Private Pool & Stunning Bay Views on Kent Island

Stevensville, Maryland
$837 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 11

Max Sleeps

Night 2 nights

Min Stay

Experience the Difference: Professionally Managed by iTrip Annapolis

Kent Island Chesapeake Bay Cottage with Private Pool & Sunset Views



Welcome to your dreamy poolside getaway! This charming summer cottage offers a private pool and breathtaking views of the Chesapeake Bay. The oversized wrap-around deck is perfect for sipping morning coffee or enjoying stunning Bay sunsets. (Pool is open April through October.)



Sleeps up to 11 Guests

3 Bedrooms • 3 Bathrooms • Ideal for up to 8 adults + 2-3 children



Main Floor (Upstairs):

King Suite Bedroom: King bed + En Suite Full Bath

Twin Suite Bedroom: 2 Twin beds + En Suite Bath

Open Family Room: Queen Sleeper Sofa + Full-size Daybed



Lower Level:

Private Guest Room: Queen Bed + Full Hall Bath

Sleeping/Family Room: Full Bed + Twin Daybed



Highlights:

Private Backyard Pool (open April 23–October)

Wrap-Around Deck with Chesapeake Bay Views

Multiple Dining Areas:

Indoor Dining Table (seats 8)

Deck Dining Table (seats 6)

Poolside Table (seats 6)

Front Yard Table (seats 6)

Weber Propane Grill

High-Speed Internet & WiFi

3 Flatscreen TVs

3 Bicycles for guest use

NASA-developed AquaSpace Water Filter

Luxury Linens + Complimentary Toiletries Starter Kit

Full Washer & Dryer

Circular Driveway Parking for 4–5 Vehicles

Note: Home uses window A/C units (no central air)

Keyless Entry through garage door keypad



Location:

Downtown Annapolis – 19 miles (~25 mins)

U.S. Naval Academy – 19 miles

Washington, DC – 48 miles

Baltimore – 43 miles



House Rules:

Minimum Age: One guest must be at least 25 years old

No Smoking, No Pets, No Parties or Events

Respect the home as if it were your own – this is a cherished private residence.

Please be courteous to neighbors and observe quiet hours.

Check-in: 4:00 PM

Check-out: 11:00 AM

Experience the Difference: Professionally Managed by iTrip Annapolis

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1996 Sq Ft (185 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • POOL/SPA

    Private Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site
  • ENTERTAINMENT

    Games Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 11

Map Map

School District Rates & Availability

Review Review

  • Michael S.

    Submitted Aug 10, 2025

    Stayed Jul 20, 2025

    Great time at a nice place and location.

  • Grace M.

    Submitted Sep 3, 2024

    Stayed Aug 18, 2024

    We loved everything about the Kent Island House! Would book again in a hot minute

  • Caitlin T.

    Submitted Aug 27, 2024

    Stayed Aug 16, 2024

    We really enjoyed our stay here. The house is spacious and had everything we need. The pool was great, and the garage is full of fun floaties and pool toys. The house has a perfect location with a fun restaurant and beach nearby.

  • Taylor W.

    Submitted Aug 7, 2024

    Stayed Jul 26, 2024

    Was the perfect spot for a nice weekend getaway with some friends.

  • Taliesin D.

    Submitted Sep 5, 2023

    Stayed Sep 2, 2023

    Everyone really loved the house and the location. The pool was great

  • James

    Submitted Aug 10, 2023

    Stayed Dec 31, 1969

    Nice home with large deck. Pool is great to beat the heat. The house has room enough for 3 couples to have their own private room and full bath.

  • Paula S.

    Submitted Aug 3, 2023

    Stayed Jul 22, 2023

    The highlight by far is the pool - it totally made our stay. There are jellyfish in the bay as the water heats up, so this was a huge advantage for our group. As a plus, the house has a bunch of fun pool and lawn toys. We had a blast in the pool and on the lawn, which is very spacious. The house itself comfortably sleeps many people. It was very clean and well-stocked with plenty of towels and linens, dishes and cooking utensils, etc. However, the house was 94 degrees when we arrived, presumably because the AC hadn't been turned on early enough ahead of our arrival. One of the ACs ceased to work on two days of our trip (kept running, but didn't blow cold air). We fiddled with it a bit; eventually turning it off for a while until it did work but the main floor of the house heated up very quickly in the meantime. Only one door (and no windows) has a screen and that screen is broken, so we really relied on that AC. There are ACs in all of the main rooms/sleeping areas, but for a house of that size that is presumably a real draw for summertime use, central air would be a major plus. The open spiral staircase may pose access issues for some travelers and/or could be dangerous for small children. We had some issues with trash pick-up, communicated with the manager several times and it was finally resolved but we had very full bins all week. I understand that trash pick-up can be challenging on the island...understandably. Overall we would rent this place again.

  • Wayne N.

    Submitted Jun 29, 2023

    Stayed Jun 21, 2023

    Great place and location

  • Adolfo P.

    Submitted Sep 14, 2022

    Stayed Sep 9, 2022

    The house was in a great spot being next to Kentmorr Restaurant and Dirty Dave's Tiki bar. We went boating one day so the Marina right next to us was also helpful. There was plenty of parking and the desk space was used a lot. The pool ended up being disappointing as it looked green(even tho we were told it was treated) and not safe to swim in the entire weekend. A snake ended up there one day as well. The upstairs guest bedroom only had a bunk bed when the vrbo page lists 2, so that should be corrected. Overall a fun weekend had by all, but we reserved this house to use the pool and being unable to use it was a bummer.

  • Jackie F.

    Submitted Sep 11, 2022

    Stayed Sep 1, 2022

    I cannot emphasize enough how perfect this house is for a group of friends or family, looking for a quick getaway, with every amenity you could wish for! The house itself was a fantastic size, and very well stocked with linens, beds, and hangout space - all of which is crucial for a large group. The pool was an incredible bonus - well maintained and a blast for our weekend. This house is also actual steps away from the wonderful Kentmoor Restaurant and Tiki bar, which was such fun icing on the cake! Our group loved this house and is already scheming for our next getaway!

Your dates are Available!

Total

Includes taxes and fees
$837+
View details