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Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill

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Your own private pool awaits you at this Summer Cottage
The home has views of the Bay from the wrap-around front porch.
The great room on the Main Floor/Upper level has views of the Bay.
The lower level open living/sleeping space is perfect for extended family and kids.
Stunning views of the Bay and Sunsets from the 2nd floor wrap-around porch.

Reviews

9.2 out of 10
Wonderful
3 bedrooms3 bathroomsSleeps 111996 sq ft

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Outdoor grill

Explore the area

View in a map
Stevensville, MD
  • Place, Matapeake State Park
    ‪5 min drive‬
  • Place, Romancoke Wharf County Park
    ‪6 min drive‬
  • Place, Paul Reed Smith Guitars
    ‪11 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪55 min drive‬

Rooms & beds

3 bedrooms (sleeps 11)

1st Floor

1 Queen Bed

Lower Level Family Room

1 Double Bed and 1 Twin Bed

Upstairs Great Room

1 Twin Bed and 1 Queen Sofa Bed

Upstairs King Suite

1 King Bed

Upstairs Twin Suite

2 Twin Beds

3 bathrooms

Lower Level Full Bath

Toilet · Shower only

Upstairs En Suite

Bathtub or shower · Toilet

Upstairs En Suite 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms
Garden

About this property

Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill

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
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
default

Pets

No pets allowed
default

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

About the neighborhood

Stevensville

Stevensville is home to this vacation home. Paul Reed Smith Guitars and Helen Avalynne Tawes Garden are local attractions and those in the mood for shopping can visit Queenstown Premium Outlets and Westfield Annapolis Mall. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium.
View more Vacation Homes in StevensvilleOpens in a new window
Map
Stevensville, MD

What's nearby

  • Matapeake State Park - 5 min drive - 5.8 km
  • Romancoke Wharf County Park - 6 min drive - 6.5 km
  • Paul Reed Smith Guitars - 11 min drive - 12.3 km
  • Island Dog Park - 12 min drive - 12.0 km
  • Love Point State Park - 15 min drive - 17.7 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 35 min drive

Restaurants

  • ‪McDonald's - ‬11 min drive
  • ‪McDonald's - ‬14 min drive
  • ‪Cracker Barrel - ‬11 min drive
  • ‪Dunkin' - ‬13 min drive
  • ‪Chipotle Mexican Grill - ‬11 min drive

Frequently asked questions

Is Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill?

As of Apr 16, 2026, prices found for a 1-night stay for 2 adults at Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill on May 15, 2026 start from $742, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill?

Check-in begins at 4:00 PM.

What time is check-out at Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill?

Check-out is at 11:00 AM.

Where is Bay Views, Private Pool & Steps from The Kentmorr Beach Bar and Grill located?

Situated in Stevensville, this vacation home is steps from Chesapeake Bay and Northern Chesapeake Bay. Matapeake State Park and Romancoke Wharf County Park are also within 6 mi (10 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 28 reviews
Rating 8 - Good. 6 out of 28 reviews
Rating 6 - Okay. 1 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 1 out of 28 reviews

9.2/10

Cleanliness

9.6/10

Check-in

10/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Michael S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great time at a nice place and location.
Stayed 4 nights in Jul 2025
Verified

8/10 Good

Taylor W.

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

Great stay

Was the perfect spot for a nice weekend getaway with some friends.
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Wayne N.

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

Great place and locatio

Great place and location
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Luz J.

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

Great place!!

Great experience!!
Stayed 4 nights in Jun 2021
Verified

10/10 Excellent

Jenna F.

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

Great location and property!

Enjoyable stay by all! Pool was fantastic and the location can’t be beat! Great communication with property manager!
Stayed 4 nights in Jul 2021
Verified

10/10 Excellent

Grace M.

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

Such a fun house!

We loved everything about the Kent Island House! Would book again in a hot minute
Stayed 5 nights in Aug 2024
Verified

10/10 Excellent

Caitlin T.

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

Great house and location

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.
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Taliesin D.

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

Wonderfull Time

Everyone really loved the house and the location. The pool was great
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Tracey P.

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

Great House

Wonderful house, great pool, nice quiet location with a great restaurant within walking distance. Will rent again!
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Patricia Y.

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

Perfect getaway for friends!

This place was PERFECT for a big group of friends to catch up by the water with beautiful views!! It was extremely spacious, clean and the location was great. Communication with the host was easy, and the checkin process was seamless. Highly recommend - I would rent here again!
Stayed 2 nights in Oct 2021
Verified

10/10 Excellent

Scott S.

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

Definitely want to come back!

We loved our stay at this property! The house is a fun cottage with 2nd story views of the Chesapeake and walking distance to a super fun tiki bar. Such a quick drive from NoVA - wish we'd realized this place existed years ago. We'll be making a trip back!
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Gary S.

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

Great place - exactly as advertised

We had a friend's weekend here, and we really enjoyed the property. Everything was as advertised. The sleeping accommodations are a bit tight for the number the house advertises it sleeps, but it's definitely as advertised. I would stay here again.
Stayed 3 nights in Jul 2022
From a partner site

10/10 Excellent

James

Pool with Tiki across the street

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.
Verified

10/10 Excellent

Kathleen O.

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

Great house!

This house was a great place for a larger group of women. The backyard was incredible; we spent the whole weekend there. There were definitely some things that could have been a little cleaner/updated, but everything was exactly as expected based on the posting. We'd gladly stay here again.
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Jackie F.

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

Perfect space in a perfect location

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!
Stayed 4 nights in Sep 2022
Verified

8/10 Good

Edward R.

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

Nice location..house needs some work.

The wrap around deck is rotting....air conditioners are loud but effective...spiral staircase is broken and dangerous. Overall...we had a good time. The house has everything you need.
Stayed 5 nights in Aug 2022
Verified

8/10 Good

HARRY M.

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

kitchen

house was perfect for our short get away with our family. nice size yard to play in, beautiful views of the bay (the grandkids loved watching the ships in the bay) very close to activities for hiking/biking and the pool was fantastic. the only down side was what was supplied in the kitchen. very limited pot/pan for cooking, bowls for mixing....
Stayed 4 nights in Jul 2022
Verified

8/10 Good

Adolfo P.

Liked: Cleanliness, check-in, communication, location

Nice house with great location.

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.
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

James B.

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

Great Stay on Kent Island!

Truly just picked this location on a whim on kind of short notice looking for something to do fairly close (from Western NY) this Summer but turned out to be a great house in a great part of Maryland. Everything you need at house, great pool, deck with view, etc. Kentmorr Tiki Bar/beach a short walk away is terrific but also Matapeake and Terrapin Parks with amazing beaches are a super short drive. And Sandy Point State Park is like a 20 minute drive away for the big, more typical beach experience. Would certainly come back and recommend Kent Island to any family looking for a fun new, beachy experience. PS - Big thanks to Sean for having so many tools etc on the ready at the house as well as I had to deal with waking up to a flat tire on my wife's Suburban on the 2nd morning. And of course everything went wrong with that simple job but luckily had tools to help get it done.
Stayed 4 nights in Aug 2021
Verified

8/10 Good

Layna J.

Liked: Check-in, communication, location, listing accuracy

Girls weekend 8/11-8/14

Lovely house with great views and lots of space! As another reviewer mentioned, this house is exactly as listed/pictured. 3 Bedrooms (with doors) and a large open room with a variety of (1) bed, futons, and couches. The pool was perfect and the house provided lots of floats for us to enjoy. The kitchen came fully stocked with spices, pans, serving trays, etc. The extra refrigerator in the garage was a huge bonus for our extra food/beverages. One important tip: the spiral staircase that connects the upstairs with the downstair! This was no issue for us, but is important to note for older family members or families interested in this property. We did have a leak in the Master bath on our 2nd day that was handled in a timely and professional manner. Shout out to Cathy from iTrip Vacations for the quick response and communication. Overall, I would recommend this house to any group looking for fun in the sun and not a luxury getaway.
Stayed 3 nights in Aug 2022
Verified

10/10 Excellent

Paula S.

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

Kent Island House with Pool and Bay Views

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.
Stayed 7 nights in Jul 2023
Verified

8/10 Good

Mildred N.

Liked: Check-in, communication, location, listing accuracy

10/1 through 10/3

We enjoyed the deck and the view tremendously; however the property is very outdated and needs a few repairs (decking) to be safe. There were melted popsicles left in the frig (not ours but found them upon our arrival. There was no dish soap (we bought some and left it there for other renters) and no dishwasher soad.
Stayed 2 nights in Oct 2021
Verified

10/10 Excellent

Annette F.

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

Amazing property

This was an amazing place in a great location! Pool was great!
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Katie B.

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

Great location and yard!

We loved the views of the water from the main sitting area and deck. Great proximity to the tiki bar too!
Stayed 2 nights in Sep 2021
Verified

10/10 Excellent

Carmeni G.

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

Great for families

We enjoyed our stay overall great experience the home hand everything we needed. The host was responsive at all time
Stayed 3 nights in Aug 2021

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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