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Escape the city hustle to relax on the Chesapeake! Savor our three-bedroom Cottage in this peaceful western shore spot where only our invited guests will find you. Stroll 66 feet to the water or cozy up indoors by the fire to watch the sunset. Explore two acres of green space; enjoy our pier and 45 amenities; or ask about hosting events. Stay in, or venture to nearby historic Annapolis or local waterfront dining, grocery stores, take country drives, go antiquing. Then come on back to fully relax, bond, recharge. The Space: Top Ten reasons to choose our Cottage as your next place to retreat to: 1. Best kept secret on the Chesapeake, with far more open space and country-like waterfront than the crowded neighborhoods in this area. We are less than 45 minutes from many parts of Washington DC, Baltimore and Alexandria. 2. The western shore is easy to access. You won't have to fight the Chesapeake Bay Bridge traffic getting to the east side of the bay. FREE PARKING ON SIGHT. 3. Explore Local > Less than three minute drive to Deale, MD where you can get groceries, eat, fish, sail, do water sports and more local activities. 4. Kayaking, fishing, floating/swimming, or catching crabs right off our private pier are all included in summer, and enjoy movies, football, indoor games, gorgeous views, and long conversations by the fire in winter. Access to two acres of private green space includes my private pier, just 150 feet away from The Cottage. We provide lawn and indoor games, indoor and outdoor cooking, swings, fire-pit, outdoor shower, other fun amenities. 5. The Cottage has hosted many private corporate or spiritual retreats, family reunions, group BBQ/crab feasts, and weddings. (Arrangements and charges for events made separately from your booking.) BBQ grill and pots for cooking crabs are provided. Extra sleeping accommodations are also possible for larger groups staying at the Cottage in our Carriage House Retreat, which is attached to the Cottage garage. 6. If The Cottage is booked, we have a close sister property called the Flat Plus which is next door to the Cottage. If you're a big party, I sometimes even rent out my own home, "Chesapeake Paradise House," and even our adorable Camper or Carriage House for "glamping." Some of the amenities are share, but don’t worry--you won’t trip over other guests, if there happen to be any, on our two-acre property, because you have exclusive, private access to your three bedrooms and two-bath Cottage with its own shady lawn, waterfront lounging, dining indoors or outdoors, firepit, and swings. 7. The Cottage is your home base for your getaway or retreat in a country-like little neighborhood near the end of a point of land with water on both sides. Nobody will find you here unless you give them the address, which will be provided to you upon registration. 8. Daytime excitement & nighttime wonder. Start your days with amazing sunrises. During the day, enjoy birdsong, waterfowl, and blinding sparkles near the water or sitting in the shade under our tree. With no city streetlights, the star gazing and our unique “firefly trees” always surprise and delight folks who don’t expect that so close to the city. 9. Chesapeake Paradise (what we call this sweet sacred spot) was named by Travel + Leisure Magazine as the “most wished for” Bnb in Maryland! Spend time alone while you’re here or feel supported by me and my lovely local property manager, Alice. I have been sharing my lovely place next door for over 11 years, and always have the greatest guests, who have been thrilled and are so much fun to host (see reviews below). My team and I are here to support you as much or as little as you need while staying in the Cottage. 10. Bottom line, Chesapeake Paradise is the most versatile and consistently enjoyed space in this local area; its country-like open spaces are a far cry from the usual crowded waterfront neighborhoods and tiny lots often found on the western shore. Couples will find the tranquility you seek, and the close-up nature and unique decor will make your special getaway more memorable. Families will smile all day long because there is enough room in the cottage for everyone to have their own personal space to rest and relax; with many natural adventures, movies, and games/toys to keep kids busy and fascinated. Corporate meeting organizers love the space to be able to accommodate productive focused projects and board retreats, while treating folks to beautiful views and the feel of really "getting away," even though its so close to DC. Dogs: Your furry loved ones are welcome to the Cottage. Each dog staying with you will add an additional $18 per night to the rental fee. If you have a puppy or kitty, there is a $250 refundable deposit in the event that your pet has an unfortunate accident or accidentally damages the Cottage. Please pay the deposit by check or cash when you arrive, separate from the booking software. We provide helpful amenities for all seasons like throw blankets for movie nights, extra towels, big floaty things for playing off the pier in summer, and other small touches that can make all the difference in creating your happy, memorable experience. Please feel free to contact us by putting in any date you see open (click on the tab above the large photo to see our calendar). Just grab a range of dates if you want a shorter get-away, and write to express your interest in planning a longer stay, need a short-term rental, or want to host an event! We are happy to answer any questions you may have, as we love sharing this amazing spot with our guests! Guest Access: You'll have your own space with a waterfront connected to the front lawn. You and your party have access to my private pier, as do other guests who may come and go. BBQ is located in the "common area" in Cottage, and we provide you with outdoor table and chairs, lounge chairs, a large cast-iron firepit, two single kayaks, one single open-ocean kayak, and one two-seater open-ocean kayak, as well as a canoe and big floaty things for playing or lounging on the water during times when its good to swim! You'll have two acres to play on or explore, nearby walks on a wooded lane or by the Chesapeake Bay, a lovely country-like setting with plenty of waterfront dining, amenities, and sights nearby. Even though there are four properties at Chesapeake Paradise, you'll have plenty of privacy and space--it feels much less crowded than lots of neighboring waterfront properties. I love sharing this gorgeous spot, and my property manager, Alice, and I interact with guests based on their needs. Let me know upon booking what level of support you would like so that we can accommodate you effectively. I respect your need for privacy, but we are also happy to provide you history of the area, support with your onsite activities, or local recommendations to check out, Commissioning Week and other stays booked well in advance may be subject to different price structure.
(18 Reviews )
Keith D.
April 2025 5.00We were the first ones to use the Cottage following the kitchen remodel. The new open floor plan is very attractive with beautiful views of the creak and Chesapeake Bay throughout most of the house. My wife is a chef so we cook most of our meals and the new kitchen was quite workable for all dishes great and small. Shawn was attentive as needed and even furnished us with pictures of the culinary equipment there, so we knew exactly what to bring. The area is quaint and quiet but there are lots of quality restaurants nearby, and Annapolis is a only short drive away. The Cottage feels like the perfect place to stay and write the great American novel or compose a symphony.
Biplab P.
March 2025 5.00Nestled in the tranquil riverside landscape of southern Maryland, just beside the southern Chesapeake Bay, this home is a hidden gem—truly extraordinary in every sense. If you're seeking a brief escape from the bustling energy of Washington D.C. or Baltimore, this haven offers the perfect retreat. We were two families with four children—two young adults heading to college and two spirited middle schoolers—and every one of us, regardless of age, found joy and peace here. From the breathtaking natural surroundings to the simple pleasure of kayaking through calm waters, each moment felt like a gentle reset for the soul. What truly elevated the experience was our host, Shawn. More than just a “super host,” she embodied hospitality in its finest form. Her attention to detail, her care for comfort, and the thoughtful touches throughout the home surpassed even the details of a Hollywood studio setting !
Vivian F.
February 2025 5.00Beautiful home with a lovely view. The house is very cozy and comfortable, great for entertaining and close to all of the amenities. The scenery is spectacular and relaxing. I could not ask for a more attentive host. Shawn was very friendly and went above and beyond to make our stay very enjoyable. We will definitely be returning.
David B.
September 2024 5.00Shawn was a fantastic host! very knowledgeable about the area and extremely accommodating. The cottage was quirky but beautiful, and the perfect location right on the water. couldn't have asked for a better family vacation spot!
Erin C.
August 2024 5.00Was just the quiet, relaxing break we needed. Host was very helpful and friendly and we felt right at home. House was well stocked and comfortable. Excellent outdoor space on the water for that early cup of coffee , some kayaking, or s’mores around the fire pit.
Ann M.
August 2024 5.00Last minute trip for relaxation. Perfect spot and we got to bring our dogs. Loved kayaking and just sitting by the water. Thank you for sharing your beautiful property
John O.
August 2024 5.00She has everything you could imagine needing. It was beautiful, quiet, restful.
I would come back and stay in the main space or bring a large group. Shawn makes this experience amazing and went above and beyond for me and my girls. The cottage was as advertised. It’s simple, quiet, and exactly what we needed… nothing we didn’t.
Chesapeake Paradise is a hidden gem with more open space and tranquility than other crowded neighborhoods. We're conveniently located less than 45 minutes from Washington DC, Baltimore, and Alexandria.
Our western shore location allows you to avoid the Chesapeake Bay Bridge traffic, and we offer free parking on-site for all our guests.
Only a short drive to Deale, MD for groceries, dining, fishing, and water activities. Nearby sailing destinations and the historic Annapolis are also just a scenic drive away.
Whether it’s kayaking, fishing, or swimming in summer, or cozying up by the fire with indoor games and movies in winter, there’s always something to enjoy at Chesapeake Paradise.
The Chesapeake Paradise House is next door to the Cottage, offering additional space for larger groups. We also have a charming Camper and Carriage House for a unique “glamping” experience.
Named by Travel + Leisure as the “most wished for” BnB in Maryland, Chesapeake Paradise offers an unforgettable retreat experience with both daytime excitement and peaceful nights under the stars.