2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
Experience the Difference: Professionally Managed by iTrip Annapolis
Escape to this spectacular custom-built waterfront estate in Edgewater, MD—just 15 minutes from downtown Annapolis. Styled like a modern ski chalet and nestled on nearly 2 private acres with a private pier and beach access, this one-of-a-kind retreat offers sweeping views of the South River, expansive indoor and outdoor living spaces, and every amenity for your perfect stay.
The Space
Step inside to a stunning open floor plan with soaring ceilings and panoramic water views. Gather in the main living area with its 2-story windows, cozy gas fireplace, and two flatscreen TVs. The gourmet kitchen is a chef’s dream, featuring a double oven, two cooktops (including one in the oversized butler’s pantry), a warming drawer, double refrigerator, wine cooler, and ice maker.
For more casual fun, head to the spacious lower level—perfect for kids and teens—with a giant sectional, game and ping-pong tables, flatscreen TV, work desk, and a full bath.
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Edgewater
Located in Edgewater, this holiday home is on the beach. The area's natural beauty can be seen at Chesapeake Bay and Smithsonian Environmental Research Center, while London Town and Ballet Theater of Maryland are cultural highlights. Wild Bird Center and Annapolis Bowl are also worth visiting.
Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
As of 13 May, 2026, prices found for a 1-night stay for 2 adults at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free on 5 Jul, 2026 start from S$2,231, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
On-site parking is available at the property.
What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Check-in begins at 4:00 PM.
What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Checkout is at 11:00 AM.
Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free located?
Nestled on the beach, this Edgewater holiday home is steps from London Town and 2.9 mi (4.7 km) from South River Golf Links. Smithsonian Environmental Research Center and Annapolis Harbour Center are also within 6 miles (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Did not use hot tub. Many nicely distributed spaces for three families Christmas gathering appreciated large dining table
Margaret J.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 30 Dec, 2025
Thanks, Margaret! We’re thrilled that On The Waterfront offered the perfect setting for your Christmas gathering with three families. It's wonderful to hear that the multiple spaces and the large dining table met your needs. We hope to welcome you back for another memorable stay in the future! Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Nora B.
25 May, 2025
Perfect location, beautiful and spacious home!
We could not have asked for a better place to stay for commissioning week! The views were amazing! The house was beautiful, had everything we needed! Itrips was so helpful, couldn’t ask for a better rental management company. House was super clean, beds were comfortable!
Nora B.
Response from VrboOwner on 28 May, 2025
Hi Nora! Thank you for being a great guest & we welcome you back anytime! We're thrilled to hear that On The Waterfront was perfect for your stay during the 2025 Commissioning week. We look forward to hosting you again on your next trip! Melissa~iTripAnnapolis
We were a family group of 10 adults and 2 teens. The house was big enough for all with high ceilings, many en-suites, a hot tub and a pier. Hosts were only a text away.
Marc S.
Stayed 3 nights in Jun 2025
Response from VrboOwner on 4 Jul, 2025
Thanks, Marc! We're thrilled to hear that On The Waterfront was spacious enough for your family group and that you enjoyed the high ceilings, en-suites, hot tub, and pier. It's great to know that our team was readily available to assist you. We hope to welcome you back for another memorable stay in the future! Melissa~iTrip Annapolis
Our group could not say enough good things about this house! Every room had a bathroom and it was very comfortable for a big group. Hot tub and dock were so nice. Many of our friends said they’d rent the house again for a different trip!
Caitlin C.
Stayed 3 nights in Jul 2024
Response from VrboOwner on 30 Jul, 2024
Hi Caitlin! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
We had a great time. The property was just as described. Very big, clean and comfortable. We are definitely going to come back. Any communication we had was pleasant with the management. Thank you for a wonderful experience.
David F.
Stayed 4 nights in May 2023
Response from VrboOwner on 14 Jun, 2023
Thank you so much for your review of On The Waterfront. Please come back and stay with us again. Safe Travels!
-Tiffany
The pictures didn't do it justice. The space is HUGE! It was also exceptionally clean. Honestly, it could not have been better. I would recommend this house to anyone.
Jenny S.
Stayed 3 nights in Sep 2023
Response from VrboOwner on 4 Oct, 2023
Thank you Jenny for the kind review of On the Waterfront. Please come back and stay with us again. Safe Travels!
-Tiffany
This is a comfortable, very well appointed home. We were inspired and delighted by the beautiful view of the South River. Osprey flew about, boats passed by, we could just sit on the deck and enjoy it. A nice feature was that there were large tables for inside and outside dining for our party of ten. We were pleased that there were three bedrooms on the main level which is hard to find. We enjoyed out stay.
Margaret J.
Stayed 4 nights in May 2024
Response from VrboOwner on 11 Jun, 2024
Hi Margaret- thank you for allowing us to host the stay & we welcome you back anytime! Melissa~iTripAnnapolis
We were really impressed with both the layout of the house and the amenities it offered. The nursery attached to the upstairs bedroom gave our grandson some much needed rest. The kitchen was well equipped. The hot tub was clean and refreshing. Thanks to the owners for sharing.
Neal H.
Stayed 3 nights in Sep 2023
Response from VrboOwner on 24 Oct, 2023
Thanks, Neal! We look forward to hosting you again any time.
Sean
A group of 11 stayed at this beautiful property for a team building and continuing education weekend. Even though the weather was rainy, we thoroughly enjoyed the gorgeous home and property. Comfortable beds and beautiful finishes. We did have 4 adults who slept in the bunk beds, so as long as you are agile it works. I also highly recommend local private chef, Zachary Pope. He created an amazing dinner for our group one evening.
Meghan J.
Stayed 4 nights in May 2024
Response from VrboOwner on 13 May, 2024
Hi Meghan! Thank you for sharing your wonderful stay experience in such a positive review! We would be happy to host you again, Melissa~iTripAnnapolis
My family of 14 adults found the house to be beautiful, clean and spacious during our 6 days stay. The beds were very comfortable and having 2 kitchens was a bonus. We did encounter a few drawbacks, however. The master bathtub leaked water onto the bathroom floor after running the spigot for less than a minute. While the property manager was quick to respond and offered to send an engineer the next morning, we did not wish for the interruption of what the repair time might take. In addition, the water from the faucets tasted differently than what we are used to, so we ended up purchasing bottled water for our entire stay. On the last night of our stay, we heard a loud clamoring noise off and on throughout the night that kept many of us up. Moreover, I was initially informed that we would only receive one roll of toilet paper per each of the 7 bathrooms and that we needed to supply our own after that. When I noted that we are 14 people staying for 6 days, the response was 2 rolls per bathroom after which we would have to supply our own. We did not like having to negotiate the number of rolls of toilet paper and being required to supply our own after a certain limit.
Jean O.
Stayed 5 nights in Dec 2025
Response from VrboOwner on 29 Jan, 2026
I’m sorry you did not find everything to be absolutely perfect like our guests have come to expect. Starter packs of two rolls of TP per bathroom are fairly standard, and we do post that ahead of time in several areas. But so glad you enjoyed the home otherwise, and we welcome you back again any time.
iTrip Annapolis
The house is gorgeous, everything was very comfortable and spacious. The hot tub was well maintained and very enjoyable. We greatly enjoyed the views, although there is no way to block the sunrise in the bedroom with the large windows. The outdoor property (yard) as explained in the arrival guide is a little more narrow than the photos show, but still a lovely space for lawn games, although we really didn't get to enjoy as much of the outdoors due to the rain.
The house is close to many restaurants and sights. Black Market Bakers and Always Ice Cream were winners that are only a mile away, and historic London Town Gardens is right around the corner. Overall, our stay was very nice.
The property guide does mention you may see the owner at the property, but we were not expecting him to request access to the property's basement inside the house on Easter morning. It wasn't a big deal, just a little awkward.
We also had an unfortunate incident on the morning of our departure when a tree fell in the driveway and partially on one of our vehicles. The property manager was responsive and helpful in getting someone there quickly to help start clearing a way out. However, the owner was reluctant in sharing any insurance information for his LLC that covers the property and only offered a small credit on a future stay. All the back and forth just made an already stressful situation more exhausting.
Erica J.
Stayed 4 nights in Mar 2024
Response from VrboOwner on 8 Apr, 2024
Erica,
Thanks for the feedback. The owner’s insurance info was provided by us within an hour. The owner’s initial offer to you was to extend your stay by a day at no charge. Understandably, you could not extend your trip, so that’s when we offered a credit toward a future stay. Sorry that wasn’t viewed as sufficient or fair on your part. This was an act of God and unfortunate, but we did not intend to add to your stress. In any case, we’re glad you enjoyed the home and we hope you’ll come back again in the future.
Sean, iTrip Annapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests