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Chesapeake Comfort, Annapolis.

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Step into the Annapolis Bungalow Home, a charming retreat professionally cleaned and designed for comfort. Take a stroll to Navy Stadium or hop on the trolley at Park Place and explore downtown. Enjoy relaxing evenings on the spacious backyard deck, or launch your kayak from nearby waters.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6186 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Chesapeake Comfort, Annapolis.

Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost with other listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town.There is a kayak/paddle launch at the bottom of the street. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. No recording devices are inside the home, strictly outside and in sight so that we can monitor who is coming inside the home as per VRBO policy. One doorbell camera and one backyard camera.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina

Things to do

  • Basketball nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Ice skating nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Scuba diving nearby
  • Swimming nearby
  • Winery tours nearby

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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 2,000 square feet

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Historic Inns of Annapolis
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  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, Wonderful, 1,851 reviews
The price is AED 428
AED 614 total
includes taxes & fees
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 12:00 PM
Contactless check-out available

Special check-in instructions

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

Rules

Please be considerate of our wonderful neighbors and respect our quiet hours after 11pm.
Do your best to remove your shoes inside. We try to keep our home as clean as possible at all times. Not a must, just do your best.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)

Children and extra beds

Children are welcome

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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

About the neighborhood

Located in Annapolis, this vacation home is in the city center. Annapolis Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and some of the area's attractions include Helen Avalynne Tawes Garden and Maryland Hall for Creative Arts. Looking to enjoy an event or a game while in town? See what's happening at Navy-Marine Corps Memorial Stadium or Alumni Hall. Kayaking and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby. Visit our Annapolis travel guide
View more Vacation Homes in Annapolis
Map
Annapolis, MD

What's nearby

  • Maryland State House
    Maryland State House
    19 min walk - 1.6 km
  • U.S. Naval Academy
    U.S. Naval Academy
    4 min drive - 2.8 km
  • William Paca House
    William Paca House
    5 min drive - 3.2 km
  • Navy-Marine Corps Memorial Stadium
    8 min walk - 0.7 km
  • Annapolis City Dock
    5 min drive - 3.2 km

Getting around

  • Odenton Station
    20 min drive
  • Fort Meade, MD (FME-Tipton)
    25 min drive

Restaurants

  • Graul's Market
    13 min walk
  • Rams Head Tavern
    13 min walk
  • Leo
    14 min walk
  • LeveL: a small plates lounge
    12 min walk
  • Lemongrass
    14 min walk

Frequently asked questions

Is Chesapeake Comfort, Annapolis. pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Chesapeake Comfort, Annapolis. ?

Check-in begins at 4:00 PM.

What time is check-out at Chesapeake Comfort, Annapolis. ?

Check-out is at 12:00 PM.

Where is Chesapeake Comfort, Annapolis. located?

Located in the heart of Annapolis, this vacation home is within a 10-minute walk of Peters Cove, Navy-Marine Corps Memorial Stadium, and Helen Avalynne Tawes Garden. Stanton School & Community Center and First Baptist Church are also within 10 minutes.

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Chesapeake Comfort, Annapolis. Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 18 out of 20 reviews
Rating 8 - Good. 1 out of 20 reviews
Rating 6 - Okay. 1 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10

Cleanliness

9.6

Location

Reviews

Verified

10/10 Excellent

Vincent S.

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

Excellent Location in Annapolis

The home was exactly as listed and perfect for my wife and I and her father and his wife. The home was clean and had everything we needed. We also brought our miniature golden doodle and she enjoyed the enclosed back yard. The host was responsive to the few questions we had. We lived in Annapolis for 8 years and recently moved back to the Northeast. This location is perfect for downtown Annapolis and many other attractions. With DC a short ride, we visited the Army Museum and Arlington National Cemetery. I would recommend this home for anyone looking to stay in Annapolis or visiting DC.
Stayed 4 nights in Oct 2023
Verified

10/10 Excellent

Stephanie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, nice space, great backyard to hang out with dogs.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Krista B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was clean and was a great location so close to the stadium.
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Danielle M.

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

Weekend grad celebration

Great place centrally located to amenities and Navy stadium. We booked an overnite with family to attend a graduation dinner nearby.
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Patricia C.

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

Christmas Weekend Getaway

Charming bungalow with very comfortable furnishings! We enjoyed our stay very much and look forward to staying again sometime in the near future.
Stayed 2 nights in Dec 2022
Verified

10/10 Excellent

Diane L.

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

Great location and comfortable home

Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive.
Stayed 1 night in Sep 2024
Verified

10/10 Excellent

Kristine A.

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

Annapolis Home

I was there for 2 nights- great neighborhood, beautiful home and great host! Backyard great for my dogs. Would be happy to stay there again.
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

tom c.

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

Convenient

Very nice house. Quiet and clean. Very convenient to stadium
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Laura Z.

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

Comfortable! Good stay

Very nice classic bungalow house that's been remodeled to maximize comfort and use of space. Good furniture, good kitchen equipment, nice quality towels & bedding. Everything worked great and we enjoyed our stay. We appreciate that our dog was welcome.
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

David H.

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

Great neighborhood with access to amenities

Quiet street with lots of parking. Quick access to all around Annapolis and walkable for the young and young at heart. Had everything you need to have a quiet get together with friends. Great backyard and outdoor area. We'll definitely be staying again.
Stayed 5 nights in May 2023
Verified

10/10 Excellent

Danielle G.

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

Annapolis weekend

The house was as expected and Collin was very responsive. No complaints!
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Rob W.

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

Nice Annapolis getaway

We stayed for the weekend to visit our Mid. Nice house. Clean and well appointed. More spacious than you’d expect, particularly the basement. It would be a great place for a football weekend.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

brooke a.

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

Plebe weekend stay

The house was perfect for our family. The family room couch was perfect for us to all snuggle up together and watch TV or just relax. Plenty of room in the house for everybody to spread out as well.We had a small issue with the alarm pad beeping but Colin responded to my message promptly and was at the house to fix the problem in no time. Great house. Wonderful location if going to the Naval Academy.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Francine H.

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

Cozy and convenient home

My husband and I stayed here with another couple and we really enjoyed our visit. We had everything we needed. Colin was very helpful and accessible. He even stopped by to show us how to use the Apple remote for the television. I highly recommend this property!
Stayed 3 nights in Mar 2024
Verified

10/10 Excellent

Amy H.

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

Perfect Property!

Collin was a fabulous host! Everything was even better than what we expected according to the listing. We were in Annapolis for a girls weekend….We had a wonderful time, the amenities were above and beyond what we’ve come accustomed to with other VRBO properties. Communication with Colin was exceptional. We loved our stay and will definitely choose this property again if we return to Annapolis!
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

Angie F.

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

This house was great!

Great house. Very clean and comfortable. Much bigger than it appears from outside. 3 bedrooms that are all on separate floor. Great privacy for the 3 couples that we had there. Back yard is awesome with lots of room, lights etc and fenced in for dogs. We easily walked to and from the Navy stadium for lacrosse game. We would Definately rent again.
Stayed 2 nights in Apr 2023
Verified

6/10 Okay

janet s.

Liked: Cleanliness, check-in, communication
The house was nice good WiFi, the TV needed to have some instructions as it was different to a lot of other Vrbo ones we have used, location to the stadium excellent for people going to the games, road very busy during the day as school close, verging on a not very good neighborhood. We had no problems. I did comment to the realtor/manager that the back yard was a mess, with junk that needed tidying up and plants and grass needed tending to, plus the mosquitoes were horrendous
Junk laying around
Needed work
Broken table
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Jackie A.

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

Nice house in a good neighborhood

We stayed 2 nights. The house is nice, clean and comfortable. The driveway can hold 3 cars. The owner was very responsive and helpful when the VRBO App didn't work at check-in. It's in a quiet neighborhood, which is up the hill from the parking garage and the free shuttle, making it easy to access downtown. We didn't use the backyard due to the weather.
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

Kathy S.

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

Nice Weekend Getaway

Property was great for our stay. Some of us are loud sleelers so the bedroom on each level helped. There was a lot going on in the area during our stay so it was difficult to get around with all the traffic. However, if you are looking to stay close to the stadium this place is walking distance! The amenities here were terrific, down to providing coffee, filters, sugar, etc. The backyard is fenced in,l with a firepit and firewood....which unfortunately we didnt have a chance to use. The only trouble we had was using the Apple TV, but that was because none of us ever used it before, lol.
Stayed 2 nights in Jun 2023
Verified

8/10 Good

Vinton V.

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

Annapolis

Everything was wonderful, inside and outside spaces great, the home management tablet reminded us one of the systems was offline.
Stayed 2 nights in May 2025