
House holiday rentals in Chincoteague Bay
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Top-rated house rentals in Chincoteague Bay
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Popular amenities for house rentals in Chincoteague Bay
House rentals with a pool

Waterfront | Kayak+Beaches+Pool | Gameroom+Firepit
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!

The Glebe
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!

OC MD trip bayside, great amenities
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!

Hot Tub Backyard Oasis, Private Beach, Local Pool
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!

Beach Please! River cottage w/private beach & dock
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

Mosaic Life Escapes -Bayfront Million Dollar Views
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!

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

Historic Rousby Hall, Waterfront, Pool, Beach
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.
Weekly house rentals

Oysterhaven Cottage
very good communication, some beach gear available at the house which we were happy to have. location is quiet and about 3/4 mile to shops and restaurants. bring bikes or scooters for this island.

The Cottage Bluefish -new in '24
We loved our stay at The Bluefish! The home was beautifully renovated, extremely clean and felt so welcoming. The location was ideal—just a quick walk to Main Street and the Island Creamery (a non-negotiable stop!). Jennifer was an exceptional host, always quick to respond and so helpful throughout our stay.

Strathmere Beachfront House
We had an excellent stay at Brooke’s place for the second year in a row. The house is exactly as described and in the pictures - beautiful finishes, tasteful and comfortable decor, plentiful amenities. The location couldn’t be better. It’s close enough to all the activities in Ocean City for the family but far enough away that it feels remote and peaceful. We used to go to the Outer Banks for many years, and my wife kept commenting on how it felt like we were there but with all the fun the boardwalk close by. Highly recommend staying here!

Amazing 2 Bedroom home close to the beach!
We needed a small place to stay for a few days and this was the perfect place for the two of us; it was cozy, spotless, well equipped for all that we needed and the decor was beachy which was perfect for the area. Jacob was quick and attentive to any question we had - it was so quiet and peaceful outside. It was a perfect getaway for us - we would highly recommend to anyone needing a nice, quiet place in the future. Thank you!!!

Bikes-Kayaks-Outdoor Shower Grill-Firepit-Beach Eq
This place had a great location; it was less than 10 minutes for the local restaurants and only a 15 drive to the beach. The kitchen had everything you needed, there was plenty of space for atleast 6 people (even though there was just the two of us). The airbnb itself was really charming. Host was amazing, really responsive and communicative. Their checkin and checkout procedures were really clear. My only “asterisk” is that since it is an older house and in the middle of a marshland basically, it was pretty humid inside. It seems normal for the area especially considering it was raining half of our stay. The AC boxes in every room definitely helped but just something to note about our stay. I’d recommend a dehumidifier to the hosts. Overall a great stay, would recommend this place to all when staying in Chincoteague!!

Private Country Beach Retreat
Kristy’s place was so peaceful! If you are looking for a quiet space then this is the place for you! Everything from the location to the details in the home curated a calm environment. And if you need to hear a little noise Cape Charles is just a drive away! Also check out the lovely Chatham vineyard just down the road!

Central Location- Walk to Dining & Entertainment!
We had a great time at the Reel Deal on Teal. The place was adorable, beautifully decorated, and cozy. He provided everything, and I mean everything you could possibly need. Kitchen is expertly stocked and allowed us to cook a few meals. The location was right in the middle of everything. Chip was an excellent host and had great recommendations for restaurants and things to do. He even provided a park pass to see the ponies, which was much appreciated. We would highly recommend this place to anyone looking for a relaxing getaway.

Egret’s Point on the Creek
Everything was AWESOME! Very homey, clean, great location. They had everything and even more than we needed! When we return if we need somewhere to stay and Egrets is available we will definitely book again!
Private house rentals

Sunnybank Getaway - Waterfront w/Pier & Kayaks
We love our stay here! The house had everything we needed and more. It was easy to find, and the views were amazing. We spent the whole time outside in the nature, and we loved how quiet it was. Kevin was easy to reach for any questions we had, and we appreciated his help. We would definitely come back here in the future.

Ocean Pines 2BR 1BA Cottage with Fire Pit
Our family has a beach house in Ocean Pines, and we are looking to purchase our own in the coming years. We have stayed in all parts of ocean Pines and love it so much, we came across this house a couple months ago and I’m so glad we did! We spend most of the summer in Ocean Pines had different rentals and will definitely be coming back specifically to this one!! it’s perfect for our small family and pet friendly! The house was small but spacious, quiet and tranquil. 10/10 highly recommend!

Riverfront Retreat-Kayaking/Fishing/Nearby Beaches
Comfortable accommodations in a beautiful, peaceful spot to enjoy with family. Loved looking out the windows at the Pocomoke River at different times of the day and night! :-)

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed
Cozy little beach spot. Shelly was so responsive and helpful! Would highly recommend!

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room
We cannot say enough good things about this home. It had everything we could have wished for! Our family of 11 enjoyed every moment and wished we didn’t have to leave. The house was immaculate. The host (Caleb) was so quick to respond to our messages and even popped by to help us figure out the surround sound one evening. We cooked and ate every meal at the house and had all kinds of things to do just minutes from the house (disc golf, golf, pickle ball, a zoo, shopping). We even decided to forego our plans to go to the beach because why would we go when they have their amazing private pool. We were entertained from morning to night with all the games and surround sound movie room. There was NOTHING we didn’t love about this home. Thank you, Glen and Caleb! I would give you 10 stars if I could!

The Haven On The Chesapeake Bay
The Haven was truly a gem. It was so private and secluded- just what we needed to relax and reset. Ashley was so friendly and provided so many helpful accommodations that you’d typically not find elsewhere, such as complimentary coffee and a stocked s'mores station. Collectively, I think my family most enjoyed using the kayaks and paddle boards to explore the bay everyday. The kids absolutely loved hunting for wildlife around the house and pond. I’ll never forget this trip!

Luxe Lewes Carriage House: Spa Hot Tub/Estate Pool
Let's see...if Martha Stewart had a rental cottage, it would look just like Lisa and Jay's carriage house. Everything from the splendid charcuterie board and Prosecco on ice that awaited us upon our arrival to the beautifully designed cottage and wonderful gardens helped create an amazing vacation that we will not forget anytime soon. Jay and Lisa truly paid attention to every detail right down to the perfectly placed English antiques, fresh cut flowers and towels so thick you could drown in them. Nothing was missing and their hospitality made you feel right at home. We had smiles on our face the entire time! This is now my new Happy place. The gold standard by which every rental will be judged....perfect hosts, perfect place..like I said...Martha Stewart. Thank you Lisa and Jay for making our stay a wonderful experience!! We will definitely be back to your Lewes Carriage House whenever possible!

Pelican Sunset - Waterfront With Pier
We loved watching the sunset and the dolphins from the beautiful private dock. The deck upstairs was perfect for stargazing. The beds were comfortable and the house was adorable. Chincoteague is super cute with plenty of shopping, restaurants, and natural beauty.
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