Cottage in Annapolis, MD
4 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this cottage rental
(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early.
The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch.
We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.
The cottage is all yours, and its self check-in, but please reach out on the app or on Jim's cell for anything at all!
Check-in: After 4:00 PM (early check-in when available)
Check-out: 11:00 AM (late check-out when available)
Please:
No smoking
No pets
No parties or events
Quiet Hours 9 pm to 9 am
Groceries: Grauls, on Taylor Avenue. Go out to Ridgely Avenue, turn Right. Go about 3 blocks and Grauls is in the strip mall on the right. 8 minute walk.
Liquor, Beer, Wine: In the Walgreens, of all places! Same strip mall as Grauls. In the back left hand corner inside the Walgreens. Good selection of everything. Even shorter walk to Chessie's Wharf, for an amazing selection of RAR Brewing's finest drafts!
Local places to eat and drink – all within 5 minute walk - turn right at the bottom of our street, on Ridgely Avenue:
Bakery: Great Harvest baking – on Ridgely Avenue just a couple of hundred yards up on the left, just beyond the gas station. Go-to favorite: Mocha Scones
Coffee Shop: Bean Rush Café - Annapolis St. (the next street over, take a left off Ridgely on Monterey, then right on Annapolis St.
Breakfast: Evelyn’s- Annapolis St.
Dinner: In Grano, "Drawing inspiration from Italy, Japan, Spain, Greece, and beyond, In Grano’s menu promises an elevated, global dining experience."
Ice Cream: Always Ice Cream - next door to Bean Rush Café - topped Fodor's list of ice cream places in the USA! (Note: Annapolis Ice Cream Company/Always Ice Cream Named Top 12 Ice Cream Shop by Fodor's Travel!!)
West Annapolis Progressive dinner: 1) round of drafts at Chessie's wharf while you wait for your table at In Grano 2) Fine Dining at In Grano (safe space for ice cream) 3) Always Ice Cream
Pizza, Pasta: Bella Italia, in same shopping center as Grauls, at end of Ridgely Avenue (at corner of Ridgely and Taylor)
The whole place. This is a stand-alone cottage. Access to private waterfront and dock.
TV / WIFI / Netflix
Air conditioning
Fully Equipped Kitchen
Nespresso Machine or French Press, or Drip Coffee Maker
Beautiful Dining Nook
Comfy Queen with expansive Water Views , and a Comfortable Queen sofabed
Full Bath with all essential Amenities
Hair Dryer
Clothes Iron
Extra Pillows and Blankets
Screened-in Porch overlooking Weems Creek
Serene environment
Picnic area on the dock.
Fire pit on the hillside
Private Dock
Use of Stand-Up Paddle boards
Use of Canoe
Use of Kayaks
Use of 17' Boston Whaler (for experienced boaters, and at extra cost)
“Our stay at Jim’s place was perfect for a weekend away. We’ll definitely book again! – Steve, March 2021”
"We had a lovely stay at Weems Creek Cottage. It is so quaint, quiet, and thoughtful. We loved the scenery, the bedside view of the sunset over the river was stunning. We slept so well, absolute peace and immediate comfort. It’s also in a really cute area, nice little local restaurants and cafes nearby, and we enjoyed walking/driving to downtown Annapolis. Very easy to find, SO clean and very well designed, private and intimate, just really cute and charming spot. Jim was very friendly, responds immediately and provides all the information you could possibly need! We will definitely be returning in warming weather. Highly recommend!" (January, 2025)
The original 1910 cottage studio was fully refurbished with charming décor and your comfort in mind.
In addition to the studio and screened-in porch, all of our guests have access to our waterfront backyard complete with fire pit, Adirondack chairs and fantastic views of Weems Creek: the boats, the birds and the sunsets!
Be sure to walk on down to the picnic area - on our private dock! There you can decide between the paddle boards, kayaking, or taking our boat out on to the Severn River or down to City Dock for a drink or a bite! (Experienced Boaters: Reach out to us about using our 17' Boston Whaler for an extra cost )
Over the summer, the dock picnic area is also the perfect setting for your own classic Maryland Crab Feast! For the chefs and adventurous at heart, we've got all the necessary pots and mallets to give it a go yourself. If you're not up for the mess - we can definitely tell you where to enjoy a crab feast in town.
Be sure to take a quick stroll through our neighborhood to grab local delicacies at the Great Harvest Bread Co, the Bean Rush Cafe and all the rest that the village of West Annapolis has to offer. Our location is pretty amazing.
Plus, we are only a few minutes' walk to the US Naval Academy’s Gate 8, the entrance to the historic Annapolis campus and Navy-Marine Corps Memorial Stadium!
Friends, we hope you will enjoy your stay with us, and please, come again!
“I have stayed in the cottage in all 4 seasons and each has its own unique beauty. It is a great home away from home.” – Darcy, December 2021”
Short walks to many things. 1.5 miles to Annapolis City Dock. Ride sharing apps.
Pro tip: At City Dock, take the water taxi to Davis' Pub in Eastport, then do a progressive walking lunch or dinner on your way back to the city dock through Eastport, over the beautiful Spa Creek drawbridge - and back to the City Dock!
5 minutes walk to: Bean Rush Cafe/Coffee, Evelyns, Naval Bagels, RAR Brewing/Chessie's Wharf, In Grano, Positano, Always Ice Cream, Great Harvest Baking, and more.
Easy walk to the Navy stadium or St. John's College.
1.5 miles to Annapolis City Dock area or USNA Gate 1 (even closer to Gate 8)
The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch.
We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.
The cottage is all yours, and its self check-in, but please reach out on the app or on Jim's cell for anything at all!
Check-in: After 4:00 PM (early check-in when available)
Check-out: 11:00 AM (late check-out when available)
Please:
No smoking
No pets
No parties or events
Quiet Hours 9 pm to 9 am
Groceries: Grauls, on Taylor Avenue. Go out to Ridgely Avenue, turn Right. Go about 3 blocks and Grauls is in the strip mall on the right. 8 minute walk.
Liquor, Beer, Wine: In the Walgreens, of all places! Same strip mall as Grauls. In the back left hand corner inside the Walgreens. Good selection of everything. Even shorter walk to Chessie's Wharf, for an amazing selection of RAR Brewing's finest drafts!
Local places to eat and drink – all within 5 minute walk - turn right at the bottom of our street, on Ridgely Avenue:
Bakery: Great Harvest baking – on Ridgely Avenue just a couple of hundred yards up on the left, just beyond the gas station. Go-to favorite: Mocha Scones
Coffee Shop: Bean Rush Café - Annapolis St. (the next street over, take a left off Ridgely on Monterey, then right on Annapolis St.
Breakfast: Evelyn’s- Annapolis St.
Dinner: In Grano, "Drawing inspiration from Italy, Japan, Spain, Greece, and beyond, In Grano’s menu promises an elevated, global dining experience."
Ice Cream: Always Ice Cream - next door to Bean Rush Café - topped Fodor's list of ice cream places in the USA! (Note: Annapolis Ice Cream Company/Always Ice Cream Named Top 12 Ice Cream Shop by Fodor's Travel!!)
West Annapolis Progressive dinner: 1) round of drafts at Chessie's wharf while you wait for your table at In Grano 2) Fine Dining at In Grano (safe space for ice cream) 3) Always Ice Cream
Pizza, Pasta: Bella Italia, in same shopping center as Grauls, at end of Ridgely Avenue (at corner of Ridgely and Taylor)
The whole place. This is a stand-alone cottage. Access to private waterfront and dock.
TV / WIFI / Netflix
Air conditioning
Fully Equipped Kitchen
Nespresso Machine or French Press, or Drip Coffee Maker
Beautiful Dining Nook
Comfy Queen with expansive Water Views , and a Comfortable Queen sofabed
Full Bath with all essential Amenities
Hair Dryer
Clothes Iron
Extra Pillows and Blankets
Screened-in Porch overlooking Weems Creek
Serene environment
Picnic area on the dock.
Fire pit on the hillside
Private Dock
Use of Stand-Up Paddle boards
Use of Canoe
Use of Kayaks
Use of 17' Boston Whaler (for experienced boaters, and at extra cost)
“Our stay at Jim’s place was perfect for a weekend away. We’ll definitely book again! – Steve, March 2021”
"We had a lovely stay at Weems Creek Cottage. It is so quaint, quiet, and thoughtful. We loved the scenery, the bedside view of the sunset over the river was stunning. We slept so well, absolute peace and immediate comfort. It’s also in a really cute area, nice little local restaurants and cafes nearby, and we enjoyed walking/driving to downtown Annapolis. Very easy to find, SO clean and very well designed, private and intimate, just really cute and charming spot. Jim was very friendly, responds immediately and provides all the information you could possibly need! We will definitely be returning in warming weather. Highly recommend!" (January, 2025)
The original 1910 cottage studio was fully refurbished with charming décor and your comfort in mind.
In addition to the studio and screened-in porch, all of our guests have access to our waterfront backyard complete with fire pit, Adirondack chairs and fantastic views of Weems Creek: the boats, the birds and the sunsets!
Be sure to walk on down to the picnic area - on our private dock! There you can decide between the paddle boards, kayaking, or taking our boat out on to the Severn River or down to City Dock for a drink or a bite! (Experienced Boaters: Reach out to us about using our 17' Boston Whaler for an extra cost )
Over the summer, the dock picnic area is also the perfect setting for your own classic Maryland Crab Feast! For the chefs and adventurous at heart, we've got all the necessary pots and mallets to give it a go yourself. If you're not up for the mess - we can definitely tell you where to enjoy a crab feast in town.
Be sure to take a quick stroll through our neighborhood to grab local delicacies at the Great Harvest Bread Co, the Bean Rush Cafe and all the rest that the village of West Annapolis has to offer. Our location is pretty amazing.
Plus, we are only a few minutes' walk to the US Naval Academy’s Gate 8, the entrance to the historic Annapolis campus and Navy-Marine Corps Memorial Stadium!
Friends, we hope you will enjoy your stay with us, and please, come again!
“I have stayed in the cottage in all 4 seasons and each has its own unique beauty. It is a great home away from home.” – Darcy, December 2021”
Short walks to many things. 1.5 miles to Annapolis City Dock. Ride sharing apps.
Pro tip: At City Dock, take the water taxi to Davis' Pub in Eastport, then do a progressive walking lunch or dinner on your way back to the city dock through Eastport, over the beautiful Spa Creek drawbridge - and back to the City Dock!
5 minutes walk to: Bean Rush Cafe/Coffee, Evelyns, Naval Bagels, RAR Brewing/Chessie's Wharf, In Grano, Positano, Always Ice Cream, Great Harvest Baking, and more.
Easy walk to the Navy stadium or St. John's College.
1.5 miles to Annapolis City Dock area or USNA Gate 1 (even closer to Gate 8)
Amenities at Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
Non-smoking
No pets allowed
Family friendly
Map of Annapolis, MD
Ratings and reviews
10 / 10Outstanding·May 2026
This was the perfect spot- adorable home, waterfront, and close to downtown. We kayaked, enjoyed the firepit and Adirondack chairs every evening, and the host could not have been more helpful. Highly recommend.
10 / 10Outstanding·Mar 2026
Lovely location and Jim was very helpful all the way around!
10 / 10Outstanding·Jan 2026
Wow wow wow! Stay here! Host was great- very communicative and friendly. The place is right on the water, beautiful views and a comfortable place to stay. I’m sitting in the airport on my way back to Texas and already missing my little cottage by the water.
10 / 10Outstanding·Oct 2025
Jim is great to deal with! Communicates by text which makes it easy. Very willing to help with anything yet not intrusive in any way. This is a unique spot which is close to downtown Annapolis and the US Naval Academy. With a quick drive we were to all attractions and downtown area. The place has everything one needs and is comfortable also!
$$$$
Top rated by guests
10Outstanding
(91 Ratings)
"This was the perfect spot- adorable home, waterfront, and close to downtown. We kayaked, enjoyed the firepit and Adirondack chairs every evening, and the host could not have been more helpful. Highl..."
Anne P.Don't miss out! Price and availability may change
