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Parking & Pet Friendly USNA-themed Annapolis home

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Beautifully-renovated duplex on President's Hill
Lounge in the sunny private backyard and patio with a firepit!
Private Hot Tub in the fenced-in private backyard
The spacious dining room doubles as a work space.
The comfortable family room greets you!

Reviews

9.8 out of 10
Exceptional
3 bedrooms1+ bathroomSleeps 6

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Parking available

Explore the area

Map
Annapolis, MD
  • Navy-Marine Corps Memorial Stadium
    ‪12 min walk‬
  • U.S. Naval Academy
    ‪17 min walk‬
  • Annapolis City Dock
    ‪17 min walk‬
  • Washington, DC (DCA-Ronald Reagan Washington National)
    ‪50 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Front Queen

1 Queen Bed

Garden view Queen

1 Queen Bed

Middle Guest room

1 Double Bed

1 bathroom, 1 half bathroom

Main Floor Powder Room

Toilet

Second Level

Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

Parking & Pet Friendly USNA-themed Annapolis home

This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! There are multiple outdoor spaces: a welcoming front porch, back deck overlooking nice big back yard, and parking. The main floor provides plenty of hangout space with a family room, large screen TV, dining table for 6 with a separate desk space, a full kitchen, with many new appliances, and a half bath. The second level features 3 bedrooms and a full bathroom.

The back yard is large and fenced in for better privacy. There is a gas fireplace and outdoor dining table. There is also a 6 person hot tub in the private back yard. Smart TV's in each bedroom as well as the family room.

SLEEPING ARRANGEMENTS 3 BR / 1.5 BA / Sleeps 6:
Front Queen room:
- Second Floor
- Queen Size Bed

Middle Guest room:
- Second Floor
- Full Size Bed

Garden view Queen room:
- Second Floor
- Queen Size Bed

HIGHLIGHTS:
- Furnished Front Porch
- Private back deck with 6-person hot tube
- Parking for 2 cars behind the home
- Fenced in the back yard
- Full gourmet kitchen
- Dining room table seats 6
- WiFi
- Big Screen TVs
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Washer & dryer located inside the home
- Non-Smoking
- Dogs Allowed - $150 non-refundable deposit due per pet at the time of booking.
- Contactless entry. Drive straight to your rental home and enter the code to the back door that we will email to you prior to checkin.
***************
Property Distance to:
- U.S. Naval Academy – 1 mile; 15 minute walk
- Washington, DC – 30 miles
- Baltimore - 25 miles
***************
*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.
* 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/no pets unless pet deposit has been paid prior to arrival. Please respect the neighbors and neighborhood.
Check-in time: 4:00 pm
Check-out time: 11:00 am

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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  • Washer
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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

Pets allowed
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Smoking

Smoking is not permitted

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 150

We have included all charges provided to us by the property.

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

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Annapolis City Dock and Annapolis Harbor Center Shopping Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Jonas Green State Park and Sandy Point State Park. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting. With kayaking, waterskiing and water tubing nearby, you'll find plenty of adventures in the water.
Map
Annapolis, MD

What's nearby

  • Navy-Marine Corps Memorial Stadium - 12 min walk - 1.1 km
  • Maryland State House - 14 min walk - 1.2 km
  • U.S. Naval Academy - 17 min walk - 1.5 km
  • Annapolis City Dock - 17 min walk - 1.5 km
  • Anne Arundel Medical Center - 5 min drive - 4.2 km

Getting around

  • Odenton Station - 21 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪Chick & Ruth's Delly - ‬15 min walk
  • ‪Level Small Plates Lounge - ‬10 min walk
  • ‪The Red Bean - ‬14 min walk
  • ‪Annapolis Ice Cream - ‬14 min walk
  • ‪Miss Shirley's Cafe Annapolis - ‬3 min walk

Frequently asked questions

Is Parking & Pet Friendly USNA-themed Annapolis home pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Parking & Pet Friendly USNA-themed Annapolis home?

Check-in begins at 4:00 PM.

What time is check-out at Parking & Pet Friendly USNA-themed Annapolis home?

Checkout is at 11:00 AM.

Where is Parking & Pet Friendly USNA-themed Annapolis home located?

Located in the heart of Annapolis, this holiday home is within 1 mi (2 km) of People's Brewer Hill Cemetery and U.S. Naval Academy. Annapolis Civil Rights Plaque and Asbury United Methodist Church are also within 10 minutes.

Reviews

9.8

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 27 reviews
Rating 8 - Good. 3 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Kate R.

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

Great little place in the heart of Annapolis

We liked our stay at this house. It central to all kinds of great restaurants and walk-abouts in Annapolis.
Stayed 11 nights in Jul 2025

10/10 Excellent

Todd B.

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

Great stay!

Perfect location for our visit to USNA and super clean!
Stayed 4 nights in Feb 2022

10/10 Excellent

Alex C.

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

Great location, beautiful original charm. Would definitely stay again!

Could not have been better!
Stayed 2 nights in Mar 2021

10/10 Excellent

Steven S.

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

great location, great place

terrific location and wonderful property to included the outdoor spaces, which we used every day - many restaurants, shops, etc within walking distance - we could not have been more pleased -thank you!
Stayed 4 nights in Aug 2022

10/10 Excellent

Joseph R.

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

Great family home.

We had a great time, the home is walking distance to everything including the Naval Academy. Great restaurants very close by. Check in was very smooth as was communication with the owners.
Stayed 3 nights in Jun 2023

10/10 Excellent

Jerald B.

Liked: Cleanliness, communication, location, listing accuracy

Great visit with our Mid

Terrific location and home!
Stayed 2 nights in Apr 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Janet W.

Good location

We enjoyed our stay at the Midshipman den. It was clean, close to downtown and we were able to walk to the Navy football game.

10/10 Excellent

Melyssa H.

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

Great Stay

Great location! We felt well taken care of and our stay was seamless. Clean and comfortable. We enjoyed the outdoor gas fire pit and the added touch of a bottle of wine. Great stay!
Stayed 3 nights in Jun 2022

10/10 Excellent

John T.

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

Great stay in cute home!

Very lovely home and spacious for urbanites like us! Host was very gracious and communicative over email/text. Would def stay again!
Stayed 2 nights in Mar 2022

8/10 Good

Joanne W.

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

Great location for Navy football games!

Clean, cute and convenient!
Stayed 3 nights in Sep 2022

10/10 Excellent

Paul D.

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

40th Anniversary in Annapolis

Excellent location, safe and quiet. Well decorated and outfitted. Off street parking. Would gladly stay there again
Stayed 4 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Wonderful all around

This was the perfect house for our trip for parents weekend. It was close to the yard and also walking distance to a bunch of fun places to eat. The home was clean and well stocked with everything we needed to make our stay enjoyable. Will definitely be back!!
Stayed 3 nights in Aug 2022

8/10 Good

John K.

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

Great Property and Neighborhood

Accommodating owner.
Stayed 4 nights in Jun 2021

10/10 Excellent

Marcus R., North Potomac, MD USA

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

Relaxing respite

We enjoyed walking around downtown Annapolis and Eastport. Our stay was comfortable and relaxing. The kitchen was well equipped, and we enjoyed meals at the house, as well as some excellent restaurants within walking distance. We only used our car once during the week to secure provisions.
Stayed 9 nights in Aug 2023

10/10 Excellent

Mary M.

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

Great home-wonderful location!

Wonderful home and location in Annapolis within walking distance to the stadium! The home was very clean with everything you need for your home away from home. Close to places to eat. A bottle of wine and some chips greeted us on arrival which was a nice treat! Great communication from the booking to the end of our stay! Will definitely return!
Stayed 3 nights in Oct 2023

10/10 Excellent

David M.

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

Great Place! Great Location!

This place worked out perfect for us and the pup for Memorial Day Weekend! Great location! Just the right distance to experience everything on West Street all the way down to Main St and the docks. The outdoor space is great and everything was very clean. The house was equipped with everything you need, which a lot of the items appeared to be brand new. We will for sure consider this place again for our next trip to Annapolis!
Stayed 3 nights in May 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ted B.

Weekend Trip

We decided to take a last minute trip to Annapolis. The Midship Den is a perfect place for an Annapolis weekend. The house was clean and we really liked the location. Our Mid leaves for flight school in a week and he was able to spend his last weekend with us. We would recommend the Midship Den to anyone.

10/10 Excellent

Sandi R.

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

Great getaway

Stayed here for a last minute family getaway. The location was perfect. Very close to the heart of downtown. Very clean. Great backyard and fire pit. Well-stocked. Dog friendly with fenced yard and dog run right next door. The only caution is that the fence has a gap at bottom so a small or medium sized dog could crawl out.
Stayed 4 nights in Apr 2022
This review comes from a trusted partner site and has not been verified.

8/10 Good

Barbara R.

Boat Show Accommodation

This was a fair accommodation for three couples. Only one full bath made it a little challenging. The walk down to the docks for the boat show was a little far for those with back stress or those not in best of health. Cost was fair for boat show weekend.

10/10 Excellent

Emily V.

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

nice location in Annapolis - near stadium and several restaurants

We were in Annapolis for a football game, and appreciated being able to walk to/from the stadium. Great breakfast/lunch place less than a block away at Park Deli. Take out pizza from Carpaccio was very good and also less than a 5 minute walk. Short drive for donuts from Carlson's, and coffee from Ceremony coffee roasters. Can walk to downtown, the USNA, and lots of restaurants, I'd estimate about 15-20 minutes walk each way. House was very clean and had everything we needed for our short stay (eg paper towels, toilet paper, coffee, dishwashing detergent, soap). Simple check in/check out. We had a little trouble getting the heating just right, but likely user error. Overall we were very pleased, and would stay here again!
Stayed 3 nights in Dec 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Aaron

Close and Convenient w nice patio

It was nice to sit outside in the patio and look at the fire pit 🔥 while grilling 🥩 steaks and drinking a California 🍷
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Teresa

We rented the MidshipDen for Commissioning week and could not have had a better experience.

We rented the MidshipDen for Commissioning week and could not have had a better experience. The house was clean, nicely decorated and had all the amenities we needed including a fenced backyard and off-street parking. It is within walking distance of the Naval Academy, football stadium and DTA.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Brooke C.

Great house, awesome location

We couldn't have asked for a better place to stay for our visit to Annapolis! The MidshipDen is beautifully decorated and perfectly located in downtown Annapolis within walking distance to some of our favorite restaurants. We had all of the amenities we needed and we were very thankful for a pet-friendly house with a fenced in backyard so we could bring our 4-legged family member with us :) We will definitely be staying here again next time we're in Annapolis and I suggest you do, too!

10/10 Excellent

Danny G.

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

Great Location. Great Stay

The MidShip Den was very clean, well appointed, and in a great location for those looking to explore Annapolis. Sean was a great communicator from the booking process all the way through our stay. The beds and linens were very comfortable…often an overthought when booking a property. Restaurants/bars/coffee and small retail shops are just around the corner. It is just under a mile to downtown, which was a very nice walk we did daily, making many stops along the way. Some minor things to consider regarding the house… This is a multi-family house, so the entirety of the property is shared. Although there are some nice modern touches, it is definitely an older home. The 1.5 bathrooms do not have locks and the doors can be a bit creaky, so the house can occasionally be a bit loud when it’s quiet. This not something that bothered us, but possibly worth mentioning. The backyard and back porch are definitely on the smaller side. This was probably the only disappoint we experienced as we generally like to hang out in the backyard, eat, and have some drinks. There really is no space for more than 2 people to do that. Parking is also very tight as we had to squeeze into our side by side SUV’s. Not an issue for us, but again, worth mentioning. All in all we had a great stay and enjoyed what this house had to offer. Would certainly recommend this property to anyone looking the visit Annapolis. Thank you to Sean and iTrip.
Stayed 4 nights in Aug 2021

10/10 Excellent

Ellen M., Denver, USA

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

Easy access to cool activities

This home was conveniently located, easy to house a family, and functional. The property managers were super helpful.
Stayed 3 nights in Jun 2021

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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