Scenic One-Level Waterfront Retreat Mins to Annapolis w Panoramic Bay/Bridge Views & Fenced-In Yard

Annapolis, Maryland
$576 avg/night
Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

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

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • BEACH

    On The Beach
  • 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 Day Bed Sofa Bed
  • GENERAL

    Unit Size: 1340 Sq Ft (124 Sq M)
  • KITCHEN

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

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Garden Outdoor Furniture Patio Yard
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Free Toiletries Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Kayak On Site
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    Near The Ocean On The Waterfront
  • 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 : 8

Map Map

School District Availability

Review Review

  • Jessica B.

    Submitted Sep 14, 2025

    Stayed Sep 12, 2025

    Quiet but close to the water & a great location. Need some upkeep of the showers & remind folks to bring bug spray if not provided

  • Song S.

    Submitted Aug 24, 2025

    Stayed Aug 21, 2025

    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.

  • Fossett M.

    Submitted Jun 28, 2025

    Stayed Jun 23, 2025

    Great location and great neighborhood for family, even the pup!

  • Kathleen R.

    Submitted Oct 20, 2024

    Stayed Oct 18, 2024

    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.

  • Karen C.

    Submitted Jul 24, 2024

    Stayed Jul 18, 2024

    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.

  • Submitted Jul 5, 2024

    Stayed Dec 31, 1969

    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!

  • Linda

    Submitted Jul 1, 2024

    Stayed Dec 31, 1969

    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!

  • ira c.

    Submitted Jun 30, 2024

    Stayed Jun 20, 2024

    Small family friends with multiple dinners in Annapolis. Great sunrises

  • Desiree

    Submitted May 27, 2024

    Stayed Dec 31, 1969

    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!

  • james m.

    Submitted Apr 6, 2024

    Stayed Mar 23, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$576+
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