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Charming Historic 5-Bedroom Home with a Refreshing Pool!

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Fridge, microwave, oven, stovetop - Charming Historic 5-Bedroom Home with a Refreshing Pool! (Cape Charles)
Interior - Charming Historic 5-Bedroom Home with a Refreshing Pool! (Cape Charles)
5 bedrooms, iron/ironing board, WiFi, bed sheets - Charming Historic 5-Bedroom Home with a Refreshing Pool! (Cape Charles)
Smart TV, fireplace - Charming Historic 5-Bedroom Home with a Refreshing Pool! (Cape Charles)
Exterior - Charming Historic 5-Bedroom Home with a Refreshing Pool! (Cape Charles)
Cape Charles, a charming coastal town, is home to this light and bright historic house. Enjoy the private pool in this former Bed and Breakfast with updated decor where all bedrooms have private baths; perfect for families or those seeking some tranquility.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms6 bathroomsSleeps 144000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Charming Historic 5-Bedroom Home with a Refreshing Pool!

Escape to your ideal family retreat in the charming historic town of Cape Charles! This beautifully appointed home is just 5 blocks from the beach and a short 2 blocks away from delightful shops and restaurants. Previously a Bed and Breakfast, this spacious residence offers multiple bedrooms, each equipped with private baths, ensuring comfort for everyone in your family.

Spend time together in the large kitchen and inviting public areas, perfect for creating lasting memories. Enjoy the convenience of a pool to relax and unwind after fun-filled days at the beach. Plus, we understand that pets are part of the family! With prior approval, you can bring along your beloved furry friend (up to 60 lbs) with a $200 pet fee.

Accommodating up to 12 adults, this home is an ideal gathering spot for families and grandchildren. Note that all children over the age of 2 are considered adults in our guest limit. Explore Cape Charles by walking, biking, or taking a golf cart, with ample parking available for your convenience. Your family adventure awaits!

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Outdoor pool
  • Private hot tub

Internet

  • Available in the house: WiFi

Parking and transportation

  • Wheelchair-accessible parking and van parking available

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 5.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 accessible parking space
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In the city center
  • Near the sea

Things to do

  • Arcade/game room

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Property located in a resort
  • Unit size: 4,000 square feet

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  • Kitchen
  • Free WiFi
  • Air conditioning
  • Laundry
9.8 out of 10, Exceptional, 44 reviews
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includes taxes & fees
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Take out the trash
Turn off the lights and lock the doors
Trash Cans must be taken to the curb on Monday night.
Failure to complete these may result in a negative review from the host.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
1 total (up to 50 lbs per pet)

Children and extra beds

Children are welcome

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators

About the area

Located by the sea, this vacation home is in Historic Downtown Cape Charles, a neighborhood in Cape Charles. Eyre Hall and Chesapeake Bay Bridge-Tunnel are local landmarks, and the area's natural beauty can be seen at Kiptopeke State Park and Eastern Shore of Virginia National Wildlife Refuge. Visit our Cape Charles travel guide
View more Vacation homes in Cape Charles
Map
Cape Charles, VA

What's nearby

  • Afternoon Shadows at Cape Charles Beach
    Cape Charles Beach
    9 min walk - 0.8 km
  • Central Park
    1 min walk - 0.2 km
  • Cape Charles Museum & Welcome Center
    8 min walk - 0.7 km
  • Oyster Farm Marina
    14 min walk - 1.2 km
  • Bay Creek Golf Club
    6 min drive - 4.1 km

Getting around

  • Norfolk Intl. Airport (ORF)
    50 min drive

Restaurants

  • Small’s Smokehouse
    4 min drive
  • Hardee's
    5 min drive
  • McDonald's
    4 min drive
  • Top China
    5 min drive
  • Sting-Ray's Restaurant
    9 min drive

Frequently asked questions

Does Charming Historic 5-Bedroom Home with a Refreshing Pool! have a pool?

Yes, this property has an outdoor pool.

Is Charming Historic 5-Bedroom Home with a Refreshing Pool! pet-friendly?

Yes, this property allows pets (limit 1 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Charming Historic 5-Bedroom Home with a Refreshing Pool!?

Check-in begins at 4:00 PM.

What time is check-out at Charming Historic 5-Bedroom Home with a Refreshing Pool!?

Check-out is at 10:00 AM.

Where is Charming Historic 5-Bedroom Home with a Refreshing Pool! located?

Located in Historic Downtown Cape Charles, this vacation home is within a 10-minute walk of Central Park, Cape Charles Museum & Welcome Center, and Chesapeake Bay. Cape Charles Beach and Cape Charles Harbor are also within 15 minutes.

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Charming Historic 5-Bedroom Home with a Refreshing Pool! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 30 out of 30 reviews
Rating 8 - Good. 0 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Terri L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent host. Historical home with large bedrooms each with own full bathroom. Great for the family at Christmas.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

F.W T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our grandkids enjoyed the pool and the unique third floor bedroom. Great location near restaurants, shops and the beach. We will return.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Judith K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house in great location in Cape Charles!

Had a blast in comfort and convenience staying in Cape Charles with the whole family at Alyssa House. Lots of space, great pool, and ease of getting to any location in town on for or golf cart.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Rozenna P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time had by all!

What a nice time. The family had a great time.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Kristin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property!

We just adore Cape Charles! This house is a treat with your own private pool and bathrooms for every bedroom!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Lydia H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cape Charles

Cape Charles is a quaint town with lots to do for families. The property was perfect for our multi family vacation affording everyone privacy (with private bathrooms) along with plenty of family gathering rooms! We highly recommend!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Davis S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

As advertised!

This a great house in the heart of Cape Charles that is perfect for a large family stay. It is just as the pictures show , in great shape and was very clean on arrival. The owner was super pleasant and helpful through out our trip!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Nanette A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Beach Week

The house is perfect for extended family gatherings. Large kitchen, front and back porches, and a pool. Plenty of room for everyone to spread out. Plus every bedroom and a private bathroom.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

Everything was wonderful. This is our second summer staying in this house. It’s beautiful. Our family loves it.
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Debbie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect family vacation

Cleane, comfortable, spacious! Everyone loved the accommodations , convenience, walkability to beach and shops. One episode of fire alarm going off during the night which Kathy was responsive to!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Janet T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tucker family 2024 Cape Charles retreat

This was the perfect place for our family summer vacation house! All the bedrooms had full baths and was perfect all the families we had there. The pool was a plus because we have 3 or more days of over 100° heat index and a place to relax while the were babies napping. Definitely recommend for a large group!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Brandi K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our favorite place

We love the Alyssa house. Perfect location. Beautiful and clean. Kathy is friendly and responsive. Plenty of space and beautiful pool.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Diane W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Home in Cape Charles

We had a wonderful stay at Alyssa House in Cape Charles. The house is beautiful, so well appointed and well stocked. Everyone loved it. There was plenty of room for our family in the house. The yard and pool are fantastic. The location is perfect and the host is very responsive and helpful.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Deborah V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach escape

We celebrated my husbands birthday surrounded by family in this beautiful home. Kathy was a Perfect host and offered assistance with anything we needed. The town is quaint , friendly and the scenery is gorgeous. White sand beaches are in walking distance and there are shops, cafes and distilleries to enjoy. I loved the oysters at the distillery. I’d highly recommend this beautiful home for your next beach adventure
Stayed 9 nights in Nov 2023
Verified

10/10 Excellent

Sharon F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Was a very nice property for a large group. All bedrooms were comfortable and everyone having their own bathroom was a huge bonus. We enjoyed the hot tub. We were disappointed in the pool. It was dirty and we didn't get in. Felt we could of used some instruction on that. Overall it was a great stay.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Teresa L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was great. We loved the pool. It was nice to have so much made available to us so we didn’t need to pack as much, such as big beach towels. Kathy was extremely responsive.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Judith K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot all around!

Beautiful and comfortable home, close to town shops, restaurants, and the beach. In Cape Charles, nothing is more than a quick walk or brief golf cart ride away! Great house for a family looking to enjoy it all with a terrific host nearby and responsive.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Carla H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect! The house is clean, modern, historic, roomy, comfortable, magnificent. Everybody loved the pool. An easy walk to the beach, pier, shops, restaurants and the beautiful town park with playground. Something for everyone! Our hostess Kathy was the best! Would absolutely stay here again.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Meghann K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home!

This home was amazing for our large group of 3 families (6 adults, 6 kids). Everyone enjoyed the space and location on Alyssa’s House and Kathy was a very prompt and gracious host. We will be back!
Stayed 5 nights in Jun 2023
Verified

10/10 Excellent

Kristin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful, spacious house!

What a great house! The pool is such a treat! Close to Mason avenue and not too far from the beach! Golf carts & bikes make beach going easy! Kathy is great! We will be back!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Elizabeth V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious Cape Charles Home

Very comfortable and spacious home. Six updated bathrooms which everyone appreciated. Loved having the pool which we used everyday. Highly recommend!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Sharon W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacationing on the Eastern Shore

Alyssa House was perfect for our family! Plenty of bedrooms and baths for all 13 of us! Such a lovely historic home, beautifully decorated and so comfortable. We all enjoyed the pool and hot tub, the wonderful porches and making s’mores around the fire pit in the backyard! Kathy was a wonderful hostess and so helpful! We look forward to vacationing there again next summer and highly recommend Alyssa House!!!
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

carol m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kathy welcomed us upon arrival. Always available to make sure we were comfortable. House beautiful, spacious, modern upgrades with a touch of history. Close enough to beach to get some exercise and walk. We did rent golf cart though to get all beach supplies to beach. Short walk to town center and stores. Pool super refreshing! Large enough too for large family. Grateful for opportunity to stay here. Thank you again, Kathy!
Sunset
Castle in the sky
Hermit crab
In town
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Julie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay the week after Christmas through New Year’s Eve. Large fenced yard makes it extremely dog friendly. Although hard wood stairs were difficult for our older dog. House is beautiful. All bedrooms on 2nd and third floors. Every bedroom has a bathroom. Pictures don’t do it justice. It is thoughtfully appointed with towels, toiletries, paper towels, toilet paper and laundry supplies. Owner’s home is right next door. She is readily available to answer any questions and stopped by during our stay to talk to us about the various shops and restaurants available. When we couldn’t find a can opener, she brought one right over. Kathy is very helpful and the house is lovely.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

This house is so lovely and everything we needed was there. My sister and our families have been taking vacations together for the past 20 years up and down the east coast. This was our very favorite. We booked this house again while we were staying there. We range in ages 3 to 60 and it was hands down for a repeat at this house in Cape Charles. The hostess is the best.
Stayed 14 nights in Jul 2023