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Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Stevensville vacation home with kitchen

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Photo gallery for Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

A spacious room with a large sliding glass door leading to a deck with outdoor furniture and a view of the water.
A living room with a view of the water, a tufted sofa, and a small table with a lamp.
A modern kitchen with white cabinets, a stainless steel microwave, and a built-in oven. There is a dining area with a white table and blue patterned bowls.
A rustic building with a sign reading "Rustico Restaurant & Wine Bar" and a large outdoor fountain surrounded by vibrant flowers.
A living room with a sofa, ottoman, and coffee table, a ceiling fan, and a large window with blinds.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Stevensville, MD
  • Place, Northern Chesapeake Bay
    ‪1 min walk‬
  • Place, U.S. Naval Academy
    ‪29 min drive‬
  • Place, Annapolis City Dock
    ‪32 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪60 min drive‬

Room options

About the area

Stevensville

On waterfront.Within a 5-minute walk of this Stevensville vacation home, you'll find Chesapeake Bay and Northern Chesapeake Bay. Matapeake State Park and Paul Reed Smith Guitars are also within 3 miles (5 km).
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What's nearby

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • Chesapeake Bay Bridge - 16 min drive - 14.6 km
  • U.S. Naval Academy - 29 min drive - 28.0 km
  • Annapolis City Dock - 32 min drive - 29.8 km
  • Arundel Mills Mall - 59 min drive - 67.7 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 31 min drive

Restaurants

  • ‪Chick-fil-A - ‬8 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Starbucks - ‬9 min drive
  • ‪Hardee's - ‬8 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly

Summary:
Escape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 hours from Washington D.C. and Baltimore. With stunning water views, a private dock, and a fully fenced yard, this home is the perfect setting for family vacations, couples’ getaways, and small group adventures.

The Space:
Start your mornings with coffee on the deck over the bay. Spend your days fishing or crabbing from the dock, exploring Kent Island’s scenic trails, or visiting Annapolis’ charming shops and historic sites. In the evenings, unwind with a glass of wine as boats drift past your backyard.
Inside, you’ll find a welcoming open floor plan, comfortable furnishings, and three cozy bedrooms designed for restful nights. The home is stocked with modern conveniences including Wi-Fi, smart TV, and a well-appointed kitchen.

Why Guests Love It:
- Stunning bay views from the deck & living room
- Private dock for fishing, crabbing, or launching kayaks
- Fully fenced yard — perfect for pets and outdoor games
- Quick drive to historic Annapolis, local dining, and waterfront activities
- Easy access from Washington D.C. & Baltimore for weekend getaways

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.

Guest Access:
Key Coded entryThis property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
The property is in a lovely neighborhood, we ask guests to be courteous to our neighbors and the neighborhoods.

Other Things to Note:
Pet-friendly with a $200 fee per dog (max 2). Starter supply of toilet paper and paper towels provided; please bring extras for longer stays

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Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • Games
  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Boat
  • Foosball table
  • Optional golf privileges
  • Cycling nearby
  • Fishing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

An additional lease agreement is signed for the property once booked and if guests are bringing their furry friend there will be $150 pet fee.

Pets

  • Pets are welcome
  • Service animals are exempt from fees
  • Note from host: Charge may apply

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property is also known as

664b6577e847210056347f17

Frequently asked questions

How close is Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly to the airport?

This vacation home is 26.7 mi (31-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly to the beach?

This vacation home is 8.8 mi (14-min drive) from Sandy Point Beach.

Does Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly?

No, there is no casino at this vacation home.

What time is check-in at Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly?

Check-in begins at 4:00 PM.

Is there free parking at Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly?

Free parking is not available at this vacation home.

Does Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly have a pool?

This vacation home does not have a pool.

Does Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly have a spa?

There are no spa services available at this vacation home.

How close is Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly to downtown Stevensville?

This vacation home is 2 mi away from Stevensville.

Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 30 out of 32 reviews
Rating 8 - Good. 1 out of 32 reviews
Rating 6 - Okay. 0 out of 32 reviews
Rating 4 - Poor. 1 out of 32 reviews
Rating 2 - Terrible. 0 out of 32 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Place was beautiful and it was so nice to be able to bring my dog who loved the place just as much as we did!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location, very well maintained and appointed.
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Stay

Beautiful location and wonderful hosts.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This bayfront property was beautiful both inside and outside. The house was perfect in size, decor, function and comfort for our family including our dog, who got to spend every day outside in the fenced-in yard, getting her own bay-view. We spent hours outdoors, day and night, and the fire pit became a special nightly ritual to watch the sunset. The owner/management company were very responsive. I would highly recommend this property!
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at a great location

House was as advertised with all the comforts needed for our stay. Convenient location to Annapolis and other local spots.
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning views, great location, quiet and friendly neighborhood, beautiful sunsets on the bay. This house is spacious with an open floor plan - lots of natural light, very clean, and comfortable beds. We had our dog with us so the fenced yard was a bonus. Kitchen was well stocked for cooking, full sets of dishes and plenty of silverware and coffee mugs. Soft linens and snuggly blankets made it feel like home. Jennifer was great to work with from booking throughout our entire stay. We would stay here again!
Stayed 6 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was lovely and the view beautiful.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location and view cannot be topped. You can sit for hours watching the bay. We enjoyed the fire pit, dock, and just everything about the backyard. The home is beautifully decorated. Totally pleasant experience. Can't wait to return. Was also great to be able to bring our four legged friend along. Location is close to everything you need or want.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely time staying here - house and neighborhood are adorable and great for a quiet relaxing weekend! Our pup loved the fenced in yard.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, well-appointed, and organized for relaxation. View could not be better. Good setup for dog with fenced area. We enjoyed our stay!
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bay View

The views from the back yard were exceptional, the house was clean ant the master bed was amazingly comfortable.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional Views

Beautiful and tranquil stay with outstanding views to relax. Would repeat again.
Stayed 6 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Property on Kent Island!

This house has EVERYTHING but the VIEWS are the absolute best! The decor is inviting, the kitchen fully stocked with anything you need, outside has plenty of seating with a beautiful dock and fire pit. Bedrooms are spacious, "viewing room" was a favorite, we loved everything about this rental!
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

Beautiful home and perfect views! It was very clean and comfortable. More spacious than it looks in the photos. Jennifer was very responsive and friendly. Would definitely come back to stay here!
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house and view!

Loved everything about this house! The view, the furnishings and the quiet neighborhood were all amazing. The weather was bad (cold, rain, snow) but it did not stop us from having a great time!
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay and will be sure to come back. it was our first time in Maryland to attend a wedding. our dog left the backyard as well as walks around the neighborhood.. my wife said she could sit in the backyard all day. Thank you Jennifer for hosting us and we hope to return soon.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had such a great vacation at this property! The neighborhood was perfect for long dog walks -- quiet, safe and full of charm. Several parks within the neighborhood. The house itself is beautifully decorated and felt instantly welcoming. The kitchen was thoughtfully stocked with everything we needed to cook meals at home, which we really appreciated. Our dogs absolutely loved the spacious fenced yard -- it gave us peace of mind and them plenty of room to play. The views of the Bay were stunning, especially at sunset. We'd definitely stay here again!
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quick Getaway on the Bay

We were looking for a quick trip to get away from our normal routine and found this absolute gem of a place on the water. The house itself was in a prime location. A short drive to Annapolis and local food. The house was very clean and had such a great view. The upstairs loft kept our kids busy with the arcade, foosball and books. The backyard was very inviting and we spent as much time as we could back there. Drinking a morning coffee looking out to the water was very relaxing. This was a 10/10 stay for us and will definitely look to return when the weather warms up!
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday weekend

My son and I flew out to Maryland to celebrate my daughter's 21st birthday while she was at UMD. The location was perfect and ideal for traveling between Kent Island/St. Michaels and Annapolis/Baltimore, and was less than an hour from College Park for my daughter to drive and meet us. The house is charming, comfortable and clean. The neighborhood is quiet and the view was wonderful. We really enjoyed our stay and it made for a perfect birthday weekend.On a side note, the property mgmt company was wonderful and very responsive. Only days before our trip there was a water pressure problem and I was informed that the work would likely not be in time for our trip. They offered other accommodations on St. Michaels in a more expensive property at no charge as well as any other assistance I might need. In the end, the water problem at the original property was fixed and we had a lovely time. Thank you for everything.
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A large and beautiful place to stay with amazing views on the water. The fact that we could bring our furry friend made it even more enjoyable. The beds were comfortable and the house was clean with super easy check-in/check-out. The owners thought of everything with regards to this rental and they reached out to see if we needed anything but it was perfect. Would definitely come back in the future.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was beautiful inside and out! The living room was very spacious and our kids absolutely loved the play area and toys upstairs. The best part, however, was the backyard - sunset views and lots of space to run around.
Stayed 3 nights in May 2026
Verified review

4/10 Poor

Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Sep 2025

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