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Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard

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Welcome to the picturesque Bay Cottage, located just minutes to downtown Annapolis.
Enjoy Bay Cottage's newly-furnished gathering room!
Gorgeous views of the Bay and Bay Bridge from the front wrap-around patio at Bay Cottage.
Host a family dinner around the dining room table, with water views and seating for 6-8 people.
The kitchen is fully stocked to cook a gourmet meal!

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 81340 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a map
Annapolis, MD
  • Place, Maryland Quiet Waters Park
    ‪5 min drive‬
  • Place, Bay Bridge Market Place Shopping Center
    ‪5 min drive‬
  • Place, Bay Ridge Beach
    ‪6 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

En Suite Guest Room

1 Queen Bed

King Bedroom

1 King Bed

Living Room

1 Queen Sofa Bed

Twin Guest room

2 Single Beds

2 bathrooms

Hall Bath

Bathtub or shower · Toilet

Master En Suite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms
Garden

About this property

Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard

Experience the Difference: Professionally Managed by iTrip Annapolis

Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks!



Escape to a tranquil waterfront retreat with stunning views of the Chesapeake Bay and Bridge! This spacious one-level home is nestled on a private street in a water-privileged community just outside Annapolis, perfect for families and couples seeking relaxation. Book your serene Chesapeake Bay escape today and make unforgettable memories!



Highlights You'll Love:

Sunroom: Walls of windows for sunrise coffee & happy hour views

Outdoor Living: Fenced yard, fire pit, wrap-around deck, charcoal grill

Kayaks Included: Launch from a nearby small beach

Community Perks: Crabbing pier, playground, basketball court, larger beach



Sleeping Arrangements (Sleeps 8):

Primary Suite: Queen bed, en suite bath, flat-screen TV

King Room: Shared hall bath, flat-screen TV

Twin Room: Twin daybed + trundle (2 twins), shared hall bath

Living Room: Queen sleeper sofa



Extras & Amenities:

2 adult kayaks + fillet

Flat-screen TVs in living room & bedrooms

High-speed internet & WiFi

Dining table for 6–8

Full-size washer/dryer

Small dogs (under 30 lbs) welcome ($150 pet fee per dog)

Driveway parking for 2+ cars

Pack-n-Play available (assemble at own risk)

Accessibility ramp to deck



Prime Location:

Downtown Annapolis – 4 miles

U.S. Naval Academy – 5 miles

DC – 35 miles | Baltimore – 20 miles



Starter pack: toiletries, coffee, paper goods, cleaning essentials

Beds made with freshly-laundered linens & towels



House Rules:

At least one guest must be 25+

No smoking, parties, or events

Quiet hours: 9pm–8am

Check-in: 4:00 pm | Check-out: 11:00 am

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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Miscellaneous
Waterfront home: history, nature and comfort
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
Waterfront home: history, nature and comfort

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
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Pets

Pets allowed
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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
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
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

Frequently asked questions

Is Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard?

As of 31 Mar, 2026, prices found for a 1-night stay for 2 adults at Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard on 23 Jun, 2026 start from S$621, 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 Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard?

On-site parking is available at the property.

What time is check-in at Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard?

Check-in begins at 4:00 PM.

What time is check-out at Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard?

Checkout is at 11:00 AM.

Where is Scenic Waterfront Retreat Close to Annapolis | Panoramic Bay/Bridge Views & Fenced-In Yard located?

Nestled on the beach, this Arundel on the Bay holiday home is just steps away from Chesapeake Bay and Northern Chesapeake Bay. Maryland Quiet Waters Park and Bay Bridge Market Place Shopping Center 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. 20 out of 23 reviews
Rating 8 - Good. 3 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

9.4/10

Check-in

9.8/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

From a partner site

8/10 Good

Jessica B.

Nice & great location

Quiet but close to the water & a great location. Need some upkeep of the showers & remind folks to bring bug spray if not provided
Response from VrboOwner on 19 Sept, 2025
Thanks, Jessica! We’re glad to hear that Bay Cottage provided a quiet and great location close to the water for your stay. We appreciate your feedback regarding the showers and the reminder about bug spray. We will certainly look into these areas for improvement. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Song S.

Fantastic Stay!

We’ve stayed at this cottage twice now and it’s absolutely fantastic! A beautiful bay view location, steps away from the water front. We had a fabulous weather in Annapolis this weekend made our visit even better! Highly recommend this quiet and beautiful location in Annapolis with friendly neighbors and surroundings.
Response from VrboOwner on 29 Aug, 2025
Thanks, Song! We’re thrilled to hear that Bay Cottage was a fantastic choice for your stay once again. It’s wonderful to know that you enjoyed the beautiful bay view location and the proximity to the waterfront. We’re glad the fabulous weather in Annapolis added to your experience. It’s great to hear that you found the location quiet and beautiful, with friendly neighbors and surroundings. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified

10/10 Excellent

Fossett M.

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

Melissa

Great location and great neighborhood for family, even the pup!
Stayed 4 nights in Jun 2025
Response from VrboOwner on 4 Jul, 2025
Thanks, Melissa! We're thrilled to hear that Bay Cottage was a great fit for your family and even your pup. It's wonderful that you enjoyed the location and neighborhood. We hope to welcome you back for another fantastic stay in the future! Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Melissa K.

Great stay!

My family loved our visit to the Bay Cottage. It is such a beautiful, well-designed home. We loved the screened in porch and the beautiful view of the bay. The iTrip Annapolis team was very responsive. Would definitely stay again!
Response from VrboOwner on 5 Dec, 2022
Thank you so much for your wonderful review of the Bay Cottage. We are happy that you enjoyed your stay and would love to host your again soon.
From a partner site

10/10 Excellent

Desiree

Great accommodation!

Beautiful house that overlooks the water. Very quiet and friendly neighborhood and pet friendly. No issues during our stay and if my family and I were to come to Annapolis again I will definitely be looking here first!
Response from VrboOwner on 28 May, 2024
Thank you Desiree for sharing your happiness with your stay as well as your positive feedback! We truly enjoyed hosting you & we welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

ira c.

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

Reunion

Small family friends with multiple dinners in Annapolis. Great sunrises
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 Jul, 2024
Thank you for staying with us Ira & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Karen C.

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

Girls Family Reunion

The house is in a perfect location for exploring Annapolis and enjoying the Bay. It is bright, cheery, the decor is lovely. The kitchen well appointed. Even the knives were sharp. We enjoyed our stay very much and would stay there again.
Stayed 3 nights in Jul 2024
Response from VrboOwner on 30 Jul, 2024
Hi Karen! 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

10/10 Excellent

Sharon M.

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

relaxing and warm

very comfortable
Stayed 4 nights in Dec 2022
Response from VrboOwner on 27 Dec, 2022
Thank you for the kind review of Bay Cottage Sharon. We would love the opportunity to host you again. -Tiffany
Verified

10/10 Excellent

Cynthia B.

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

Quiet spot with a nice bay view

This property was very nice and I loved being able to hear the water outside :) We could see the Bay Bridge, cruise ships, and other boats all day so it was very relaxing. The Quiet Waters Park was also very nice and closeby.
Stayed 2 nights in Mar 2024
Response from VrboOwner on 15 Mar, 2024
Hi Cynthia! Thank you for the positive feedback & we welcome you back anytime!
Verified

10/10 Excellent

Constance P.

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

Comfortable Stay in Annapolis

Our family of 2 adults and 2 kids stayed at the cottage for an extended time in Annapolis. The home was comfortable and suited our needs well. The location was a convenient drive to the Naval Academy and the 3-season porch was ideal for working from home.
Stayed 11 nights in Jun 2023
Response from VrboOwner on 25 Oct, 2023
Thank you Constance for the kind review of Bay Cottage. Please come back and stay with us again. Safe Travels! -Tiffany
Verified

10/10 Excellent

Kathleen R.

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

Family Get-away-Weekend at Bay Cottage.

Stayed at Bay cottage to celebrate my bday with my children and grandchildren. It was a quick trip staying in a beautiful house and neighborhood. The furniture was comfortable with TVs in every room, comfortable beds and a well-stocked kitchen. Everything we needed from morning coffee to making breakfast, lunches and dinner was available, so leave all that home and enjoy your stay. We especially loved the front porch watching the sunrise and walks in the beautiful quiet neighborhood. I would recommend staying at Bay Cottage.
Stayed 2 nights in Oct 2024
Response from VrboOwner on 28 Oct, 2024
Hi Kathleen! 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
From a partner site

10/10 Excellent

Connie

Naval Academy Plebe Parents’ Weekend

We had a lovely time at Bay Cottage. It was beautifully decorated and comfortable. The view of the bay is beautiful. We plan on returning throughout our son’s four year commitment at the Naval Academy.
Verified

10/10 Excellent

Monica T.

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

My Delightful Birthday Weekend

We had an absolutely delightful time during our stay. I was particularly delighted by how close the water was, and by the nature trails sprinkled throughout the community. We were also happily surprised with the kitchen supplies as we like to cook during our vacation. The proximity to excellent restaurants was wonderful. Truly an unforgettable experience!
Stayed 2 nights in Sep 2023
Response from VrboOwner on 20 Sept, 2023
Monica, thank you so much for the kind review of Bay Cottage. We are pleased to hear you enjoyed your stay. We hope to have the opportunity to host you again. Safe travels! -Tiffany
Verified

10/10 Excellent

Alice C.

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

Just as described

Excellent property with beautiful bay view. Well stocked kitchen, bathroom and laundry room. Communication with property owner was easy.
Stayed 4 nights in Jul 2022
Response from VrboOwner on 27 Jul, 2022
Thank you Alice! We hope you come back and stay at Bay Cottage soon! - Cathy
From a partner site

10/10 Excellent

Amy F.

Great spot!

We had a great time at the Bay Cottage. The property was very clean and nicely decorated. The beds (including the pull out sofa) were very comfortable and the view is breathtaking! Lots of wildlife strolling by, including deer and foxes. The kitchen had all we needed to feel at home and the location was perfect. Peaceful, quiet and friendly neighborhood. I will definitely book this spot again the next time I am in Annapolis.
Response from VrboOwner on 9 Aug, 2022
Thank you Amy! We are so very glad you enjoyed your stay at Bay Cottage and hope that you will visit us again soon! - Cathy
From a partner site

10/10 Excellent

Linda

Loved our Bay Cottage

Was sad to leave our Bay Cottage this morning. Lovely spot. Peaceful. Clean house. Dogs loved the yard and we loved that it was fenced in so we could all relax together in between our busy schedule. Convenient location. Close to town and near services but felt remote. Loved being close to the water. Thanks for everything!
Response from VrboOwner on 1 Jul, 2024
Hi Linda! 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

10/10 Excellent

Carrie H.

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

Great water view; very clean and comfortable

The house has a great water view. The property was very clean. The kitchen had all the necessary cooking utensils and the beds were very comfortable. We enjoyed the private neighborhood beach. The property manager and owner were very responsive while we were there. There was an issue with the electronic lock on the door during our stay and the property manager was very responsive and was able to get in touch with the owner to remedy the situation as best as possible which we appreciated very much.
Stayed 4 nights in Jun 2022
Response from VrboOwner on 6 Jul, 2022
Thank you Carrie! We are so glad you enjoyed your stay at Bay Cottage, come back and visit us again! - Cathy
From a partner site

10/10 Excellent

Sufia S.

Lovely views/ Beautiful home!

We stayed here for the weekend for a girls getaway. Views LOVELY. Could have seen from the house but walked down a few feet from the home to watch the sunrise and was picture perfect. Home is very nicely furnished/ decorated. We had everything we needed for the weekend - was a huge help to have starter supplies for the kitchen and bathroom. Management was very supportive and responsive. It's a quiet residential neighborhood. There's a very small community beach in walking distance. The beds were comfortable. The sofa bed and day bed would be fine for kids, maybe not adults.
Stayed 2 nights in Jul 2022
Response from VrboOwner on 9 Aug, 2022
Thank you Sufia! We are so very glad you enjoyed the stay at Bay Cottage and we hope you come back again soon. - Cathy
Verified

10/10 Excellent

Amy W.

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

Peaceful Bay View

Lovely home with gorgeous view of the bay. We spent a lot of time on the front porch with lovely screens. Neighborhood is really quiet and in peaceful residential area. A few restaurants and grocery stores about 10-15 min away, but you’re really coming for the quiet and the views. 2nd bathroom is pretty tiny and is nested in the room with the queen bed. We made this our master. The twin/trundle was too creaky and small for our two teens, but they bunked in the other bedroom and shared the king - no problem. Lovely welcome gift and startup toiletries, paper products, and coffee. We had everything we needed!
Stayed 4 nights in Jul 2022
Response from VrboOwner on 9 Aug, 2022
Thank you Amy! We are so very glad you enjoyed our stay at Bay Cottage and hope you will visit us again! - Cathy
Verified

10/10 Excellent

Erin R.

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

Perfect getaway for 5

We brought our daughter who is in a wheelchair and a few friends for a weekend getaway and the house was accessible, the neighborhood was lovely, and the view is breathtaking. Seriously, the photos do not do the view justice. So many great places, too--indoor porch, outdoor seating, to take in the view. An fyi for accessibility--the ramp may be a bit steep for manual wheelchairs and there are a few door lips and heavy doors, but the setup worked great for us, especially the day bed for our daughter. The kitchen is actually really well stocked in terms of pots, pans, and utensils. Plan to bring staple pantry items that you might need and do not under any circumstances get takeout from Pit Boys. Would highly recommend this place as it was so clean and comfortable and the property managers were great!
Stayed 3 nights in Jun 2022
Response from VrboOwner on 28 Jun, 2022
Hello Erin, Thank you so much for your glowing review! We are so very glad it all worked out for you. Please come back and stay anytime! - Cathy
Verified

8/10 Good

james m.

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

Nice house but inaccurate description

House overall is fine. We booked because it advertised a hot tub. Upon arrival no hot tub, owner said never had a hot tub and a VRBO glitch they are aware of. Sent them screenshot of our reservation that showed hot tub and they said contact VRBO. Contacted VRBO and they said they would look into it. Never heard back. Using another service from now on.
Stayed 3 nights in Mar 2024
Response from VrboOwner on 9 Apr, 2024
James - I’m not sure why anything in Vrbo ever showed a hot tub. If we had one, we certainly would have featured it in a photo or two. In any case, we’re sorry for that misunderstanding. Sean, iTrip Annapolis
Verified

8/10 Good

Christina P.

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

Girls’ Long Weekend Reunion

We all really enjoyed our stay at Arundel on the Bay. The home is cute and very nicely furnished as a beach house. The beds, linens and towels are clean and comfortable, the kitchen is well-equipped and the bathrooms are well appointed and large enough. The neighborhood is quiet, scenic and lovely. Good proximity to kayaking, SUP etc at Ellen Moyer Park as well as Annapolis for the waterfront, history, shopping and some great food. There are a few things that could be improved, though I would certainly come back and do recommend this property. 1- From the moment we arrived there were more than a few little black ants in the dining room and kitchen that persisted for the duration of our stay. We looked for ant traps and did not find any. There seemed to be many on the front porch step area as well. Maybe weather related? **Our visit was quite brief so we did not complain to management -I have no doubt that they would have been responsive had we done so. TIP: Store any and all open food in the fridge! The ants didn’t bite so we were just careful with open food containers, crumbs and good kitchen clean up. 2- The 2 kayaks were pretty inaccessible. No idea how we would have gotten those heavy kayaks from way back behind the house to the waterfront. Some explanation would have been great. Also exactly where to launch. Some areas are “public” for the neighborhood association members but many waterfront areas are private. We did not have any badges or “guests of” IDs so did not know whether we could access the nearest gated beach. The farther one at the other end/tip seemed ok for us to access. The pier seemed to have a gate code which we did not have. 3- The fees are excessive: the 2 separate “processing fees” and others added up to A LOT for a 4 night stay! Local taxes etc are one thing, but these extra fees was truly excessive. * This may be a VRBO issue and not individual property owner/manager issue. I do not know. Overall a great location, lovely comfy home, really fun stay. Brief long weekend visit, enjoyed Annapolis and the neighborhood and were busy and outdoors enough that these issues did not detract from our stay. We would love to come back!
Stayed 4 nights in Aug 2022
Response from VrboOwner on 8 Sept, 2022
Hello Christina I wish you would have reached out to us for the ants and the beach and kayak questions. We would have been more than happy to help you out! Please do come back and visit us again! Cathy
From a partner site

10/10 Excellent

Great home

We had an amazing vacation at Bay Cottage! The house was clean, comfortable and well equipped for our needs. We loved the waterfront access and that we got to bring our golden doodle. This house is next to a pretty trail that winds through the neighborhood and we found a few community spaces to explore. The porch and the outdoor sitting area with BBQ were a highlight of the property. iTrip was great to work with and they were responsive to questions. Thank you!
Response from VrboOwner on 12 Jul, 2024
Hi Liz! Thank you for allowing us to host your stay & for sharing your positive feedback! We welcome you back to stay with us again, anytime! Melissa~iTipAnnapolis

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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