 days ago
Wonderful, updated top-floor condo. Everything was as pictured- you won’t be disappointed. Great balcony view/furniture. Updated appliances. Great showers- strong water pressure. Higher end of rental cost in the area, but well worth it. Easy quick beach access- not overly crowded.
Superhost
Condo in Ocean City
4.83 out of 5 average rating, 281 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

ErinRating, 5 stars2 days ago
We had a fantastic stay at Adam’s place. Location was amazing and the description of the unit was exactly on point. Place was clean and comfortable and even had some toys and games for the kiddos! Great communication with the host and we’ll definitely be back!!
Superhost
Condo in Ocean City
4.87 out of 5 average rating, 78 reviews

Oceanview Oasis with 2 private balconies

AmyRating, 5 stars6 days ago
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!!

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