Entire home

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

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. - Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly (Stevensville)
A rustic building with a sign reading "Rustico Restaurant & Wine Bar" and a large outdoor fountain surrounded by vibrant flowers. - Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly (Stevensville)
A living room with a view of the water, a tufted sofa, and a small table with a lamp. - Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly (Stevensville)
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. - Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly (Stevensville)
A living room with a sofa, ottoman, and coffee table, a ceiling fan, and a large window with blinds. - Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly (Stevensville)
Consider a stay at Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly and take advantage of a firepit, a garden and laundry facilities. Guests can connect to in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Add dates for prices

About this property

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

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Smoke-free property

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

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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 allowed

Service animals are welcome, and 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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Located in Stevensville, this holiday home is on the waterfront. Hammond-Harwood House and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and some of the area's activities can be experienced at Queenstown Harbor Golf and Bay Hills Golf Club. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with cycling. Visit our Stevensville travel guide
View more Holiday homes in Stevensville
Map
Stevensville, MD

What's nearby

  • A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.
    Sandy Point State Park
    15 min drive - 8.7 miles
  • Matapeake State Park
    4 min drive - 2.2 miles
  • Paul Reed Smith Guitars
    6 min drive - 3.7 miles
  • Island Dog Park
    6 min drive - 3.9 miles
  • Love Point State Park
    9 min drive - 7.1 miles

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

Frequently asked questions

Is Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

Where is Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly located?

Situated on the waterfront, this holiday home is steps away from 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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Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 27 out of 29 reviews
Rating 8 - Good. 1 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 1 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10

Cleanliness

10

Location

Reviews

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
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
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

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

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 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
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

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

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
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
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

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
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