Experience the charm of Eastport at Third Time's the Charm, where a beautifully manicured backyard with a firepit and private deck invites relaxation. Enjoy luxury linens, stainless-steel appliances, and dedicated workspace within this comfortable home.
Reviews
9.89.8 out of 10
Exceptional
Entire home
2 bedrooms2 bathrooms109 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Outdoor space
Add dates for prices
About this property
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Experience the Difference: Professionally Managed by iTrip Annapolis
Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis
This beautiful home is located in Eastport, just across the Spa Bridge from Historic Annapolis. Enjoy the convenience of walking to marinas, yacht clubs, restaurants, shops, and the new Eastport Brewpub. Take a stroll along the waterfront or use the water taxi to explore the harbor.
Interior Features:
Living Room: Relax in the comfortable living room with hardwood floors and a flat-screen TV.
Kitchen & Dining: The recently renovated open kitchen features a breakfast bar, adjacent dining area, and sliding glass doors leading to a large deck.
Outdoor Space: Enjoy the manicured backyard, complete with a private deck, patio, firepit, and cornhole set.
Bedrooms:
Two Queen Bedrooms, each Sleeps 2, on the second floor with luxury bedding, sharing the full bath.
Additional Sleeping Arrangements: Queen sleeper sofa in Living room
Highlights:
Private fenced backyard, patio deck and covered front porch
Firepit with Adirondack chairs and cornhole
Gas grill (propane included)
Stainless-steel appliances including beverage fridge
WiFi, big-screen TV, and luxury linens
Dedicated work space
Starter pack of toiletries, cleaning supplies, and essentials
Washer & dryer
U.S. Naval Academy: 1.5 miles
Washington, D.C.: 30 miles
Baltimore: 25 miles
House Rules:
No smoking, parties, pets or events
Must be 25+ to book
Check-in: 4:00 pm | Check-out: 11:00 am
Property amenities
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Dishwasher
Hob
Microwave
Oven
Refrigerator
Bedrooms
2 bedrooms
Bathroom
1.5 bathrooms
Hair dryer
Shampoo
Shower
Living spaces
Living room
Entertainment
TV
Outdoor areas
Barbecue grill
Firepit
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Service animals only (pets not allowed)
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Things to do
Bicycle parking
Bicycle storage
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed (service animals welcome)
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.
About the area
Eastport, a neighbourhood in Annapolis, is home to this holiday home. The area's natural beauty can be seen at Jonas Green State Park and Sandy Point State Park, while Annapolis Maritime Museum and The Colonial Players are cultural highlights. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting. Visit our Annapolis travel guide
Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?
No, only service animals are welcome at the property.
How much is parking at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
On-site parking is available at the property.
What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Check-in begins at 4:00 PM.
What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Checkout is at 11:00 AM.
Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free located?
Located in Eastport, this holiday home is within 1 mi (2 km) of Annapolis Harbor and U.S. Naval Academy. Annapolis Maritime Museum and Spa Creek are also within 10 minutes.
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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
There was trash in upstairs bathroom and insects flying about in living room that we were able to kill with rolled up paper towels.
Jeannie M.
Stayed 3 nights in Dec 2024
From a partner site
10/10 Excellent
14 Oct 2025
Great Stay
Nice location for the boat show. We enjoyed the back deck. The interior was comfortable and the kitchen was fully equipped. The property was clean and the management had good communication. Thank you.