Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard
Experience the Difference: Professionally Managed by iTrip Annapolis
Walk to waterfront restaurants, hop the water taxi into downtown Annapolis, and unwind by your private fire pit—all from this charming Eastport retreat just minutes from the US Naval Academy. This professionally-decorated 2-bedroom, 1.5-bath home offers the perfect blend of comfort, location, and Eastport charm. Perfect for couples or families traveling with their pups!
Start your day with coffee on the sunny front porch, then step into the cozy living room with a large flatscreen TV and Queen sleeper sofa. The open layout leads to a stylish dining area and a fully-stocked gourmet kitchen. Step out back to your private fenced patio and deck, complete with firepit, propane grill, and café seating for 4.
Unrestricted street parking available.
Sleeps 7 | 2BR / 1.5BA
King Bedroom (upstairs)
Queen + Twin Trundle Bedroom (upstairs)
Queen Sleeper Sofa (main floor)
1 Full bath upstairs, 1 Powder room downstairs
HIGHLIGHTS
Fenced backyard with private deck, patio, firepit & grill
Front porch seating
Dining table for 4–6
Café table for 4 on deck
High-speed WiFi & large Smart TV
Washer & dryer inside the home
Dog-friendly with $150 non-refundable pet fee (per pet)
Keyless entry – check yourself in with an electronic code
Unrestricted, easy street parking
Boutique-level service with starter amenities provided: coffee, toiletries, paper products, dish soap & more
All beds are made with freshly-laundered linens & towels
Distance to:
Downtown Annapolis: 1 mile
USNA: 1.5 miles
DC: 30 miles | Baltimore: 25 miles
House Rules:
No smoking, parties, or events. One guest must be 25+. Quiet hours: 10pm–8am.
Check-in: 4PM | Check-out: 11AM
Add dates for prices
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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
About the area
Annapolis
Located in Annapolis, this holiday home is in the city centre. Annapolis Maritime Museum and French Soldiers Monument are local attractions and those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Maryland Hall for Creative Arts and Helen Avalynne Tawes Garden are also worth visiting.
Is Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard?
As of 9 May, 2026, prices found for a 1-night stay for 2 adults at Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard on 14 Mar, 2027 start from S$669, 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 Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard?
On-site parking is available at the property.
What time is check-in at Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard?
Check-in begins at 4:00 PM.
What time is check-out at Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard?
Checkout is at 11:00 AM.
Where is Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard located?
Located in Eastport, this holiday home is within a 10-minute walk of Annapolis Maritime Museum and U.S. Naval Academy. Annapolis Harbor and Spa Creek are also within 15 minutes.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Parking was easy and the place was in a perfect location!
Jesse T.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 5 May, 2026
Thanks, Jesse! We appreciate your business and hope to host you again.
Sean, iTrip Annapolis
From a partner site
8/10 Good
Heidi R.
5 Apr, 2026
Sweet Little Home
Nice location on a quiet street. Good restaurants and shops in walking distance. Layout and furnishings are well thought out. For folks with mobility or balance issues, be aware the staircase is steep. It does have a good handrail.
Thanks, George! We’re thrilled to hear that Eastport Easy provided a great location for your stay. We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
From a partner site
10/10 Excellent
MH
19 Feb, 2026
Amazing in Annapolis
The accommodations in Annapolis are great. Easy parking, clean well kept rooms, kitchen stocked with cookware so you can make your own meals. Washer and Dryer if you are visiting for an extended stay. This booking was last minute and everything has been great.
House was in a great location. Well stocked kitchen and house was clean! Thanks for a great location for our USNA reunion.
Erika T.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 4 Nov, 2025
Thanks, Erika! We’re thrilled to hear that Eastport Easy provided a great location for your USNA reunion. It’s wonderful to know that you found the house well-stocked and clean. We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
Great location… quiet friendly neighborhood. We walked to USNA. On street parking a breeze. Will definitely stay again
Brian S.
Stayed 3 nights in Aug 2025
Response from VrboOwner on 13 Aug, 2025
Thanks, Brian! We’re thrilled to hear that Eastport Easy was in a great location and that you enjoyed the quiet, friendly neighborhood. It’s wonderful to know that walking to USNA and the easy on-street parking were highlights of your stay. We would love to host you again next time you’re here.
Melissa~iTrip Annapolis
We had a fabulous stay in Eastport. The property was exactly as described and in a great location. Looking forward to our next visit!
Kerry C.
Stayed 2 nights in Jul 2024
Response from VrboOwner on 30 Jul, 2024
Hi Kerry! 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
Andrea S.
1 Jun, 2025
Eastport Easy
Great house! Wonderful, fun, walkable neighborhood.
Andrea S.
Response from VrboOwner on 4 Jun, 2025
Hi Andrea! Thank you for being a great guest & we welcome you back anytime! We're thrilled to hear that Eastport Easy provided a wonderful setting for your stay and that you enjoyed the fun and walkable neighborhood. We look forward to hosting you again on your next trip! Melissa~iTripAnnapolis
Hi Bob! 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
Clean little place in a quiet neighborhood. Walk to great local restaurants and shops.
Jeff B.
Stayed 2 nights in Jul 2023
Response from VrboOwner on 20 Sept, 2023
Thank you for the kind review of Eastport Easy. Please come back and stay with us again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Jennifer M.
21 Sept, 2025
Wonderful experience
Our stay at Eastport Easy exceeded our already great expectations. The home was as charming as it was convenient to downtown Annapolis. We easily found street parking right in front of the home which is located in a picturesque, quiet neighborhood. The backyard’s fire pit was a cozy place for us to unwind at the end of our day. The layout of the bedrooms were accommodating for our party and the beds were cozy too.
Thank you for a great stay. Until next time Eastport
Jennifer M.
Response from VrboOwner on 24 Sept, 2025
Thanks, Jen! We’re thrilled to hear that Eastport Easy exceeded your expectations. It’s wonderful to know that you found the home charming and conveniently located to downtown Annapolis. We’re glad you enjoyed the picturesque neighborhood and the cozy fire pit in the backyard. It’s great to hear that the bedroom layout and beds were accommodating and comfortable for your party. We would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
Had a 2 night visit with family. House is extremely close to Eastport marinas which was ideal for us. It was clean and comfortable with a nice outdoor space. Would absolutely visit again
Trevor T.
Stayed 2 nights in Jun 2023
Response from VrboOwner on 20 Sept, 2023
Thank you for the kind review of Eastport Easy Trevor. We are pleased to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels!
-Tiffany
We are glad you enjoyed your stay! Come back and visit us again soon! - Cathy
From a partner site
10/10 Excellent
Amy F.
13 Aug, 2023
Enjoyable Eastport Stay
Our family of three plus our Aussiedoodle enjoyed our five-day stay at Eastport Easy. The house was sparkling clean and very comfortable. The location was great, an easy walk to nice restaurants and the maritime museum. We enjoyed the fire pit, the deck, and the front porch. We would definitely recommend this as a great getaway and base for exploring all Annapolis has to offer.
Amy F.
Stayed 5 nights in Aug 2023
Response from VrboOwner on 20 Sept, 2023
Thank you Amy for your kind review of Eastport Easy. We are happy to hear you enjoyed your stay. We would love the opportunity to host you again. Safe Travels!
-Tiffany
A sweet little house in a fabulous location. We stayed here for Christmas to be close to our families, we left the area 3 years ago.
House was perfect, quiet neighbors and friendly locals. We would definitely book here again!
Courtney C.
Stayed 5 nights in Dec 2023
Response from VrboOwner on 2 Jan, 2024
Thanks, Courtney - so glad you enjoyed everything. Come back any time and stay with us again!
Sean, iTrip Annapolis
The property is very nice, clean and convenient to many Eastport sights and activities. Unfortunately it rained our entire stay so we didn’t get a chance to enjoy the cute back deck. The beds are comfortable and there is plenty of closet space.
Susan M.
Stayed 5 nights in May 2022
Response from VrboOwner on 20 Sept, 2023
Thank you so much for your kind review of Eastport Easy! We are very glad you enjoyed your stay. Please come back and visit with us again. - Cathy
Hi Steven! 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
We parked our car and never moved it for 4 days! Fun and accessible Annapolis! Walking city with easy & quick Uber rides. Restaurants. Bars, museums, music and the naval academy. Great location and comfortable for adults, dog & 2-year old.
Laurie H.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 3 Oct, 2024
Hi Laurie! 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
Kelly M.
1 May, 2024
Great s
This is a lovely townhouse in a great location! We enjoyed taking walks around the area…amazing access to coffee shops, restaurants and bars. The unit is nicely updated and well stocked. The iTrip staff was so pleasant and easy to work with. Would definitely recommend Eastport Easy!
Kelly M.
Response from VrboOwner on 2 May, 2024
Thank you for staying with us Kelly & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Tiana S.
17 Jul, 2023
Beautiful home in Eastport!
This property was truly amazing! It have everything that you may need: truly a home away from home. Short walk from Eastport restaurants and the city dock. Beautiful decor and extremely clean. Very true to the property description and photos. We enjoyed the bbq and backyard! Can’t wait to go back soon!
I rented the property for the weekend for out of town guests who were quite happy there. One drawback is that there's only one bathroom and a half bath.
david l.
Stayed 3 nights in May 2024
Response from VrboOwner on 11 Jun, 2024
Hi David- thank you for allowing us to host the stay & we welcome you back anytime! Melissa~iTripAnnapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests