Classically Current - Chesapeake Properties

Top rated by guests
Private kitchen
Private kitchen
Private kitchen
Dining
Outdoor dining
review stars
9.8Outstanding
(84 Ratings)
"This house was perfect for our extended family vacation. There was plenty of space for three generations of family. We did most of our cooking at home and it was nice to have a screened-in porch to sp..."
Heather A.
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(84 Ratings)

House in Cape Charles, VA

13 guests · 6 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Summary:

"Classically Current" - lovely home on park and 4 blocks from beach! Come relax in our 100-year-old house, four short blocks from the Chesapeake Bay in charming Cape Charles, a turn-of-the-century railroad town on Virginia's Eastern Shore. The town is small, quaint and quirky with a variety of local activities.



Please SEE: Other Things to Note

For Area Details, Please SEE: Where You'll Be (Located under the map!)

*This is a no pet/animal home.



The Space:

Classically Current, Home Features:

• 6 Bedroom, 3.5 Bath - Available for up to 13 Guests!

• Screen Porch with Grill

• New Furnishings & Artwork Throughout

• High End Kitchen Appliances, 2 Ovens

• Free WiFi & Smart TVs



Third on Coastal Livings America's 10 Happiest Seaside Towns list for 2018. Great place for families or couples. Come enjoy the public beach, fishing pier, kayak tours, biking around town, or golf either a Nicklaus or Palmer course. Do a wine tasting at Chatham Vineyards, sample local beer at the Cape Charles Brewing Company, or sample spirits at the Cape Charles Distillery. You can enjoy lots of outdoor activity or just a lazy day around town.

The town continues to grow adding new shops and restaurants. Beautiful marinas and local watermen bring in fresh seafood at the Harbor.

The beautiful Victorian home is an easy walk to the beach and just 2 blocks from the main street Mason Avenue to experience shopping and restaurants.



The home has new furnishings and artwork throughout to create a calming environment for guests. Enjoy the entire home of just under 4000 square feet. Plenty of space and privacy to create happy memories. It has a wide staircase, pocket doors, 10 foot ceilings, original light fixtures, ceiling fans, and transom windows.



Amenities include- Smart TVs to stream your favorite show, 2G & 5G Wifi, three zone air conditioning, and on demand hot water.

Expansive front porch to enjoy with friends and family. Or sit on the screened in back porch overlooking the park watching the children play or enjoying local concerts and events.



Private parking off the alley behind the home for 2 cars.



1st floor

Nicely appointed kitchen with high end appliances including two ovens.

New Weber propane grill on the screened in porch.

Large dining table for large gatherings post a day at the beach.

Family room with plenty of seating and a TV.

Parlor can be closed off to use as another sleeping location or to quietly read a book.

Half bath under the stairs for guests.



2nd floor

Beautifully appointed master bedroom with king bed, walk in closet, and private bath with shower and soaking tub. Queen bedroom with large windows overlooking the quiet street.

Twin bunk room for the children.

Queen bedroom with balcony. Sit in the rocking chair overlooking the park off this bedroom.

Bathroom with shower.

Laundry room with full size washer and dryer.



3rd floor

Large area for games and wet bar with view of the Bay.

Full bathroom and two additional bedrooms. The bedrooms have a full and a twin.



Outdoors

Includes propane grill, plenty of outdoor seating, screened in porch with ceiling fan, beach chairs, a beach umbrella, 2 bikes, and small sand toys.

The rental of the home includes linens, towels, beach towels, and Internet/WiFi. No smoking or pets.





Classically Current rents by the week in summer (Sat-Sat). Reservation requests other than full weeks in summer or for off-schedule arrivals are not allowed through online booking. Give us a call if you are interested in a shorter stay! Enjoy the home with a 2 night minimum outside the summer season.



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.



• We cannot guarantee early check-ins or late check-outs, as both are subject to availability. Please contact us 24 hours prior to check-in to submit your request.



Classically Current rents by the week in summer (Sat-Sat). Reservation requests other than full weeks in summer or for off-schedule arrivals are not allowed through online booking. Give us a call if you are interested in a shorter stay! Enjoy the home with a 2 night minimum outside the summer season.



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!

• Local Restaurants & Shopping

- Restaurants: The Shanty, Oyster Farm Seafood Eatery, Kelly's Gingernut Pub, Pane e Vino, Ambrogia Caffe & Enoteca, Cravings, Beach Market

- 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!



Northampton County Short-Term Rental Registration No. #



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:

• Taxi Cabs [i.e., Cape Charles Cab Cart and Carriage, Champion Cab, Rudy's Taxicab Services]

• STAR Transit, local fixed route and bus service

• Uber, Lyft

• 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 Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host.

- 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.

- 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.

Amenities at Classically Current - Chesapeake Properties

Non-smoking
Family friendly

Map of Cape Charles, VA


Ratings and reviews

9.8 / 10
Outstanding(84 Ratings)
10 / 10Outstanding·Aug 2025
This house was perfect for our extended family vacation. There was plenty of space for three generations of family. We did most of our cooking at home and it was nice to have a screened-in porch to spread out at dinner. Backing up to the park was an ideal location. We could even hear the saturday night concert from the porch. The house is clean, comfortable, and lovely and we would absolutely stay there again.
8 / 10Excellent·Aug 2025
The size and layout of the house was perfect for a large family with kids of all ages. The location is perfect as the park is right behind the house and the kids could ride their bikes, play on the playground or play tennis or pickleball almost within sight. The distance to the beach is walkable, and we rented a golf cart which was helpful for getting lots of gear to the beach. It was unfortunate that the ice maker in the frig did not work and despite multiple emails to the rental company it was never addressed, even though they said they would send someone to check on it. We ended up buying bags of ice for the freezer. The listing says they have beach towels at the house so we did not bring any - there were no beach towels at the house. After a lot of back and forth, they agreed to bring us beach towels, which they did, so that problem was solved. None of the instructions told us you have to come and go from the back door - you have to lock the front doors from the inside - it was confusing when we arrived as we thought we had the wrong keys. There also remains confusion over alley parking between the welcome email, the on line listing and the check in paper, (0-2 cars). The little house on the property that sits behind the big house is quite close and had 2 bright spot lights on every evening and overnight that shone directly into the back of the big. house. It felt especially invasive while on the screened in porch where we worked on a puzzle each evening.
10 / 10Outstanding·Dec 2024
We have booked this property now three times for our large family and it's perfect for us everytime! Will book again next year.
10 / 10Outstanding·Sep 2024
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 home is magnificient! The rooms are so spacious, the location is so close to the park and a nice walk to the beach. Home was spotless! There was not one thing I would change. We will be renting it again next year!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Classically Current - Chesapeake Properties. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Classically Current - Chesapeake Properties pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Classically Current - Chesapeake Properties?

We found 2 amenities for this rental. This includes non-smoking, and family friendly.