Entire home

Chesapeake Comfort, Annapolis.

Holiday home with kitchen, near U.S. Naval Academy

Overview
Location
Amenities
Policies

Exceptional

3 bedrooms2 bathroomsSleeps 62000 sq ft

Popular amenities

Barbecue grill
Washer
Dryer
Kitchen

Explore the area

Annapolis, MD

Place, Navy-Marine Corps Memorial Stadium
‪5 min walk‬
Place, U.S. Naval Academy
‪16 min walk‬
Place, Annapolis City Dock
‪4 min drive‬
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
‪31 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Double Beds

2 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio

Kitchen

About this property

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.

Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Kitchen
Washer
Dryer
Pet-friendly

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 12:00 PM

Children

Children allowed: ages 13–17

Events

No events allowed

Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)

Smoking

Smoking is not permitted

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.

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

Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

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

Located in Annapolis, this holiday home is in the city centre. 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 French Soldiers Monument. 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 ecotours and hiking/biking trails nearby.

View more Holiday homes in Annapolis

Annapolis, MD

What's nearby

Navy-Marine Corps Memorial Stadium - 5 min walk - 0.4 km
Maryland Hall for Creative Arts - 16 min walk - 1.3 km
U.S. Naval Academy - 16 min walk - 1.4 km
Maryland State House - 17 min walk - 1.5 km
Annapolis City Dock - 4 min drive - 1.8 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
‪Miss Shirley's Cafe - ‬13 min walk
‪LeveL: a small plates lounge - ‬12 min walk
‪Curate - ‬13 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 23 kg per pet.

How much is parking at Chesapeake Comfort, Annapolis. ?

On-site 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. ?

Checkout is at 12:00 PM.

Where is Chesapeake Comfort, Annapolis. located?

Located in the heart of Annapolis, this holiday 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.

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Krista B.

16 Nov 2025

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

10/10 Excellent

Danielle M.

29 Jun 2025

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

10/10 Excellent

tom c.

19 Jun 2025

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

10/10 Excellent

Diane L.

13 Sept 2024

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

10/10 Excellent

Patricia C.

26 Dec 2022

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

10/10 Excellent

Kristine A., Lexington, MA USA

1 Apr 2023

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

10/10 Excellent

brooke a.

30 Jun 2025

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

6/10 Okay

janet s.

30 Sept 2025

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

Stayed 5 nights in Sep 2025

10/10 Excellent

Laura Z.

19 Jan 2023

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

10/10 Excellent

David H.

22 May 2023

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

10/10 Excellent

Danielle G.

29 Aug 2023

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

10/10 Excellent

Rob W.

25 Jun 2023

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

10/10 Excellent

Francine H.

28 Mar 2024

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

10/10 Excellent

Amy H.

27 Mar 2023

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

10/10 Excellent

Angie F.

16 Apr 2023

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

10/10 Excellent

Jackie A., Warrington PA, USA

3 Apr 2023

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

10/10 Excellent

Vincent S., Annapolis

26 Oct 2023

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

10/10 Excellent

Kathy S., Long Neck, DE

15 Jun 2023

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