Entire home
Fins Up - Chesapeake Properties
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Reviews
8.8 out of 10
Excellent
2 bedrooms3 bathroomsSleeps 6
Popular amenities
Explore the area

Cape Charles, VA
- Place, Central Park1 min walk
- Place, Cape Charles Beach9 min walk
- Place, Oyster Farm Marina12 min walk
- Airport, Norfolk, VA (ORF-Norfolk Intl.)50 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
2 Single Beds and 1 Queen Bed
3 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
Dining area
About this property
Fins Up - Chesapeake Properties
Summary:
Charming Coastal Escape Just Steps from Downtown Cape Charles! Fins Up offers a comfortable Cape Charles retreat just two blocks from downtown! This charming duplex features a spacious layout, private balconies, a cozy fire pit, and easy access to shops, dining, and the beach—perfect for a memorable coastal escape.
Please SEE: Other Things to Note
For Area Details, Please SEE: Where You'll Be (Located under the map!)
*Pet Friendly, fee applies per pet.
The Space:
Fins Up, Home Features:
• 2 Bedroom, 3 Bath - Available for up to 8 Guests!
• Well-Equipped Kitchen
• Games, Books & Cozy Seating
• Shared Backyard with Fire Pit
• Free WiFi & Smart TVs
Experience simplicity and charm at Fins Up, a duplex tucked away on a quiet street yet only two blocks from downtown Cape Charles. Start your mornings on the front porch, where a rocking chair and a fresh cup of coffee make the perfect setup for watching golf carts buzz by as families head to the beach!
Step inside to a spacious, open-concept living area that flows into the dining room and fully equipped kitchen. With games, books, and cozy seating, it’s an ideal space to relax and make memories with loved ones.
Upstairs, two large bedrooms offer plenty of comfort and privacy. The primary king suite features a private bathroom and its own front balcony. The second bedroom includes a queen bed, a twin daybed with a trundle, a private bathroom, and a back balcony with a view of the concerts in Central Park. Both rooms provide ample storage, plus there’s a convenient hallway closet with a washer and dryer.
End your day in the shared backyard, a perfect spot for unwinding after exploring Cape Charles. Grill dinner, gather around the fire pit, or just relax and listen to live music from the park.
Fins Up is the ideal home base for your Cape Charles vacation—quiet, comfortable, and close to everything!
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:
Most who visit fall in love within a few minutes! 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 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 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.
Charming Coastal Escape Just Steps from Downtown Cape Charles! Fins Up offers a comfortable Cape Charles retreat just two blocks from downtown! This charming duplex features a spacious layout, private balconies, a cozy fire pit, and easy access to shops, dining, and the beach—perfect for a memorable coastal escape.
Please SEE: Other Things to Note
For Area Details, Please SEE: Where You'll Be (Located under the map!)
*Pet Friendly, fee applies per pet.
The Space:
Fins Up, Home Features:
• 2 Bedroom, 3 Bath - Available for up to 8 Guests!
• Well-Equipped Kitchen
• Games, Books & Cozy Seating
• Shared Backyard with Fire Pit
• Free WiFi & Smart TVs
Experience simplicity and charm at Fins Up, a duplex tucked away on a quiet street yet only two blocks from downtown Cape Charles. Start your mornings on the front porch, where a rocking chair and a fresh cup of coffee make the perfect setup for watching golf carts buzz by as families head to the beach!
Step inside to a spacious, open-concept living area that flows into the dining room and fully equipped kitchen. With games, books, and cozy seating, it’s an ideal space to relax and make memories with loved ones.
Upstairs, two large bedrooms offer plenty of comfort and privacy. The primary king suite features a private bathroom and its own front balcony. The second bedroom includes a queen bed, a twin daybed with a trundle, a private bathroom, and a back balcony with a view of the concerts in Central Park. Both rooms provide ample storage, plus there’s a convenient hallway closet with a washer and dryer.
End your day in the shared backyard, a perfect spot for unwinding after exploring Cape Charles. Grill dinner, gather around the fire pit, or just relax and listen to live music from the park.
Fins Up is the ideal home base for your Cape Charles vacation—quiet, comfortable, and close to everything!
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:
Most who visit fall in love within a few minutes! 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 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 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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9.8 out of 10, Exceptional, (116 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Charge may apply
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
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 by the sea. The area's natural beauty can be seen at Kiptopeke State Park and Eastern Shore of Virginia National Wildlife Refuge, while Cape Charles Museum & Welcome Center and Barrier Island Museum are cultural highlights. Explore all the area has to offer with horse riding and cycling.

Cape Charles, VA
What's nearby
- Central Park - 1 min walk - 0.1 km
- Cape Charles Beach - 9 min walk - 0.8 km
- Cape Charles Museum & Welcome Center - 9 min walk - 0.8 km
- Oyster Farm Marina - 12 min walk - 1.1 km
- Bay Creek Golf Club - 6 min drive - 4.5 km
Getting around
Restaurants
- Small’s Smokehouse - 4 min drive
- Hardee's - 5 min drive
- McDonald's - 4 min drive
- The Shanty - 10 min walk
- Sting-Ray's Restaurant - 9 min drive
Frequently asked questions
Reviews
8.8
Excellent
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
This review is from a guest who booked and stayed through a partner site and can't be verified.
29 June 2021
Stayed 7 nights in Jun 2021
10/10 Excellent
carl w.
3 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
carl w.
Stayed 3 nights in Aug 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nancy B.
21 Oct 2021
Appropriately named - Sit a Spell is lovely
Nancy B.
10/10 Excellent
Elizabeth G.
12 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Elizabeth G.
Stayed 7 nights in Jul 2022
This review is from a guest who booked and stayed through a partner site and can't be verified.
2/10 Terrible
marcie c.
30 Nov 2021
Perfect for a Family Getaway
marcie c.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Colleen Ann T.
9 Aug 2021
Wonderful home!
Colleen Ann T.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Frans M.
21 June 2021
Very hospitable and comfortable
Frans M.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Jason G.
18 May 2021
Cape Chuck perfection!
Jason G.
About the host
Hosted by Chesapeake Properties
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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