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Chesapeake Charm Estate, Two Blocks from the Beach

House in Cape Charles, VA

14 guests·6 bedrooms·5 bathrooms
5.0 · 60 reviews

Why you'll love this stay

Location & Accessibility

Location & Accessibility

Walkable to the beach and downtown, ideal for multi-generational trips.

Outdoor Living

Outdoor Living

Expansive outdoor spaces and a welcoming front porch for gatherings.

Style & Comfort

Style & Comfort

Elegant coastal interiors blend historic charm with modern comfort.

Property details

Discover the timeless elegance of Chesapeake Charm, a spacious 1920 Foursquare home just two blocks from the serene Chesapeake Bay in Cape Charles. With 6 bedrooms, 5.5 bathrooms, and a perfect blend of historical details and modern comforts, this luxurious retreat is the ultimate getaway for families or groups seeking relaxation near the beach and downtown attractions. Please see: Other Things to Note For Area Details, please see: The Neighborhood & Getting Around *This is a no pet/animal home. Quiet hours: 22:00 to 8:00. Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Suitable for: children and infants Chesapeake Charm, Home Features: • 6 Bedrooms, 5.5 Baths, up to 12 guests • Prime Location Near the Beach and Downtown • Spacious and Luxurious Layout • Outdoor Oasis and Additional Comforts • Free WiFi & Smart TV Welcome to Chesapeake Charm, a beautifully preserved American Foursquare home built in 1920, located just two blocks from the tranquil Chesapeake Bay in the heart of Cape Charles. Situated in a golf cart-friendly neighborhood, this home offers the perfect combination of historical elegance and modern amenities, making it an ideal retreat for families or groups. Spanning 3,600 square feet, the home features six spacious bedrooms and 5.5 bathrooms, providing plenty of room for everyone to relax and unwind. The main floor boasts two inviting living areas, a formal dining room with an original fireplace, a fully equipped kitchen with ample storage, a small game room with a foosball table, a laundry room, and a convenient half bath. Upstairs, the second floor offers three luxurious bedrooms, two with king beds and one with a queen, all with brand-new furnishings and en-suite bathrooms. The third floor is a charming hideaway perfect for kids, complete with a full bath and stunning views of the Chesapeake Bay. In the private guest suite at the back of the home, you'll find two additional bedrooms, including a queen and a full-size bunk bed, along with a shared full bathroom. Outside, the lush gardens, private deck, and spacious backyard create a serene outdoor oasis. A brand-new outdoor shower is perfect for rinsing off after a day at the beach, and the home is equipped with beach chairs and umbrellas (8 chairs and 2 umbrellas) for your convenience. Off-street parking, accessible via the alley, ensures ease of access throughout your stay. Chesapeake Charm is located just nine houses from the beach, where calm, quiet waters provide a safe and enjoyable spot for little ones to play or for peaceful sunset strolls. After your beach adventures, take a short walk to Cape Charles' charming downtown, where you can enjoy delicious dining, shop for souvenirs, and treat yourself to something sweet at the local candy store. Whether you're planning a family vacation, a reunion, or simply a relaxing escape, Chesapeake Charm offers everything you need for an unforgettable stay. We look forward to welcoming you and your group to experience the history, beauty, and charm of Cape Charles. This home uses keyless entry for self-check-in; your door code is sent by email and text 2 weeks (or less) prior to arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. 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. We follow the CDC Recommended Cleaning Guidelines. You can rest assured this property has been completely sanitized prior to check-in. • 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. 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. # Please pay close attention to following the house rules. Non compliance could result in sizable fines. • All guests staying at a Chesapeake Properties Vacation Rentals by Portoro are required to sign (e-signature) 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.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

3 Single Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Bunk Bed

Bedroom 6

1 Queen Bed

What’s included

  • Self check-in

    Self check-in

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

  • Balcony

    Balcony

Guest reviews

Star icon 5.0 | 60 reviews
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K

Kelly

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April 2025

Was a large house for multiple families and close to the beach.

E

Erin

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August 2024

This is the third year we've stayed at Sweet Retreat and we hope to be able to return for many more years. The house is comfortable and set up perfectly for a multi-generational extended family gathering and the location is quiet but still walkable to both the beach and Main Street restaurants and shops. We've made many lovely memories here and so appreciate Phillip and his family's willingness to share their home.

C

Caroline

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July 2024

Our group of three families had a wonderful stay. The house was spacious and had everything we needed for a week away from home. The hosts were extremely responsive too. Overall, our week away couldn’t have been better and we would absolutely stay again!

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⁨P.K.⁩

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June 2024

Really responsive hosts. We would stay here again. Lots of room for three families and kids.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

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