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Waterfront Sunset Retreat with Swim Spa w/ beach

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

Amenities

At Waterfront Sunset Retreat with Swim Spa w/ beach

This home has everything you will need for a comfortable stay. Guests have access to the entire home and everything the space has to offer which includes:
4 Bedrooms
Sleeps 8
3 Bathrooms
6 Parking Spots
Air Conditioning, Fireplace, Central Heating
Baking Sheet, Blender, Coffee Maker, Pots & Pans, Dishes & Utensils, Dishwasher, Freezer, Kitchen, Microwave, Oven, Refrigerator, Stove, Toaster, Wine Glasses
Linens Provided, Clothes Dryer, Extra Pillows & Blankets, Hangers, Hot Water, Clothing Storage (closet or wardrobe), Washing Machine
Games/Board Games, Television
Ceiling Fans, Dining Table, Private Entrance
Children's Dinnerware, Pack N Play
Hair Conditioner, Hair Dryer, Iron & Board, Shower Gel
Laptop Friendly Workspace, Free Internet
Deck/Patio (uncovered)
Communal Pool
Shampoo

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Guests

The Details

A Bit More About This Property

Oyster Bay Getaway- the Pearl of Kent Island invites you to Indulge in the ultimate waterfront escape. This luxurious 4-bedroom retreat combines refined design with resort-style amenities. Wake up to breathtaking water views from nearly every room, then start your day at the home’s extensive coffee bar, fully equipped for everything from K-cups to freshly ground coffee—perfect for slow mornings with a fresh brew.

 

Designed with comfort and flexibility in mind, the home features a private in-law style suite complete with a kitchenette and a shared Jack-and-Jill bathroom accessible from within the bedroom. The primary king suite offers a private en suite bathroom, while an additional king bedroom on the main floor has a full bath just outside the door. A cozy queen bedroom and two pull-out sleeper sofas provide ample space for larger groups.

 

Unwind in the private heated swim spa, rejuvenate in the sauna, or gather around the indoor fireplace for cozy evenings. The home also features a beautifully designed indoor lounge with a poker table, while the garage has been transformed into a vibrant game room perfect for friendly competition and watching fall football. (Please note that the garage game room is unconditioned).

 

Step outside to your private dock and take in the peaceful surroundings, or enjoy evenings by the fire pit under the stars. The outdoor kitchen and grill area make dining al fresco effortless, whether you're hosting or relaxing with family and friends. Walk over to the Community Access Private Beach directly next door to drop in the kayaks and take a stroll along the Bay, just feet from the house.

 

 

Perfectly suited for groups seeking comfort, entertainment, and an elevated waterfront experience, this home offers a seamless blend of luxury, relaxation, and unforgettable views.

 

The property is also perfect for wedding guests and family groups. We are an easy 15–20 minute drive from Chesapeake Bay Beach Club, Kent Island Resort and Silver Swan Bayside.

 

Perfect for Naval Academy families- Close to USNA / Annapolis events.

 

We do not allow pets due to a medically necessary allergy. We understand that some guests may travel with service or assistance animals. If you plan to do so, please contact us before booking so we can confirm whether we can safely accommodate your stay. Unauthorized pets (that are not service or assistance animals) will result in additional cleaning charges, typically ranging from $300–$1,000 depending on the level of cleaning required. We appreciate your understanding and cooperation.

 

No parties of any kind: A $2500 fee will be applied to any reservations who violate this policy. (small gatherings and family celebrations are allowed w/ host approval)

 

No smoking or vaping on property. A $1000 smoke remediation fee is charged to anyone who violates this policy.

 

For your security and others, there are exterior security cameras at front door and garage door and on the dock.

Why our guests

LOVE STAYING HERE

My college girlfriends and I have been taking a long weekend trip together for over 30 years now. I can confidently say that this is one of the nicest, if not the nicest, places that we have ever stayed. The home was absolutely beautiful, with numerous comfortable seating areas where we could all gather and talk in a very relaxed way. The kitchen was well appointed. The view of the water was fantastic. Tammy is extremely responsive and helpful. Thank you for a wonderful stay!
Carrie N.
July 2026
Oh my gosh. We were so sad to leave. This house is absolutely perfect and the memories we made will last a lifetime. The kids were outside from sun up to sun down. We did yoga with Carol on the upper deck (this is a must) with the sound of birds and water. We kayaked, had a hibachi chef come, swam, relaxed on floats, and enjoyed the beautiful views. We can’t wait to go back. Tammy is so responsive and the best I’ve ever worked with. I’ll dream of that special house until we go back again!
Gail D W.
July 2026
Tammy was an exceptional host and helped us have a wonderful Fourth of July in an incredible location. She was remarkably responsive to our questions and helped us feel right at home. The property is beautiful and completely matched our expectations based on photos/descriptions in the listing. We were thrilled with our experience and definitely would consider staying stay at this property again. Will be recommending this property to friends in the region!
Micah B.
July 2026
We had such a great stay here. It was a quick trip, but this house made it feel like we packed a full vacation into just a few days.There was always something to do, from the game room with the arcade games and air hockey to the poker table and all the great spaces to hang out. We also loved the waterfront setting.One of the highlights of the weekend was hiring a private hibachi chef to cook dinner at the house. It turned into one of those evenings where everyone was laughing, eating, and just enjoying being together. It was such a fun experience and definitely one we'll remember.
Abby W.
July 2026
This was such an incredible stay! All questions were answered promptly and we were even given suggestions for local Restaurants etc. We hope to return again! Thank you!!
Wendy P.
June 2026
We had a fantastic time, and look forward to visiting again soon!
Milad N.
June 2026
This place exceeded our expectations! We were relaxed as soon as we walked through the front door. The space was clean, beautifully decorated, and the view was spectacular! The swim spa was a highlight, the lawn was big enough for games, and the beach next door to launch kayaks was incredibly convenient. So many options for rooms to hang out & the screened in porch was family favorite. We were happy with everything about the location, the house, and would 100% recommend staying here! Hosts were generous & helpful!
Kelly H.
June 2026
Gorgeous home! We had the most amazing stay. The house was absolute perfection and Tammy was easily available via text with any questions we had. We can't wait to go back!
Lori M.
June 2026
We had a wonderful time at Tammy's - comfortable well-stocked home with waterfront views. Enjoyed the several amenities as noted on the listing and barely left the house during our stay. Tammy was very responsive and proactive in reaching out, left clear instructions and a guidebook. No extensive list of tasks for check out. The place was clean and we had everything we needed. This is the perfect place for a relaxing vacation on the water, gathering with family to cook (and order some crabs), watch movies, play games and take it slow.
Mazen T.
June 2026
This home is beautiful inside & out. The views are amazing & the house is immaculately clean & offers so much from the game room & the kayaks. Whether it be a couples getaway to a whole group it’s an amazing experience. Lots of birds if you’re a nature lover. Thank you Tammy!!
Elizabeth
May 2026
This house was a wonderful place for a long weekend with the family. The kitchen was extremely well stocked and made it so comfortable to cook almost all of our meals in. The view of the water was beautiful and private. The game room and activities area was well stocked to help keep my 3 year old entertained all weekend. I highly recommend this property for families!
Maya S.
May 2026
My wife and I needed a break from the everyday hustle, and this place was exactly what we were looking for. If I could give it 10 stars, I absolutely would. The home was beautiful, comfortable, and set in an amazing location that made it easy to relax and unwind. The property offered so many activities to choose from, and the game room was a blast — even for adults! Tammy was incredibly responsive throughout our stay and provided great local recommendations that made the trip even better. We truly enjoyed our time here and would highly recommend this home to anyone looking for a peaceful and fun getaway.
Nate C.
May 2026
From the moment we walked in, everything exceeded expectations. The home was spotless, beautifully designed, and somehow even better than the photos. You can tell the host put real thought into every detail—from the comfortable furniture to the fully stocked kitchen and little touches that made it feel like home. The location was perfect—quiet, safe, and convenient to everything we needed. Whether it was relaxing in the living space, getting a great night’s sleep in an incredibly comfortable bed, or enjoying coffee in the morning, every part of the stay felt easy and stress-free. What really stood out was how seamless the entire experience was. Check-in was simple, communication was clear and responsive, and everything worked exactly as it should. No surprises—just a genuinely great place to stay. If you’re considering booking this home, don’t hesitate. This was one of those rare stays where everything just felt right. I would absolutely stay here again.
George E.
May 2026
The home was beautiful and immaculately clean
Erica D.
May 2026
This house exceeded expectations in every way. The place was clean, well organized, and exactly as described. The location is conveniently beautiful and quiet, making it easy to rest and enjoy the stay. The nice big hot tub and the comfortable back yard near the water were fantastic. The rooms are beautifully appointed, with a beautiful view of the water. Communication with the host was quick and helpful, and Tammy was very pleasant and welcoming throughout the day. All in all, a very high quality stay and a place that I would certainly highly recommend to others.
Shia Z.
April 2026
The place was immaculate and thoughtful. Tammy and hosts were so helpful, proactive with check in, and communicated quickly. One of the few and only times the place far exceeded the pictures. Would highly recommend.
Cecilia A.
April 2026
Our family had an amazing stay. The house was exactly as pictured and had everything we needed. Our son barely used his devices because he was too busy fishing and kayaking with his dad, and we spent our nights hanging out in the game room instead of watching TV. The outdoor spaces are incredible. While they were out on the water, I did a private yoga session recommended by the host, and then relaxed in the sauna and read on the dock. Dinner at Knoxie’s was great too. Such a perfect mix of relaxing and quality family time, we will definitely come back!
Hillary S.
April 2026