Cottage in Anne Arundel County, MD
8 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this cottage rental
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.
NOTE: BASIC nightly rate is for 4 occupants--`GRANDE` means $30 extra per night for each additional occupant above the basic limit, and max 8 guests allowed.
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.
WELCOME!! Important Rule: Relax, Have FUN, and be sure to Let me Know if You need Absolutely Anything!
SUNSCREEN and LINENS:
I know it seems weird--and I`m really NOT super picky--but we have had to replace many white sheets and towels because they turn orange from people using them with sunscreen on! Please shower first, esp. if you have light sheets, and use regular pillows for your head, not the decorative ones with pillow shams. Thanks! Also, the seats on our couch don`t zip off for washing, so we really appreciate minimal food or spills on them as a good dose of red wine would mean replacing the couch. Thanks so much, again.
No red wine or stain-creating food around leather or upholstered furniture.
ABOUT SWIMMING AND BOATING
I love to swim off the pier and have done so with a passion for many years! Many guests enjoy swimming here or floating on the inflatable raft. We provide big, fun floaty things since the bottom is muddy. I swim off the pier many months of the year; however, there are some important caveats, and ALL WATER and BOATING ACTIVITIES are undertaken at your own risk. Please read the following if you are considering going in the water:
Please bring your own safety flotation devices (life jackets) for children of all ages or adults who are non-swimmers. We do provide life jackets in various sizes and thickness as the Coast Guard requires that they be with you while in watercrafts; however we cannot guarantee them, especially for children or people who cannot swim. We love that our guests seem to be very careful and use lots of common sense. YAY!
No children under 12 on the pier without life jacket or very close supervision of an adult. (Children in the yard at any time must also have adult supervision.)
The ladder can be slippery and barnacles can sometimes build up and be sharp, so you may need water shoes. You can expect the bottom to be deep `silky mud` (I like it!).
DO NOT GO IN THE WATER WITH A FRESH CUT OR SKIN LACERATION due to bacteria that is sometimes found in the Bay.
NO DIVING OFF PIER OR JUMPING OFF SIDES OF PIER!!!! Experienced swimmers may jump off the end with great care if you FIRST TEST WATER DEPTH as it can change with the tides and become very shallow (plus bottom is very muddy and could have glass in it so wear water shoes if you put your feet down).
Occasionally there are sea nettles here (mildly stinging jellyfish that show up for a few days or even a few weeks (RARE) in late summer, usually for a day or two in July or August; but they’re definitely gone by mid to late September.
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.
NOTE: BASIC nightly rate is for 4 occupants--`GRANDE` means $30 extra per night for each additional occupant above the basic limit, and max 8 guests allowed.
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.
WELCOME!! Important Rule: Relax, Have FUN, and be sure to Let me Know if You need Absolutely Anything!
SUNSCREEN and LINENS:
I know it seems weird--and I`m really NOT super picky--but we have had to replace many white sheets and towels because they turn orange from people using them with sunscreen on! Please shower first, esp. if you have light sheets, and use regular pillows for your head, not the decorative ones with pillow shams. Thanks! Also, the seats on our couch don`t zip off for washing, so we really appreciate minimal food or spills on them as a good dose of red wine would mean replacing the couch. Thanks so much, again.
No red wine or stain-creating food around leather or upholstered furniture.
ABOUT SWIMMING AND BOATING
I love to swim off the pier and have done so with a passion for many years! Many guests enjoy swimming here or floating on the inflatable raft. We provide big, fun floaty things since the bottom is muddy. I swim off the pier many months of the year; however, there are some important caveats, and ALL WATER and BOATING ACTIVITIES are undertaken at your own risk. Please read the following if you are considering going in the water:
Please bring your own safety flotation devices (life jackets) for children of all ages or adults who are non-swimmers. We do provide life jackets in various sizes and thickness as the Coast Guard requires that they be with you while in watercrafts; however we cannot guarantee them, especially for children or people who cannot swim. We love that our guests seem to be very careful and use lots of common sense. YAY!
No children under 12 on the pier without life jacket or very close supervision of an adult. (Children in the yard at any time must also have adult supervision.)
The ladder can be slippery and barnacles can sometimes build up and be sharp, so you may need water shoes. You can expect the bottom to be deep `silky mud` (I like it!).
DO NOT GO IN THE WATER WITH A FRESH CUT OR SKIN LACERATION due to bacteria that is sometimes found in the Bay.
NO DIVING OFF PIER OR JUMPING OFF SIDES OF PIER!!!! Experienced swimmers may jump off the end with great care if you FIRST TEST WATER DEPTH as it can change with the tides and become very shallow (plus bottom is very muddy and could have glass in it so wear water shoes if you put your feet down).
Occasionally there are sea nettles here (mildly stinging jellyfish that show up for a few days or even a few weeks (RARE) in late summer, usually for a day or two in July or August; but they’re definitely gone by mid to late September.
Amenities at Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Non-smoking
Pets allowed
Family friendly
Map of Anne Arundel County, MD
Ratings and reviews
10 / 10Outstanding·Aug 2025
We had an outstanding stay at Chesapeake Paradise and are happy to add our glowing accolades to all the justly deserved positive reviews for this property. Although Shawn was out of town at the beginning of our stay, her communication was top-notch. She checked in with us frequently to assure all was well. We knew if we needed assistance in any way it was a text away. The house was immaculate and every comfort and convenience was provided. We woke to a stunning view of the water from our comfy beds, could prepare meals effortlessly in a well-stocked kitchen and enjoyed oodles of room to spread out in the thoughtfully designed cottage. Maps, brochures, a binder of information and the website provided guidance to restaurants, local activities and all we needed to plan our week. The outdoor space was the highlight of our time. As described, we had direct access to the water. We swam, canoed, kayaked and floated. We were lucky enough to share the week with a multi-generational family in the adjacent building on the property. We enjoyed common fire pit time, talks on the pier, and having our dogs play together. There were so many “extra” perks, like the multiple types of swings, lounge chairs, tables, grills, and games. When Shawn returned to the property, we enjoyed wonderful conversations. She was available as much as we desired or needed, yet was not intrusive on our privacy. We would rent here again without hesitation.
10 / 10Outstanding·Sep 2024
Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more.
10 / 10Outstanding·Aug 2024
Amazing property and location. Views are amazing. Home has EVERYTHING You need for a great vacation. Very well equipped. Have rented many VRBO and no one has covered the necessities like Shawn. If you want to relax and also be active this is a perfect home. We will certainly return 😊
10 / 10Outstanding·Jul 2024
Best sleep ever! Bed and pillows super comfy. Beautiful view. Stores and restaurants within minutes. Shawn is extremely caring.
$$$$
Top rated by guests
9.8Outstanding
(86 Ratings)
"We had an outstanding stay at Chesapeake Paradise and are happy to add our glowing accolades to all the justly deserved positive reviews for this property. Although Shawn was out of town at the beginn..."
Suzanne K.Don't miss out! Price and availability may change
