Jackson's Bunker in Eastport with fenced-in backyard and dog friendly | House in Annapolis

9.4 (13 Reviews) |   Pet Friendly   3 Bedrooms  2 Bathrooms  12 Guests  Stay&Play
Hillsmere House | Jackson's Bunker in Eastport with fenced-in backyard and dog friendly

3 Bedroom House in Hillsmere, Annapolis

Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, the waterfront and Truxton Park. The 3 bedroom, 2 bath home has recently been renovated and has plenty of space and beds for 2 families traveling together or a large extended family. The first floor has a Queen bed, full bath and room for 2 more on the pullout sofa in the Family room. Head out to the beautiful fenced-in backyard with a deck to enjoy your (complimentary) morning coffee. There is a furnished covered living space out in the backyard to enjoy a glass of wine upon your arrival.
Head back in the house and up the stairs to the 2 bedrooms, den and full bath in the hall. The first guest room has a Queen bed, the second has a full and 2 twin beds and the den has a futon sofa that sleeps 1 adult comfortably or 2 small children.
There is free and unrestricted street parking in Eastport. A one mile walk, bike ride or drive will bring you to downtown Annapolis, where you’ll find Main Street shops, more restaurants, bars and the beautiful Ego Alley! This home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis.
SLEEPING ARRANGEMENTS 3 BR/2 BA / Sleeps 10 adults or 8 adults and 4 children/teens:
Main Floor En-Suite Queen Bedroom:
-Queen Bed
-Full Bath
Main Floor Family Room
-Queen sofa bed
-Desk and desk chair
-Full bath in the hall
Queen Guest room
-Queen bed
-2nd Floor
-Full bath in the hall
Upstairs Guest room
-Full Bed and 2 Twin beds
-Full bath in the hall
Upstairs Den
-Full Futon
-Full bath in the hall
HIGHLIGHTS:
-Full kitchen
-Dining tabletop seats 4
-Private fenced backyard
-Back deck and covered furnished living space
-BBQ grill (propane included)
-High Speed Internet and WiFi
-Big Screen Smart TV.
-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
-Un-restricted street parking
-Full-sized washer & dryer located inside the home
-No smoking
-Dogs Allowed with Non-refundable $150 deposit per pet.
-Keyless entry. Drive straight to your rental home and enter the front door with a lock code.
Property Distance to:
-Downtown Annapolis – 1.6 miles
-U.S. Naval Academy – 1.6 miles
-Washington, DC – 39 miles
-Baltimore - 31 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 made 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 pets unless the $150 non-refundable pet deposit has been paid prior to checkin. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. 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

Jackson's Bunker in Eastport with fenced-in backyard and dog friendly is located in Hillsmere. Jackson's Bunker in Eastport with fenced-in backyard and dog friendly provides accommodation, featuring Kitchen, Laundry, Parking, among other amenities. This House features Kitchen, Laundry, Parking, to make your stay a comfortable one.

Jackson's Bunker in Eastport with fenced-in backyard and dog friendly has 3 Bedrooms , 2 Bathrooms, and max occupancy of 12 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Hillsmere has interesting places to visit. If you want to learn more about the House in Hillsmere, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 11:00 am
Child Policy Children are welcome.
Pet Policy Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy Smoking is not permitted
Other Policy 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 host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip host has not indicated whether there is a smoke detector on the property onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Annapolis, 21403, USA

What Our Guests say 500 + Reviews

May 27, 2025 12:07:22 AM
Summary: My family enjoyed staying in this charming home for USNA's commissioning weekend. The location was a great jumping off point for activities at the Naval Academy, but kept us out of the heart of traffic and tourism. The home was very clean with a well appointed kitchen, a fantastically huge couch and a great big back yard that we didn't get to enjoy nearly enough because of the rain. The owners were very responsive to two minor issues and promptly provided service to fix them. I would highly recommend the Jackson Bunker as a comfortable and convenient home to enjoy during your Annapolis stay.
Elizabeth J. Elizabeth J.
Sep 16, 2024 02:55:43 AM
Summary: We were just minutes away from all the good restaurants, shops, sights, and harbor. Safe area. Place as described, but no nightstands by any of the beds. One room had a closet and no drawers, the other drawers and no closets. Manager responded immediately to any questions. Great customer service. We would stay there again.
Jane F. Jane F.
Jul 24, 2024 09:23:58 AM
Summary: We had a great weekend at Jackson’s Bunker - perfect for our family of 4 (and definitely room for more) The property was super easy to check into, clean and great location. Our dog loved the fenced in yard, as did our young kids. Host provided a guidebook with all information in one spot. We can see ourselves returning!
Laura V. Laura V.
Mar 16, 2024 03:54:39 AM
Summary: This home has a fenced-in backyard and is dog-friendly, making it a good spot for visiting Annapolis with a dog in tow. Along with being a five-minute drive to downtown Annapolis, this home is also close to Quiet Waters Park. Sean is terrific at communicating; the complimentary wine and coffee were appreciated!
Lynn H. Lynn H.
Nov 21, 2023 10:10:59 PM
Summary: Jackson’s bunker was the perfect place to spend the weekend with our plebe. There’s plenty of space to spread out and relax. Even though it was chilly, we still enjoyed using the sitting area in the backyard. Easy walk to restaurants and Walgreens.
AnneMarie V. AnneMarie V.
Oct 14, 2023 05:52:16 AM
Summary: A great home base for the weekend! An easy 1.4 mile walk to downtown Annapolis. Huge sectional in the living room to be the center of great conversation and games. We stayed for a long weekend and had a great time at Jackson’s Bunker.
Timothy G. Timothy G.
Sep 1, 2023 08:37:16 AM
Summary: Our stay was wonderful and cozy, property was exactly as described. We enjoyed our stay and it is conveniently located near all the things in Annapolis. Would recommend to anyone visiting the area.
Janelleen Janelleen
Aug 15, 2023 12:00:27 PM
Summary: Son goes to UMD and decided to plan short trip with friends to Annapolis! Cute house, very clean and has everything you need if you are in and out exploring the sites! Walking distance to Bakery and fantastic brewery and not long to downtown! Perfect for 2 families if you are flexible with sleeping arrangements! Room with 3 beds perfect for our college boys!
Jennifer S. Jennifer S.
Nov 11, 2022 11:02:04 PM
Summary: Overall we had a very great stay at Hillsmere. The house was cleaned and very well stocked for any number of guest to stay. the complimentary bottle of wine is always a nice touch. The backyard was very open, inviting and cozy to sit and relax with friends. There was a small hiccup upon check-in when the door lock stopped working. The customer service provided was quick and easy. Overall we had a great short stay here with Sean.
Craig M. Craig M.
Sep 27, 2022 06:39:22 AM
Summary: This home is so cozy and perfect for any family or gathering! They have taken an old house and turned it into a cute and well furnished home away from home. Only 1.3 miles away from downtown. Easy to find, well maintained, and great amenities. Definitely would recommend for your stay in Annapolis
Hannah F. Hannah F.

FAQ's

Is this Hillsmere house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Hillsmere house have a swimming pool?

No, this Hillsmere house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Hillsmere house?

Best-rates for the Hillsmere house starts from $506 per night with includes Bedding/Linens, Wellness Facilities, Barbecue/Outdoor Cooking, Child Friendly, Air Conditioner, Balcony/Terrace, Fireplace/Heating, Internet, Kitchen, Laundry, Parking, Pet Friendly, TV, Security/Safety StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Hillsmere house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Hillsmere house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Hillsmere house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Hillsmere house?

Based on the information reported by the owner or manager, the Hillsmere house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Hillsmere house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Hillsmere house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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