Winter Retreat Near Naval Academy+ Hot Tub!

Photo gallery for Winter Retreat Near Naval Academy+ Hot Tub!

A hot tub with a view of a lake and docked boats.
An aerial view of a coastal residential area with houses, docks, and boats.
A waterfront property with a dock, sandy beach, and residential buildings.
A kitchen with wooden cabinets, granite countertops, and pendant lighting.
A waterfront property with multiple houses, a dock, and a covered area with chairs.

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Chesapeake Bay

Popular amenities

  • Hot tub on site
  • Patio
  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Refrigerator

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 9)

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Living Room 1

1 Double Sofa Bed

Office 1

2 Double Beds

Primary Bedroom

1 Queen Bed

3 bathrooms

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Shampoo

Primary Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Separate dining area
Number of living rooms
Garden
Dining area

Add dates for prices

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  • Dryer
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10.0 out of 10, Exceptional, (4 reviews)
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About the area

Annapolis

Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Annapolis Golf Club and Annapolis Landing Marina are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Travelling with kids? Consider Wild Bird Center, or check out an event or a game at Tose Family Tennis Center. Looking to get your feet wet? Kayaking, power boating and sailing adventures can be found near the property.
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Map
Annapolis, MD

What's nearby

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • U.S. Naval Academy - 15 min drive - 8.2 km
  • Annapolis City Dock - 16 min drive - 8.9 km
  • Navy-Marine Corps Memorial Stadium - 17 min drive - 10.7 km
  • Chesapeake Bay Bridge - 31 min drive - 24.8 km

Getting around

  • Odenton Station - 27 min drive
  • Fort Meade, MD (FME-Tipton) - 36 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪The Beacon Restaurant - ‬8 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Grump's Cafe - ‬5 min drive
  • ‪Jack's Fortune - ‬5 min drive

Frequently asked questions

Is Winter Retreat Near Naval Academy+ Hot Tub! pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

How much is parking at Winter Retreat Near Naval Academy+ Hot Tub!?

On-site parking is available at the property.

What time is check-in at Winter Retreat Near Naval Academy+ Hot Tub!?

Check-in begins at 4:00 PM.

What time is check-out at Winter Retreat Near Naval Academy+ Hot Tub!?

Checkout is at 10:00 AM.

Where is Winter Retreat Near Naval Academy+ Hot Tub! located?

This family-friendly Annapolis holiday home is located on the waterfront, just steps away from Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 1 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 1 out of 18 reviews

9.8/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I was privileged to spend the month of August 2026 with my daughter and her family. The home is great. Very well appointed and stocked with everything you can imagine. The deck attached to the main floor extends out over the dock and has a magnificent view. Spent many hours watching the sun set and peering out at the boat traffic. Grandkids loved crabbing off the dock and the parents and I enjoyed eating the catch. Kids also loved the beach and playground a short walk away. And, the location is great with easy access to grocery stores and a short drive to downtown Annapolis. Highly recommend this home.
Stayed 31 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Responsive hosts, beautiful home. Do not hesitate to book!
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family enjoyed staying at this home. We liked that we each had our own floor with bedroom and bathrooms. The view was very nice too. The owner was very quick in responding to our questions which I appreciated very much since it was my first time booking with VRBO.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

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

Purchaser

Beautiful stay!
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Waterfront getaway!

Beautiful house and lots of fun amenities!
Stayed 4 nights in Apr 2024
Response from VrboOwner on 7 Jun 2024
Thank you very much! Looking forward to hosting you for the next time!
Verified review

10/10 Excellent

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

Girls’ Trip

We loved our stay from the moment we opened the front door! The house was so clean, had everything we needed and the views out of the dining room and bedroom were spectacular. The dock/deck was a perfect place for old friends to spend the weekend catching up.
Stayed 3 nights in May 2025
Response from VrboOwner on 21 May 2025
Thank you so much for your kind words Rebecca! We're thrilled to hear that you and your friends enjoyed your stay and were able to relax and reconnect. It's great to know the home, views, and dock all added to a memorable weekend. We'd be happy to host you again anytime!
Verified review

10/10 Excellent

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

Naval Academy Commissioning/Graduation Week

Loved the place. Great waterfront location. Great place to relax from after a full day/week of commissioning activities. Short drive to the Naval Academy and close to all the amenities.
Stayed 6 nights in May 2024
Response from VrboOwner on 21 Sept 2024
Thank you for your review, you're group is welcome back anytime!
Verified review

10/10 Excellent

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

Amazing!

We loved our time at Sheila’s house. The view was amazing, the house was immaculate and beautifully decorated. Sheila was an outstanding host, easy to communicate with and took care of our immediate needs.
Stayed 3 nights in Mar 2024
Response from VrboOwner on 15 May 2024
So happy you all enjoyed your stay, welcome back anytime!
Verified review

10/10 Excellent

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

Wonderful property

Clean, comfortable, quiet lovely home. Great outdoor space and view. Hosts were very responsive and helpful in providing a positive experience. Pleasant neighborhood. Great for families including children and elders. Price reasonable. Well stocked.
Stayed 4 nights in May 2024
Response from VrboOwner on 21 Sept 2024
Thank for staying with us. You're all welcome back anytime!
Verified review

10/10 Excellent

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

Wonderful waterfront getaway

Beautiful home on the water with lots of natural light! Perfect for our family of 6 adults. So comfortable and inviting; the host has thought of all the small details to make your stay so enjoyable. Everything was super clean, they even provided Kcups for the coffee maker. Large deck over the water and plenty of outdoor seating to enjoy the views. Quiet neighborhood and plenty of parking. We will definitely be back for another visit!
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

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

wonderful property

My husband and I really enjoyed our stay at this beautiful house. The view is amazing from the back of the house. It was very clean and in a great location. We could easily get to Eastport and downtown Annapolis. Just be aware that there are no curtains on the master bedroom windows. This means that there is a beautiful view, but at night you need to go into the bathroom to change your clothes.
Stayed 5 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is very quaint and lovely. We loved the overall feel for a relaxing ladies trip. The beds were comfy and everything was mostly clean. A couple nuisances- the door lock kept going on and off which was a little unnerving for 3 females and the dryer didn't work and we didn't know until the clothes were washed. A few opportunities to elevate 1) make sure the hot tub is clean. It was sandy; 2) add a nespresso maker; and 3) a more comfortable and larger couch. You can literally feel the springs and the back is too low for lounging. Recommend a sectional so that 3-4 people can sit comfortably and you can do a L-shape (short facing water and long facing fireplace) to take advantage of the views as well. Ultimately enjoyed our time and was a good experience for my first time reserving. Thank you!!
Stayed 3 nights in Mar 2026
Response from VrboOwner on 31 Aug 2026
Thank you so much for your thoughtful feedback! We’re so glad you enjoyed the home and had a relaxing ladies’ getaway. We appreciate you bringing these items to our attention and have since addressed the door lock, dryer, and hot tub concerns. We’re also always looking for ways to make the home even more comfortable for our guests and appreciate your suggestions. Thank you again for staying with us, and we’d be happy to welcome you back!
Verified review

10/10 Excellent

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

Beautiful home, peaceful location

This home was as beautiful as the photos suggested and the setting was ideal for catching up with old friends in a relaxed and tranquil setting. The home has all the basic necessities in the kitchen, the beds were comfortable and we had plenty of space for three people to spread out. It would have been plenty of space even if we'd all had our spouses. I had the upstairs room. The large water-facing window made for stunning views but may not be ideal if you need a place to be pitch black when sleeping. All in all, I loved this home and the responsiveness of the host.
Stayed 2 nights in May 2024
Response from VrboOwner on 15 May 2024
Thank you so much for the review, so happy you enjoyed your stay! Thank you for being lovely guests.
Verified review

2/10 Terrible

Liked: Cleanliness, location
Disliked: Check-in, communication, listing accuracy
This rental is beautiful, the pictures match what we saw in the app. We enjoyed its proximity to the park and private beach. However, there are some serious concerns about safety. The first night we closed the two doors leading to the master bedroom and were no longer able to get in. There was no way to get in.Luckily, we had an Apple Watch, so we could call the police. We noticed a ladder behind the hot tub. We had to use the ladder to climb up the second floor balcony to get inside. This was the only way to get in; otherwise we would have to bust down one of the doors.We were lucky it was just our phones in the room, because a worse outcome could happen if someone was seriously hurt inside because we would not be able to get in to help.Otherwise the owner was very responsive when we had questions or needed help.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 11 Apr 2026
The guest herself admits the home is beautiful, matches the photos perfectly, and is in a great location, yet she has penalized our small business with a failing grade because of a situation she caused herself. To be clear for future guests: the 'safety concern' occurred when an unattended child manually locked the interior privacy latches before closing the doors. These are standard interior doors found in any family home; they do not lock on their own. We have stayed here with our own children and hosted families for years without a single lockout. Even the responding officer told us there was no emergency and that a ladder was completely unnecessary. The most disappointing part is that despite our constant, daily assistance with her many nitpicky requests and our immediate responses to her questions, she waited until after checkout to claim there was a 'design flaw.' It is deeply unfair to leave a 1 or 2-star review for a situation resulting from guest oversight rather than any property defect.
Verified review

10/10 Excellent

Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 21 nights in Sep 2024
Response from VrboOwner on 27 Oct 2024
Thank you for being great guests! Welcome back anytime!
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