It doesn't get any better than this...to watch the sunsets from the front porch! One of few beachfront homes in Cape Charles!
Please SEE: Other Things to Note
For Area Details, Please SEE: The Neighborhood & Getting Around
*Pet Friendly, fee applies per pet.
The Space:
Down by the Bay, Home Features:
• 5 Bedroom, 4 Bath - Available for up to 12 Guests!
• Unbeatable Views of Chesapeake Bay
• Cross the Street to the Beach
• Free WiFi & Smart TVs
This large beachfront home has unbeatable views of the Chesapeake Bay and sleeps up to 12 people. This is a brand new vacation rental and one of few on the beach front in Cape Charles. This property has 4 full bathrooms (1 on each floor and 2 on the second floor) and 5 bedrooms (4 on the second floor and 1 on the 3rd floor).
Grab a towel & cross the street to the beach! This property has private parking behind the house and is great for families.
Guest Access:
We offer convenient door codes for self-check-in. Chesapeake Properties by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.
• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 4 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.
The Neighborhood:
Noted on the National Register of Historic Places, Northampton County's Cape Charles offers one of the largest concentrations of turn-of-the-century buildings on the East Coast. The historic district and small-town atmosphere create a serene and inviting community. Enjoy the history and experience galleries, boutiques, bookshops, and beautiful beach! Cape Charles Town Beach is the only free public beach on the Easter Shore of Virginia.
Things to See:
• Local Experiences: Take a Boat Tour, Kiteboarding, Kayaking, Paddleboarding, Explore the Beach, Fishing, Golf, Hiking, Biking, Birding & More!
- Shops: The Boardwalk, Table and Tonic Cape Charles, Cape Charles Candy Company, Love Letters, Gull Hummock Gourmet Market, Chessie's Toys and Games & more!
Annual Festivals & Events:
• Crabby Blues Festival
• Annual Crab Slam
• LOVEFest
• Sounds of the Shore
• Festive Fridays, Cape Charles Winter Wonderland (Nov-Dec)
• Free Concert in the Park (Summer Season)
• Grand Illumination (Dec)
We provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!
Getting Around:
Cape Charles is located near the southern tip of Virginia’s Eastern Shore right on the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. On the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow. The picturesque town of Cape Charles is filled with Americana, all about family and beautiful surroundings, voted one of the Happiest Seaside Towns by Coastal Living. Let the beach be your playground! Check out the walkable retail district, schedule a tee time at one of Bay Creek's award-winning golf courses, or take a water adventure for fishing and cruising.
Traveling to/around Cape Charles, Virginia:
• Golf Carts [Rentals: Eastern Shore Custom Carts and CC Ryder]
• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Wave Ryders]
• STAR Transit, local fixed route and bus service
• Bike/Cycling [Rentals: Poseidon Watersports, Trek Bicycle Virginia Beach, Rent Beach Buggies]
Airports:
• Norfolk International Airport (about 45 min by vehicle)
• Newport News Williamsburg International Airport (PHF)
• Accomack County Airport (MFV)
• Norfolk Ns (Chambers Fld) Airport (NGU)
• Langley Air Force Base (LFI)
Popular Landmarks:
• Cape Charles Museum and Welcome Center
• Kiptopeke State Park
• Cape Charles Natural Area Preserve
• Cape Charles Lighthouse
• Cape Charles Town Beach
• Cape Charles Brewing Company
Other Things to Note:
Please pay close attention to following the house rules. Non compliance could result in sizable fines.
- All guests staying at an Chesapeake Properties Vacation Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration.
- Age restrictions apply. Reservation holder must be 25 years of age.
- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Chesapeake Properties by Portoro directly.
- Known damages incurred during your stay must be reported to the property manager immediately.
- Before check in, we will send you detailed directions to ensure a seamless arrival.
- Check-in time is 4:00 p.m. Check-out time is 10:00 a.m.
- We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.
- Some homes have cameras for external monitoring only.
- HOTEL TAX COLLECTION: In the State of Virginia and in Northampton County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction.
- Some homes offer pools/hot tubs, or access to communal pools. There is no guard around the water features when available. Use at your own risk.
- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.
- Animals/Pets -- Dogs Only, Guidelines and Fee*
Animals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property.
-- The property allows for a maximum of 2 dogs at $150.00 per dog per stay.
For the safety of guests and the home, there are noise monitoring devices. These devices only measure the decibel level and do NOT record any audio.
Interaction with Guests:
Our goal is that your vacation exceed your expectations. Chesapeake Properties by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
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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
About the area
Cape Charles
Located in Historic Downtown Cape Charles, a neighbourhood in Cape Charles, this holiday home is in a rural area and on the beach. The area's natural beauty can be seen at Chesapeake Bay and Cape Charles Beach. Make sure you don't miss outdoor adventures like cycling and horse riding.
Cape Charles Museum & Welcome Center - 16 min walk - 1.4 km
Oyster Farm Marina - 18 min walk - 1.6 km
Kiptopeke State Park - 16 min drive - 20.8 km
Getting around
Norfolk, VA (ORF-Norfolk Intl.) - 50 min drive
Restaurants
Small’s Smokehouse - 5 min drive
Hardee's - 6 min drive
McDonald's - 5 min drive
Top China - 5 min drive
Sting-Ray's Restaurant - 10 min drive
Frequently asked questions
Is Down by the Bay - Chesapeake Properties pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Down by the Bay - Chesapeake Properties?
As of 13 May 2026, prices found for a 1-night stay for 2 adults at Down by the Bay - Chesapeake Properties on 7 October 2026 start from NZ$1,348, 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 Down by the Bay - Chesapeake Properties?
On-site parking is available at the property.
What time is check-in at Down by the Bay - Chesapeake Properties?
Check-in begins at 4:00 PM.
What time is check-out at Down by the Bay - Chesapeake Properties?
Checkout is at 10:00 AM.
Where is Down by the Bay - Chesapeake Properties located?
Located in Historic Downtown Cape Charles, this beachfront holiday home is in the city centre, just steps away from Chesapeake Bay and Cape Charles Beach. Cape Charles Harbor and Central Park are also within 10 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We loved the renovated kitchen and bathrooms and it was fantastic to be just across the street from the beach. Every night we were able to enjoy a beautiful sunset. The house had a lot of charm and it was a pleasure to be a guest there. Thank you!
Mindy W.
Stayed 5 nights in Oct 2025
Response from VrboOwner on 1 November 2025
Thank you for the review. We’re glad you enjoyed the renovated kitchen and bathrooms and loved being just across the street from the beach—those nightly sunsets are special. It was a pleasure to host you, and we’d welcome the chance to have you back.
This is our second year staying at Down By the Bay. Great location close to the beach, shops and restaurants. The house has everything you need for a family vacation. My favorite is the large kitchen with lots of storage space. Another wonderful vacation!
Robin W.
Stayed 5 nights in May 2025
Response from VrboOwner on 4 June 2025
Thank you for returning to Down By the Bay, Robin! We’re glad to hear you enjoyed the location and the amenities, especially the spacious kitchen. It’s great to know that you had another wonderful vacation with us. We look forward to welcoming you back for a third stay!
The house was roomy and comfortable for our family gathering. The location is very convenient, just a short walk from the beach. The house was clean, nicely decorated, and well equipped. Managers were responsive when asked about an item possibly needing repair.
Janice D.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 16 August 2025
Thank you! We’re so glad the house worked out perfectly for your family gathering and that you enjoyed the convenient location. We’re always happy to help with anything that comes up and would love to host you again!
Great location, plenty of room & well equipped! We had our 3 adult kids & spouses, 4 grands for the week & a few friends for a couple of days. Everyone had a blast and all agreed there is no need to go back to OBX. Great shops, food & drinks all within walking distance!
The Down by the Bay property is a wonderful house and a great location! It is an easy walk to the shops and restaurant around the corner and across the street to the beach. The kitchen is more spacious than other kitchens in Cape Charles vacation houses and there was ample space to store food and pantry items for a week. A big shout out to Chesapeake Properties for resolving a 2nd floor A/C issue in record time! Hope to return next year, same weekend!
It was not clean or well maintained. Not a great place for young children. Too many breakable nic nacs that we had to put away. Bed broke, third floor outlet had moisture coming out of it.
Randy T.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 5 July 2025
Thank you for sharing your experience. We're sorry to hear about the cleanliness and maintenance issues you faced, as well as the concerns with safety and comfort. We've addressed these points with our team to improve the space and ensure a safer environment. Your feedback is important to us.
From a partner site
10/10 Excellent
April W.
29 September 2023
Wonderful Long Weekend
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We loved coming to Cape Charles in September with our grown kids and grandchildren. The grandkids loved the third floor sleeping area. The kitchen living area were perfect to relax in. Being a block away from the main street and across the street from the beach were icing on the cake. everything was clean and well cared for. thank you
April W.
Stayed 4 nights in Sep 2023
From a partner site
10/10 Excellent
Kimberly M.
4 September 2023
Loved our vacation here!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
House was clean, spacious and very comfortable! The location was absolutely perfect across from the beach and 3 blocks from town! We will absolutely be back!!
Kimberly M.
Stayed 7 nights in Aug 2023
From a partner site
10/10 Excellent
Matthew S.
1 August 2023
Summer Vacation
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
House was clean, exceptionally well-stocked, and right across the street from the beach. Our family had a great time. Will hopefully return next summer.
Matthew S.
Stayed 7 nights in Jul 2023
From a partner site
10/10 Excellent
Debbie J.
28 June 2023
Great location in Cape Charles
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This location was perfect! We loved walking across the street to be on the best toddler beach ever. The house was very nice and spacious. The property manager was excellent and helpful. We would definitely stay here again.
The house is beautiful, location is walk across the street to beach access and local restaurants are great! We rented a golf cart from CC’s (amazing personnel) and that is a MUST for easy and convenient run abouts of the beautiful Cape Charles area! We have been to the Cape before but this stay was our absolute BEST! Will stay at this location again!
Rhonda S.
Stayed 3 nights in Sep 2022
From a partner site
8/10 Good
Greg W.
27 September 2022
Four days in by the Bay
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Great location. Large and comfortable house. Kitchen has a musty odor, suspect there is a water leak for issue in basement. Needs to be looked into.
Greg W.
Verified
10/10 Excellent
Paula H.
11 May 2026
Paula H.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 12 May 2026
Thanks for the rating! It was a pleasure hosting you — we’d love to welcome you back anytime.
About the host
Hosted by Chesapeake Properties Vacation Rentals
Languages:
English
Premier Host
They consistently provide great experiences for their guests