Title: Chesapeake Comfort, Annapolis. - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Chesapeake Comfort, Annapolis. Vacation home with kitchen, near U.S. Naval Academy ## Photo gallery for Chesapeake Comfort, Annapolis. ![Terrace/patio - Chesapeake Comfort, Annapolis. (Annapolis)](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/w1170h769x0y5-a7eb7ccc.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV, books - Chesapeake Comfort, Annapolis. (Annapolis)](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/bd0aa05c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Chesapeake Comfort, Annapolis. (Annapolis)](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/w1170h778x0y0-0d9b0ad4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, books - Chesapeake Comfort, Annapolis. (Annapolis)](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/3f7a0147.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, books - Chesapeake Comfort, Annapolis. (Annapolis)](https://images.trvl-media.com/lodging/58000000/57360000/57359100/57359083/a0026e1b.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 62000 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## 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 ## Similar properties ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33510000/33507700/33507691/27fb4dc0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### New Waterfront Home near Annapolis, MD Harwood - Pool - Kitchen - Washer - Dryer 10 Exceptional 33 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=33507691&PinnedHotelID=33507691&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/58000000/57120000/57118800/57118800/64d1dfa9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Scenic Waterfront Getaway with Private Pool and Pier, Minutes from Annapolis Cape St. John - Pool - Kitchen - Washer - Dryer 10 Exceptional 115 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=57118800&PinnedHotelID=57118800&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/79000000/78290000/78289700/78289655/cab51684.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic Downtown Annapolis Gem Steps to USNA and Main St with Private Patio and Parking Historic District - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 25 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=78289655&PinnedHotelID=78289655&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, books](https://images.trvl-media.com/lodging/114000000/113580000/113578900/113578868/f0ffb1fd.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful Historic Flat next to City Dock + USNA Historic District - Kitchen - Washer - Free WiFi - Air conditioning 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=113578868&PinnedHotelID=113578868&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111200000/111193300/111193202/8d123a9a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Newly renovated in DTA w parking Murray Hill - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 10 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=111193202&PinnedHotelID=111193202&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/67000000/66850000/66845500/66845427/4cc6cb4b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 421 Irie: Simply Charming 2 Story COTTAGE!! 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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 ### Property is also known as Vrbo Property Bouvet Island Vrbo Property Private vacation home Vrbo Property Private vacation home Bouvet Island ## About the area Located in Annapolis, this vacation home is in the city center. Annapolis Civil Rights Plaque and Banneker Douglass Museum 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 cycling and ecotours nearby. [Visit our Annapolis travel guide](https://www.expedia.ca/Annapolis.dx6034082) [View more Vacation homes in Annapolis](https://www.expedia.ca/Annapolis-Private-Vacation-Homes.d6034082-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C38.98097%2C-76.50400&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=obwP8-NFKvocl7-EjN7gTmWaVE8=) Annapolis, MD ### What's nearby - ![U.S. Naval Academy featuring military items, interior views and heritage architecture](https://images.trvl-media.com/place/6077390/365a14c8-731b-4cc4-a5d7-9baf0c5edd8f.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) U.S. Naval Academy 16 min walk \- 1.4 km - ![Maryland State House featuring heritage elements and interior views](https://images.trvl-media.com/place/6077394/efd8bda7-e742-4ff4-a0c4-f5be726abcf9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Maryland State House 17 min walk \- 1.5 km - Navy-Marine Corps Memorial Stadium 5 min walk \- 0.4 km - Maryland Hall for Creative Arts 16 min walk \- 1.3 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 - LeveL: a small plates lounge 12 min walk - Miss Shirley's Cafe 13 min walk - Kitchen on West St 15 min walk ## Frequently asked questions ### Is Chesapeake Comfort, Annapolis. pet-friendly? ### How much is parking? ### What time is check-in at Chesapeake Comfort, Annapolis. ? ### What time is check-out at Chesapeake Comfort, Annapolis. ? ### Where is Chesapeake Comfort, Annapolis. located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Chesapeake Comfort, Annapolis. Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers 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. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 18 8 - Good 1 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 9.6 Location ## Reviews ### 10/10 Excellent #### Vincent S., Annapolis Oct 26, 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. ##### Vincent S. Stayed 4 nights in Oct 2023 ### 10/10 Excellent #### Danielle M. Jun 29, 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. ##### Danielle M. Stayed 1 night in Jun 2025 ### 10/10 Excellent #### tom c. Jun 19, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Convenient Very nice house. Quiet and clean. Very convenient to stadium ##### tom c. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Patricia C. Dec 26, 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. ##### Patricia C. Stayed 2 nights in Dec 2022 ### 10/10 Excellent #### Diane L. Sep 13, 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. ##### Diane L. Stayed 1 night in Sep 2024 ### 10/10 Excellent #### Kristine A., Lexington, MA USA Apr 1, 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. ##### Kristine A. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### brooke a. Jun 30, 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. ##### brooke a. Stayed 4 nights in Jun 2025 ### 10/10 Excellent #### Laura Z. Jan 19, 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. ##### Laura Z. Stayed 2 nights in Jan 2023 ### 10/10 Excellent #### David H. May 22, 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. ##### David H. Stayed 5 nights in May 2023 ### 10/10 Excellent #### Danielle G. Aug 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Annapolis weekend The house was as expected and Collin was very responsive. No complaints! ##### Danielle G. Stayed 2 nights in Aug 2023 ### 10/10 Excellent #### Rob W. Jun 25, 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. ##### Rob W. Stayed 2 nights in Jun 2023 ### 10/10 Excellent #### Francine H. Mar 28, 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! ##### Francine H. Stayed 3 nights in Mar 2024 ### 6/10 Okay #### janet s. Sep 30, 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 ![Junk laying around](https://a.travel-assets.com/ugc/hotel-reviews/ee9f746b-284f-419f-b858-1587189b09ff-1759265486764.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![Needed work](https://a.travel-assets.com/ugc/hotel-reviews/17ddf57b-5ae7-42b6-9ae0-19d13ea10df5-1759265486980.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![Broken table](https://a.travel-assets.com/ugc/hotel-reviews/70dcdfba-f8b5-471d-9caa-c71e7dc09f9a-1759265483344.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### janet s. Stayed 5 nights in Sep 2025 ### 10/10 Excellent #### Amy H. Mar 27, 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! ##### Amy H. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Angie F. Apr 16, 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. ##### Angie F. Stayed 2 nights in Apr 2023 ### 10/10 Excellent #### Jackie A., Warrington PA, USA Apr 3, 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. ##### Jackie A. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Kathy S., Long Neck, DE Jun 15, 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. ##### Kathy S. Stayed 2 nights in Jun 2023 ### 8/10 Good #### Vinton V. May 9, 2025 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. ##### Vinton V. 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