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Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Photo gallery for Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

A grassy backyard with a hammock, chairs, and a boat on the water.
A room with a wooden table, a chair, a lamp, a wicker basket, and a patterned rug.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining table.
A two-story house with a front porch and a small garden area.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden table.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Annapolis Landing Marina

Popular amenities

  • On beach
  • Balcony
  • Barbecue
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen

Explore the area

View map
Annapolis, MD
  • Place, Annapolis Sailing School
    ‪3 min walk‬
  • Place, Annapolis Landing Marina
    ‪11 min walk‬
  • Place, Sparrows Beach
    ‪19 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪55 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Family Room

1 Double Sofa Bed

Main floor

1 Queen Bed

Upstairs Queen

1 Double Bed

Waterfront King

1 King Bed

2 bathrooms, 1 half bathroom

2nd Floor Hall Bath

Bathtub · Toilet · Shower only

Main Floor Full Bath

Bathtub or shower · Toilet

Outside Shower

Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Balcony
Number of living rooms
Garden

Add dates for prices

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About the area

Annapolis

Located in Annapolis, this cottage is on the beach. Wild Bird Center and Annapolis Maritime Museum are local attractions and those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
View more Cottages in AnnapolisOpens in a new window
Map
Annapolis, MD

What's nearby

  • Annapolis Sailing School - 3 min walk - 0.3 km
  • Annapolis Landing Marina - 11 min walk - 1.0 km
  • Sparrows Beach - 19 min walk - 1.6 km
  • U.S. Naval Academy - 21 min drive - 8.0 km
  • Annapolis City Dock - 22 min drive - 8.7 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪The Choptank - ‬10 min drive
  • ‪The Beacon Restaurant - ‬4 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪Royal Farms - ‬9 min drive
  • ‪Middleton Tavern - ‬10 min drive

Frequently asked questions

Is Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly on 11 January 2027 start from NZ$2,636, 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 at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?

On-site parking is available at the property.

What time is check-in at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?

Check-in begins at 4:00 PM.

What time is check-out at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?

Checkout is at 11:00 AM.

Where is Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly located?

Nestled on the beach, this Annapolis cottage is within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina. Sparrows Beach and Carrs Beach are also within 3 miles (5 km).

Reviews

9.8

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. 41 out of 45 reviews
Rating 8 - Good. 3 out of 45 reviews
Rating 6 - Okay. 1 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay at this fantastic property.
Stayed 8 nights in Aug 2026
Response from VrboOwner on 20 August 2026
Thanks, Ross. Please come back and stay with is again any time.
From a partner site

10/10 Excellent

Love Oh Happy Bay

Second year staying here and absolutely love this place! The private beach is fantastic for all our grandchildren to play and swim.
Verified review

10/10 Excellent

Liked: Location
Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back.
Stayed 2 nights in May 2026
Response from VrboOwner on 5 May 2026
Thanks, Brian! We appreciate your business and hope to host you again soon. Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location for a relaxing weekend with our dogs and midshipman!
Stayed 2 nights in Sep 2025
Response from VrboOwner on 1 October 2025
Thanks, Celine! We’re thrilled to hear that Oh Happy Bay was excellent for your relaxing weekend. It’s wonderful to know that the location was perfect for you, your dogs, and your midshipman. We’re glad you enjoyed your time with us and would love to host you again next time you’re in town. Melissa~iTrip Annapolis
From a partner site

8/10 Good

Weekend trip

Great waterfront location, with nice beach and waterside screened porch-perfect for dinning.
Response from VrboOwner on 14 August 2025
Thanks, Chris! We’re thrilled to hear that Oh Happy Bay was a great waterfront location and that you enjoyed the nice beach and waterside screened porch for dining. We would love to host you again next time you’re here. Melissa~iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I really wouldn’t classify the property as 2 1/2 bath. Two full baths would be more correct. The view was fabulous. Unfortunately for us, a family of geese did also! Made the backyard on the last day and next morning unusable. Kitchen was great and the upstairs master had the best views!
Stayed 4 nights in Apr 2026
Response from VrboOwner on 5 May 2026
Thanks, Ferne! We appreciate you and hope you’ll come back and stay with us again. Sean
Verified review

10/10 Excellent

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

Great place

Really like this place
Stayed 4 nights in Aug 2024
Response from VrboOwner on 27 August 2024
Thank you for staying with us, Scott & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Wonderful stay!

Great location! Beautiful home!
Stayed 2 nights in Oct 2023
Response from VrboOwner on 19 October 2023
Thank you Lisa for your review of Oh Happy Bay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the quintessential seaside home that novels are written about. The home has a story in every room. The views are spectacular especially from the recently renovated master suite upstairs. The bed was very comfortable and the spaciousness allowed for working and yoga. There was plenty of storage in all the nooks and crannies leading to a master bath that has been recently renovated while keeping the charm of the home. The kitchen was beautiful, clean, functional, thoughtfully designed and a joy to cook in. We enjoyed meals inside at the large family table overlooking the water as well as outside in the screened in gazebo. The sandy beach was perfect for my two little grandsons who came to visit while we were there. The short distance to downtown was perfect for making multiple trips per day if needed. I would highly recommend this property.
Stayed 5 nights in May 2026
Response from VrboOwner on 22 May 2026
Thanks, Mary!! So glad you enjoyed this home. We hope to host you again soon! Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing views with great amenities. I prefer no pets and wasn’t aware it was pet friendly.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 4 November 2025
Thanks, Joni! We’re delighted to hear that Oh Happy Bay provided amazing views and great amenities for you. We hope to have the opportunity to host you again! Melissa~iTrip Annapolis
Verified review

10/10 Excellent

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

Absolutely lovely Beachside getaway

My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!
Stayed 6 nights in Sep 2024
Response from VrboOwner on 11 November 2024
Hi Elizabeth! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Absolutely beautiful

Very family friendly with a cute little beach. Perfect get away place with lots of character.
Stayed 4 nights in Dec 2023
Response from VrboOwner on 4 January 2024
Thanks, Julie. We would love to host you again - please reach out next time you’re planning another trip to Annapolis. Sean, iTrip Annapolis
From a partner site

10/10 Excellent

Perfect place to stay

Lovely, cozy cottage with everything we needed at a beautiful, peaceful location. Gorgeous views - loved the ducks and osprey hanging out in the yard. Also, very convenient to shopping, grocery stores and downtown Annapolis.
Response from VrboOwner on 30 March 2024
Thank you for allowing us to host your stay Nicole & we welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Incredible stay

We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting.
Stayed 2 nights in May 2025
Response from VrboOwner on 3 June 2025
Hi Anthony! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Week in Annapolis

We had an amazing time this week! Would book this place again and hopefully will have the chance to do so. Very comfortable and absolutely fantastic location!
Stayed 5 nights in Jul 2023
Response from VrboOwner on 3 August 2023
Thank you Leslie for your kind review of Oh Happy Bay. We are pleased to hear you enjoyed your stay. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

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

Sailing Weekend.

Had a great weekend. Place was perfect for us.
Stayed 4 nights in Jun 2024
Response from VrboOwner on 6 July 2024
Thank you for staying with us Thomas & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
From a partner site

10/10 Excellent

Comfort Right on the Water

We absolutely loved this house and would love to book again. The little sandy beach was perfect for our granddaughter, the screened-in gazebo with large table was great for picking crabs, and the view from the primary bedroom upstairs was spectacular. The house was clean, comfy, and well stocked. A little gem!
Response from VrboOwner on 13 September 2025
Thanks, Shelley! We’re thrilled to hear that Oh Happy Bay was perfect for your stay. It’s wonderful to know that you and your family enjoyed the little sandy beach, the screened-in gazebo for picking crabs, and the spectacular view from the primary bedroom. We’re delighted that you found the house clean, comfy, and well stocked. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Great House

Our arrival was seamless and entry was easy, The house is terrific and the location is amazing! We are truly enjoying our time here!
From a partner site

10/10 Excellent

Great stay by the bay!

Everything was perfect. You couldn’t Sk for a better home and location. The deer who visited us daily was an added touch!
Stayed 6 nights in Jun 2023
Response from VrboOwner on 24 October 2023
Thanks, Kim! Please come back and stay with us again any time. Sean
From a partner site

10/10 Excellent

Hidden gem right by Annapolis!

Super clean and well furnished home with amazing waterfront views. Private beach, and kayak/paddle board access right on site. Owners and property manager were responsive and polite. Great stay!
Response from VrboOwner on 24 October 2023
Thanks, Hilary, for the great feedback. Come back and stay with us again any time! Sean
Verified review

10/10 Excellent

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

Cousins Trip to Chesapeake Bay

The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!
Stayed 2 nights in Mar 2024
Response from VrboOwner on 25 March 2024
Thanks, Monica! We look forward to hosting you again next year. Sean, iTrip Annapolis
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great. House and proximity to the water were tremendous. Only difficulty was the access to the water taxi. The water taxi stops near the house were either closed or harder to get to than expected.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 19 September 2025
Thanks, Jeffrey! We’re thrilled to hear that Oh Happy Bay was perfect for your stay. It’s wonderful to know that you enjoyed the house and its proximity to the water. We apologize for the inconvenience with the water taxi access and appreciate your feedback. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified review

10/10 Excellent

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

Rest & relaxation getaway

We had a great extended weekend here! The weather and scenery were perfect for some needed R&R with friends. The house was cozy and clean, and we really enjoyed the quiet, lovely location. It was close to everything and also an escape from the hustle and bustle.
Stayed 3 nights in Feb 2024
Response from VrboOwner on 29 February 2024
Thank you Penny for allowing us to host your stay & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Heavenly Haven

I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed
Stayed 3 nights in Aug 2024
Response from VrboOwner on 3 September 2024
Hi Marianne! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
Verified review

10/10 Excellent

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

Christmas trip

We enjoyed a Christmas away from home at this lovely property. We were so happy with our stay! The home was even better than we expected. It was warm and well cared for. The view was amazing. Our dog loved swimming in the bay. We will definitely stay again.
Stayed 4 nights in Dec 2023
Response from VrboOwner on 2 January 2024
Thanks, Denise. We welcome you and your dog back any time! Sean, iTrip Annapolis
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