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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

Photo gallery for 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

Enjoy more views from the building's top floor terrace (Pool open May-Labor Day).
Gather around the living with views of the water at Liberty Lookout.
There are charming Annapolis water views from almost every window.
The beautifully-appointed home has all new furnishings, like the King bed in the main suite.
Located in Eastport, the condo is just a short walk to Historic Annapolis and has multiple guest amenities.

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 71001 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 7)

Guest room

3 Single Beds

King Suite

1 King Bed

Living Room

1 Queen Sofa Bed

2 bathrooms

Hall

Toilet · Shower only

King Suite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms

About this property

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

Experience the Difference: Professionally Managed by iTrip Annapolis

Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location



Experience Annapolis from this beautifully-renovated 2-bedroom, 2-bath condo that feels like a luxury hotel suite. Nestled on a quiet Eastport cul-de-sac, this top-floor unit offers sweeping views of Spa Creek and downtown Annapolis. Guests enjoy access to a rooftop pool and terrace, marina, and off-street parking—all just a short walk to downtown, Eastport restaurants, yacht clubs, and marinas.



The open-concept living area features a well-equipped kitchen, dining area for 6, and a living room with water views from almost every window. The sofa converts into a Queen bed for additional guests.

Step onto the private furnished balcony to enjoy your morning coffee or sunset drinks overlooking the creek.



SLEEPING ARRANGEMENTS (Sleeps 7)

King Suite

King bed

En-suite full bathroom

Vanity area in bedroom

Flatscreen TV



Guest Bedroom

Two Twin daybeds with third pull-out Twin

Flatscreen TV

Full hall bathroom with stand-up shower



Living Room

Queen sleeper sofa (linens provided)

Access to full hall bathroom

Flatscreen TV



AMENITIES & HIGHLIGHTS

Rooftop terrace & pool (open late May–Labor Day; specific hours apply)

Marina access & water taxi nearby

Coin-operated laundry in building basement (bring quarters)

High-speed WiFi

Keurig coffee maker with starter pack

Luxury linens & starter toiletries provided

3 smart TVs

Parking for 2 cars in lot + unrestricted street parking

Secure access with elevator



PROPERTY DISTANCE TO:

Downtown Annapolis: 0.5 miles (10 min walk)

U.S. Naval Academy: 0.8 miles (15 min walk)

Washington, DC: 34 miles

Baltimore: 31 miles



HOUSE RULES:

No pets / No smoking

No parties / Quiet hours: 10pm–8am

Primary renter must be at least 25 years old

No teen or young adult groups without accompanying adult

Check-in: 4:00 PM

Check-out: 11:00 AM
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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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

No pets allowed, service animals permitted
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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 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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Annapolis

Eastport, a neighbourhood in Annapolis, is home to this condo. Kunta Kinte Plaque & Alex Haley Memorial and John Smith House are local landmarks, and some of the area's attractions include Annapolis Maritime Museum and French Soldiers Monument. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
Map
Annapolis, MD

What's nearby

  • Annapolis Harbor - 3 min walk - 0.3 km
  • U.S. Naval Academy - 9 min walk - 0.8 km
  • Annapolis City Dock - 11 min walk - 0.9 km
  • Annapolis Maritime Museum - 13 min walk - 1.1 km
  • Maryland State House - 14 min walk - 1.2 km

Getting around

  • Odenton Station - 23 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪The Choptank - ‬11 min walk
  • ‪Starbucks - ‬14 min walk
  • ‪Carrol's Creek Cafe - ‬6 min walk
  • ‪Boatyard Bar & Grill - ‬6 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬13 min walk

Frequently asked questions

Does 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free have a pool?

Yes, this property has a pool.

How much does it cost to stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

As of 27 Mar 2026, prices found for a 1-night stay for 2 adults at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free on 9 May 2026 start from £296, 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.

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 condo building is within 1 mi (2 km) of Spa Creek and U.S. Naval Academy. Annapolis Harbor and Kunta Kinte Plaque & Alex Haley Memorial are also within 15 minutes.

Reviews

10

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. 24 out of 25 reviews
Rating 8 - Good. 1 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Brian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay near everything!
Stayed 2 nights in Feb 2026
Response from VrboOwner on 2 Mar 2026
Thanks, Brian! We would love to host you again next time you’re in Annapolis. Sean, iTrip Annapolis
Verified

10/10 Excellent

Kristi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
fantastic location
Stayed 3 nights in Sep 2025
Response from VrboOwner on 1 Oct 2025
Thanks, Kristi! We’re thrilled to hear that Liberty Lookout was fantastic for your stay. It’s wonderful to know that you found the location amazing. We’re glad you enjoyed your time with us and would love to host you again next time you’re in town. Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Kacey K.

Amazing…

First time Liberty Lookout Incredible Preparation and Engagement best I have seen Location is 15 min scenic walk to Annapolis Views are amazing Amenities - restaurants and grocery stores - mins away! We will be back. Thank you!
Response from VrboOwner on 20 Dec 2025
Thanks, Kacey! We’re thrilled to hear that Liberty Lookout provided an incredible first-time experience for you. It’s fantastic that the preparation and engagement impressed you and that you enjoyed the scenic walk to Annapolis. We’re delighted to know the amazing views and proximity to restaurants and grocery stores added to your stay. We greatly appreciate your kind words and look forward to welcoming you back for another wonderful visit in the future!
From a partner site

10/10 Excellent

Great Stay

Liberty Lookout was perfect for a last minute Mom-Daughter getaway. It was clean, comfortable and a great location. Communication with the property management was helpful - thanks itrip team! See you again soon!
From a partner site

10/10 Excellent

Alli L.

Great stay in Annapolis

Liberty Lookout was all as advertised and then some. Very conveniently located to walk to downtown Annapolis, as well as Eastport. Beautiful condo, very clean and well-equipped with great views. Communication with the management company was easy, with well-documented check-in/out directions. Would definitely return!
Response from VrboOwner on 16 Oct 2025
Thanks, Alli! We’re thrilled to hear that Liberty Lookout impressed you with its convenient location, beautiful and clean accommodations, and great views. It’s wonderful to know that our communication and check-in/out process met your expectations. We hope to host you again next time you’re in town! Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Michael M.

Awesome!

Beautiful property in a great location for downtown. Well appointed and spotless. Will definitely be back again!
Response from VrboOwner on 5 Sept 2025
Thanks, Michael! We’re thrilled to hear that Liberty Lookout was a beautiful property for your stay. It’s wonderful to know that you found it well-appointed and spotless, and that the location was great for downtown. We would love to host you again next time you’re in town. Melissa~iTrip Annapolis
Verified

10/10 Excellent

Taylor W.

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

Summer Camp

As advertised. Loved the location and accomendaions.
Stayed 6 nights in Jun 2025
From a partner site

10/10 Excellent

Brian S.

Great location and view of the water

Can’t have a better location near everything in Eastport and Main St Annapolis!
Response from VrboOwner on 1 Apr 2025
Hi Brian! Thank you for being a great guest & for your positive review! We are thrilled to know you enjoyed your time in the home & we welcome you back to stay with us again anytime, Melissa~iTripAnnapolis
Verified

10/10 Excellent

Amy M.

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

Comfortable & Close to Everything

The property was exactly as pictured, and all of the furniture was quite comfortable. Plenty of towels as well, which is not always the norm when traveling. The boys enjoyed the roof top pool after long days at camp, and then we walked into town each night for dinner. Would definitely book again.
Stayed 6 nights in Jul 2025
Response from VrboOwner on 18 Jul 2025
Thanks, Amy! We're thrilled to hear that Liberty Lookout was exactly as pictured and that you found the furniture comfortable. It's great that you had plenty of towels and that the boys enjoyed the rooftop pool after their days at camp. We're glad you had the chance to walk into town for dinner each night. We would love to welcome you back for another fantastic stay in the future! Melissa~iTrip Annapolis
From a partner site

10/10 Excellent

Kim

On Liberty

The condo was perfect for us to visit and relax, close enough to walk over the bridge and get to our activities and The Yard. The condo was clean and had everything we needed for our quick trip. We had a great time visiting our Midshipman on Liberty for the weekend.
Response from VrboOwner on 28 Apr 2025
Thank you for your positive feedback Kim & we hope you will stay with us again soon! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Wayne H.

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

Great place great view great location.

Beautifully upgraded condo in a perfect location for downtown, the water, and USNA.
Stayed 2 nights in Jan 2024
Response from VrboOwner on 3 Feb 2024
Thanks, Wayne! Glad you enjoyed everything. Please come back and stay with us again! Sean, iTrip Annapolis
Verified

10/10 Excellent

Justin M.

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

Great Stay

Great condo flooded with natural light in a terrific location. My family and I enjoyed our stay while visiting our midshipman and look to return.
Stayed 2 nights in Nov 2023
Response from VrboOwner on 21 Nov 2023
Thanks, Justin!! We look forward to hosting you again next time you’re here. Sean
Verified

8/10 Good

Karen R.

The beds in the 2nd bedroom are not made for adults. They squeak with every movement. The lighting is poor. The kitchen, living room snd master bedroom are lovely. Only one key to open door into the bldg. The info needs to updated and placed in a folder. I found it accidentally on top of a shelf in the kitchen. Lovely view. Great parking. Enjoy
Stayed 19 nights in Jul 2025
Verified

10/10 Excellent

Barbara M.

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

Sailing 10/24

Absolutely perfect. Wonderful location. Beautiful property. Great staff made the weekend easy.
Stayed 2 nights in Sep 2024
Response from VrboOwner on 15 Oct 2024
Hi Barbara! 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

Lauren K.

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

Excellent host & property!

The condo is beautiful, the views are amazing, the location is great for downtown Annapolis. The host and property manager were great and super responsive with helping us out with a few questions at check in and check out. Highly recommend, will def rent here again!
Stayed 7 nights in Dec 2023
Response from VrboOwner on 27 Jan 2024
Thanks, Lauren! We look forward to hosting you again. Sean, iTrip Annapolis
Verified

10/10 Excellent

Heidi J.

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

Great time away in Eastport

I enjoyed my time in Eastport. The property was clean and close to everything. It was a quick walk into downtown Annapolis.
Stayed 2 nights in Jun 2023
Response from VrboOwner on 21 Jun 2023
Thank you Heidi for the kind review of Liberty Lookout. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified

10/10 Excellent

Leslie P.

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

Sweet spot!

Comfortable condo with wonderful views in a superb location. A must!
Stayed 2 nights in Apr 2024
Response from VrboOwner on 12 Apr 2024
Thank you for your positive review Leslie & We welcome you back anytime!
Verified

10/10 Excellent

Carolyn L.

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

Getaway

The property was outstanding in proximity to the USNA and downtown Annapolis. We were able to walk to a fabulous bakery and good restaurants. The apartment was well appointed. The King-sized bed was exceptionally comfortable. We will return to this location!
Stayed 3 nights in Oct 2024
Response from VrboOwner on 22 Oct 2024
Hi Carolyn! 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
From a partner site

10/10 Excellent

Emily P.

The Views!

The views from this condo cannot be beat! What a perfect location! To be able to walk to everything was wonderful but to also enjoy just sitting and looking at the skyline made our stay amazing. The condo itself is well furnished, stocked, and beautiful. I feel like I’ve been given a gift getting to stay here!
Stayed 20 nights in Jul 2024
Response from VrboOwner on 30 Jul 2024
Hi Emily! 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

Elaine and Rob K.

Comfortable enjoyable stay

Liberty Lookout is a fantastic condo all-around — easy parking, elevator, comfortable living spaces, amazing view, great location. Very clean and new furniture. Kitchen cookware also all new and in great shape!
Response from VrboOwner on 24 Oct 2023
Thanks, Elaine! We hope you’ll come back and stay with us again. Sean
From a partner site

10/10 Excellent

Kristi S.

Eastport

The condo was just as pictured, parking was easy, the view is stunning. Only comment is neighbor across the hall has tv on loudly all day, but once in condo, really couldn’t hear. Would definitely rent again.
Response from VrboOwner on 31 Oct 2024
Hi Kristi! 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

Sarah R.

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

perfect view

In an older apartment building, this condo is situated over the creek with views to the bridge and beyond. Everything is new and I would highly recommend.
Stayed 6 nights in Apr 2024
Response from VrboOwner on 12 May 2024
Hi Sarah! thank you for choosing us to host your stay & we welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Lindsay P.

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

Amazing Property and Location

From the property manager to the property itself, this rental and all of the amenities are a 10/10. The Eastport location provides an exquisite view of the water as well as walking distance to upscale restaurants. A 10 to 15 minute walk to downtown Annapolis as well. An unforeseen circumstance caused for us not to complete our stay but this property will be on my list for future trips to come. Go Navy!
Stayed 3 nights in Aug 2024
Response from VrboOwner on 10 Sept 2024
Hi Lindsay! 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, Go Navy! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Verified traveller

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

Slice of Annapolis Life

I lived in the Annapolis area for 2 decades in my 50s and 60s. This property is a true slice of the good life in Annapolis - upscale but family friendly location, with top-notch restaurants within walking distance (2-5 blocks) waterview with charming glimpses of the capitol dome and St Mary's church steeple, boats and paddlers going by for entertainment, boat tours and adventures nearby. The unit is newly renovated/updated, as pictured but even better in person.
Stayed 5 nights in May 2024
From a partner site

10/10 Excellent

Krissy S.

A gorgeous view and well appointed condo property

From the moment we stepped into the beautiful condo, we felt right at home. The furnishings are gorgeous and so fitting with the Annapolis theme. The kitchen and bathrooms are well stocked with any utensils and accoutrements you would need. The beds are comfortable and linens are nice. There are ample closets and dressers in the primary bedroom for storage. Although, the twin metal beds in the guest room do squeak when you shift in bed, sometimes waking the person next to you. The balcony provided glorious views of the creek, bay, bridge and historic downtown. The windows allow for natural light and views are perfect out of each window. I appreciate the automatic blinds and blackout shades which helped us overcome our jet lag and time difference coming from Hawaii. The building is well kept and parking accommodations are easy. The rooftop pool offers 360 views of town and a refreshing respite in the afternoon when it is open. It has plenty of lounge chairs for relaxing and cafe style table and chairs to enjoy a bite to eat. It even has an on staff lifeguard. The building tenants are friendly and helpful and offer great local advice and hospitality. This is a lovely bonus. The communal laundry was a great convenience for longer stays. The location cannot be beat! Walkable to all the great Eastport restaurants and downtown Annapolis. Also next to Burnside Park and easy access to the water. All in all, the condo was in pristine condition with comfortable and nautical chic decor. would definitely stay here again. We very much enjoyed the views and the unit. Can’t wait to come back! Mahalo- Krissy Snyder Kailua, Hawaii ***Side note: the neighbors across the hall may be hard of hearing. They blast Fox News all day long on high volume. It does bleed through the walls especially when you are in the primary suite. Not sure there is much you can do about the volume or noise but it was the only drawback to the unit.
Stayed 7 nights in Jun 2024
Response from VrboOwner on 12 Jul 2024
Hi Kristin! Thank you for allowing us to host your stay & for sharing your positive feedback! You are a wonderful guest &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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