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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

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Situated on a quiet street in West Annapolis, the home is walkable to shops, restaurants and Navy Stadium.
Gather around the beautifully decorated living room at Captain's Crossing (non-working decorative fireplace).
There is seating for 6 around the dining room table.
The King bedroom suite is on the first floor, making it accessible for all guests.
The fully-renovated kitchen has all new appliances and fixtures.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2 bathroomsSleeps 61550 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Annapolis, MD
  • Place, Navy-Marine Corps Memorial Stadium
    ‪17 min walk‬
  • Place, U.S. Naval Academy
    ‪17 min walk‬
  • Place, Annapolis City Dock
    ‪4 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪29 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

1st Floor Suite

1 King Bed

2nd Floor King

1 King Bed

2nd Floor Queen

1 Queen Bed

2 bathrooms

First Floor Master En Suite

Bathtub or shower · Toilet

Second Floor King Guest

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden

About this property

Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard

Experience the Difference: Professionally Managed by iTrip Annapolis

Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan feel", from its original oak floors to the welcoming living/dining room great room. There is a first floor guest suite with a King bed, full bath, flat screen TV and private exit to the furnished deck and private, treed backyard.



Head upstairs to the 2 bedrooms and full bath. The spacious first bedroom has a King bed, desk and a full bath to share with the 2nd bedroom. The 2nd guest room upstairs is across the hall and has a fluffy Queen bed. A few blocks away, on Tucker St, enjoy scenic water views, launch your kayak, or power boat. Bike, walk, or sight see through the quaint shops of West Annapolis, the Navy-Marine Corps Memorial Stadium, downtown Annapolis, Ego Alley, Naval Academy.



Inquire about extended stay opportunities!



SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 6:

1st Floor Suite:

- King Bed

- En Suite Full Bath with bathtub/shower combo

- Flat screen TV

- Private exit to back deck and yard



2nd Floor King Suite:

- King Bed

- Desk and chair

- Flatscreen TV

- En Suite Full Bath with stand-up shower



Queen Guestroom:

- Queen Bed

- 2nd floor

- Full Bath right inside the King bedroom across the hall



HIGHLIGHTS:

- Big back deck

- Parking for multiple cars on the parking pad and street

- Private back yard

- Propane BBQ grill

- Full gourmet kitchen

- Dining room table seats 6

- WiFi

- 3 Flatscreen TVs

- Washer/dryer in the home

- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service

- Contactless entry. Drive straight to your rental home and enter using a door code we will email you. Prior to your visit, we will send you an electronic code for the lock.



Property Distance to:

- Navy-Marine Corps Memorial Stadium - .7 miles

- U.S. Naval Academy – 1.5 miles

- Washington, DC – 30 miles

- Baltimore - 30 miles



* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.

* All beds are ready made for you with freshly-laundered sheets & towels.



House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Check-in time: 4:00 pm

Check-out time: 11:00 am

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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  • Washing machine
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10.0 out of 10, Exceptional, (42 reviews)
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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
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Smoking

Smoking is not permitted

Important information

You need to know

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

Frequently asked questions

Is Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard?

As of 1 Apr, 2026, prices found for a 1-night stay for 2 adults at Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard on 29 Nov, 2026 start from S$863, 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 Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard?

On-site parking is available at the property.

What time is check-in at Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard?

Check-in begins at 4:00 PM.

What time is check-out at Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard?

Checkout is at 11:00 AM.

Where is Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard located?

Located in West Annapolis, this holiday home is within 1 mile (2 km) of Helen Avalynne Tawes Garden, Navy-Marine Corps Memorial Stadium and Peters Cove. St. John's College and U.S. Naval Academy are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 20 out of 22 reviews
Rating 8 - Good. 2 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Beth M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was easy to check in. The rooms were comfortable. The location is great for DTA. Close to everything!
Stayed 4 nights in Dec 2025
Response from VrboOwner on 19 Dec, 2025
Thanks, Beth! We’re thrilled to hear that Captain’s Crossing provided a comfortable stay for you. It’s fantastic that you found the location ideal for exploring the downtown Annapolis area. We greatly appreciate your kind words and look forward to welcoming you back for another great visit in the future!
Verified

10/10 Excellent

Jim V.

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

great stay!

Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!
Stayed 4 nights in Oct 2024
Response from VrboOwner on 22 Oct, 2024
Hi Jim! 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

Lisa P.

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

Wonderful stay

We loved staying at Captains crossing, great location and Sean was responsive and easy to work with!
Stayed 5 nights in Jul 2024
Response from VrboOwner on 16 Jul, 2024
Hi Lisa! Thank you for allowing us to host your stay & for sharing your positive stay experience! We welcome you back anytime, Melissa~iTripAnnapolis
Verified

10/10 Excellent

Will R.

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

Location, Location, Location

Perfect location close to town, but quiet and easy.
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 Jul, 2024
Thank you for staying with us Will & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Pam B.

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

Excellent home

Wonderfully convenient home to visit USNA!
Stayed 5 nights in Nov 2023
Response from VrboOwner on 21 Nov, 2023
Thanks, Pam. Please come back and stay with us again next time you’re here. Sean
Verified

8/10 Good

Myles S.

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

Annapolis Visit

We stayed at the house for two midweek nights. Accommodation is perfect for a small family of four and the property and amenities are exactly as advertised. The check-in was seamless, the historical district is 10mins by car and we loved walking around the town. The house was very clean and neat and met our expectations.
Stayed 2 nights in Apr 2025
Response from VrboOwner on 3 Jun, 2025
Hi Myles! 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

Alexandra H.

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

Awesome place to stay in Annapolis

Extremely clean. Would definitely recommend to a friend. Within walking distance to a very cute coffee shop and close to downtown Annapolis.
Stayed 2 nights in May 2024
Response from VrboOwner on 26 May, 2024
Hi Alexandra! We are very happy to hear you enjoyed your stay & we welcome you back anytime! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Courtney S.

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

Family Wedding Weekend

The house was a nice place for family members to hang out between wedding events. Great location near the Naval Academy and Waterfront.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 17 Sept, 2024
Hi Courtney! 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

Lori M.

Cozy Home

Cute home in lovely quiet neighborhood. We were in town for commissioning week. Location was perfect for walking to the ceremony at Navy-Marine Corps Memorial Stadium. Home of was very comfortable.
Response from VrboOwner on 28 May, 2025
Hi Lori! Thank you for being a great guest & we welcome you back anytime! We're thrilled to hear that Captain’s Crossing was perfect for your stay during commissioning week and that you enjoyed the convenient location for walking to the ceremony. We look forward to hosting you again on your next trip! Melissa~iTripAnnapolis
Verified

10/10 Excellent

Rachel O.

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

Excellent

Lovely house.
Stayed 3 nights in Nov 2024
Response from VrboOwner on 3 Dec, 2024
Hi Rachel! 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

Daniel R.

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

Lovely and Relaxing

This house was just lovely. Very clean. Very convenient to downtown Annapolis and restaurants. Since it rained 4 days out of five, a few games in the house would have been helpful. Would be perfect for a small family or a few friends.
Stayed 5 nights in May 2025
Response from VrboOwner on 3 Jun, 2025
Hi Daniel! 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

Judie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was very comfortable for 4 adults. The location was perfect, a quiet neighborhood and walkable to restaurants, and while a long walk, downtown Annapolis is an easy walk. The common areas were comfortable, I wish we had had more time to simply enjoy the house, but it was a busy weekend of visiting friends and family. The only quirks that while worked for us, might be helpful info for planning. The bathrooms are small, very little counter space, so if you need more space this could be challenging. Also both bathrooms are in bedrooms, meaning the person staying in the 3rd bedroom needed to go into the other bedroom. Again, this was fine for the group we were traveling with.
Stayed 2 nights in Dec 2025
Response from VrboOwner on 30 Dec, 2025
Thanks, Judith! We're delighted that Captain’s Crossing provided a comfortable stay for you and your group. It's wonderful to hear that you enjoyed the quiet neighborhood and found the location so convenient for walking to restaurants and downtown Annapolis. We appreciate your feedback on the bathroom setup and size; it's helpful for future guests to know. We look forward to welcoming you back for another enjoyable visit, hopefully with more time to relax and enjoy the house! Melissa~iTripAnnapolis
Verified

10/10 Excellent

David S.

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

Perfect spot!

Great location, close to downtown, easy access, and great communications. Thank you.
Stayed 4 nights in Oct 2023
Response from VrboOwner on 26 Oct, 2023
Thanks, David. We look forward to hosting you again next time! Sean
Verified

10/10 Excellent

Evan H.

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

Weekend stay for wedding in annapolis

Very nice property, not far from annapolis. Clean and up to date. I would definitely go back.
Stayed 2 nights in Jun 2024
Response from VrboOwner on 6 Jul, 2024
Thank you for staying with us Evan & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
From a partner site

10/10 Excellent

Robert F.

Capt’s Crossing

Great house to stay in during visit to Annapolis. West Annapolis a neat area and close to stadium. Easy access to downtown and mall area as well. Overall nice amenities and comfort. Thank you!
Stayed 3 nights in Dec 2023
Response from VrboOwner on 2 Jan, 2024
Thanks, Robert. Come back and stay with us again any time! Sean, iTrip Annapolis
Verified

10/10 Excellent

Robin S.

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

Great weekend house

We were in Annapolis to visit our mid and attend the Navy football game. This house was perfect for our family of 4. The location was convenient to the yard, DTA and the stadium.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 19 Oct, 2023
Robin we are pleased to hear you enjoyed Captain's Crossing. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
From a partner site

10/10 Excellent

Jean N.

Comfortable cottage

We took a girls trip to Annapolis Maryland and found this really cute, cozy cottage in our old neighbor in West Annapolis. We were thrilled to be close to everything that we wanted to see and do. We had all the comforts of home here. Wonderful place to stay, our only down fall was not having a regular coffee maker.
Stayed 4 nights in Oct 2024
Response from VrboOwner on 2 Nov, 2024
Hi Jean! 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. I will be sure to discuss your suggestion about the drip coffee maker with my team to see if we can supply that as well. Melissa~iTripAnnapolis
Verified

10/10 Excellent

kathy m.

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

Incredibly Clean!

This property was great! The house was incredibly clean! It was spacious enough for spouse and I plus two adult kids, each having their own room, yet cozy enough we were together. Loved the start up toiletries and kitchen necessities. Very easy to get to from USNA and DTA. Would highly recommend and we will definitely be staying again!
Stayed 2 nights in Sep 2023
Response from VrboOwner on 28 Sept, 2023
Thank you Kathy for your kind review of Captain's Crossing. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified

10/10 Excellent

Beth C.

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

Great place in West Annapolis

It was everything we wanted in our rental, clean, all the essentials, well organized and decorated lovely to boot! It was the attention to detail that I appreciate too like labeling the light switches. It is about 1.5 miles from the center of Annapolis but we walked and took Uber since it was nice not to have to find parking. There is a good coffee spot up the street too!
Stayed 2 nights in Aug 2023
Response from VrboOwner on 30 Aug, 2023
Thank you Beth for your kind review of Captain's Crossing. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified

10/10 Excellent

Shane L.

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

A quiet piece of heaven.

I stayed here for a week. Other than the weather did not cooperate, this week was amazing. The house has everything you would need for a one night stay to a long term stay. It has been newly renovated and the furniture, appliances, beds, and everything remind you of a quant Ralph Lauren location. Well worth the stay and I look forward to future stays here.
Stayed 4 nights in Jun 2023
Response from VrboOwner on 28 Jun, 2023
Thank you Shane for the kind review of Captain's Crossing. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels! -Tiffany
Verified

10/10 Excellent

kelly l.

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

Lovely weekend stay!

We loved the property- my husband went to the academy so we’ve been there a bunch but staying in this part of town was a first and it did not disappoint! Only negative was one night we stayed home and it was a bit loud at night with dogs barking but a sound machine and our 1 year old slept through it! Otherwise it’s a beautiful well kept property with more space than expected. There was even a neighborhood yard sale we walked around through and coffee, restaurants and icecream etc in walking distance. Would absolutely recommend!
Stayed 2 nights in Apr 2024
Response from VrboOwner on 30 Apr, 2024
Thank you for staying with us Kelly & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Verified

8/10 Good

MJ A.

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

Cute older home

Overall a nice stay... a few things to know before you book. Both upstairs and downstairs bathrooms are housed within each king bedroom. So no bathroom accessible for third bedroom guests in the middle of the night. Upstairs bathroom is "very" tiny Washer and dryer are in the unfinished cellar. Single cup brew coffee maker ..... had to wait your turn for a cup of Joe. Very easy to get a hold of manager. Clean property S
Stayed 4 nights in Jun 2024
Response from VrboOwner on 13 Jul, 2024
Hi Mj, thank you for allowing us to host your stay & we hope you still found the home enjoyable. We would be happy to host you again in the future! Melissa~iTripAnnapolis

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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