Machipongo Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Machipongo

Modern Suite in Historic Building Two Blocks to Beach
9.8 out of 10, Exceptional, (51)
"Loved the details in this smaller but totally functional property. Host was attentive and helpful and the the room was just off the Main Street in Cape Charles. We lived it. The heated bathroom floor was a sweet bonus!"
Modern Suite in Historic Building Two Blocks to Beach
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (113)
"This is a great place to kayak and get away from city noise! You hear only the wildlife, hunting dogs raised by the neighbor, and a few fishing boats. The house is well stocked, a back up of paper supplies such as toilet paper and paper towels would be helpful. We spent the majority of our time on the screened-in porch in the rocking chairs and at the picnic table - amazing! The afternoon sun hits the other side of the house, so you can enjoy the porch all day long! I would agree with a...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Modern Suite in Historic Building Two Blocks to Beach
9.6 out of 10, Exceptional, (38)
"Property was great. Loved the heated floor. There is a coffee maker not a keurig— would bring items for coffee if it’s a must. Could hear some noise from the pub next door but it did not last past 9pm. Clean and located such that you could walk right to the Main Street."
Modern Suite in Historic Building Two Blocks to Beach
Save an average of 15% on thousands of hotels when you're signed in
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
9.6 out of 10, Exceptional, (123)
"We enjoyed our first time in Cape Charles and hope to go back to spend more time. This rental is a very charming older home in a neighborhood filled with the same! The home had everything we needed inside and landscaping and w wonderful front porch to enjoy outside. Loved that we could park the car and walk to shops, restaurants and to the beach. Looking forward to another visit."
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, (31)
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
9.8 out of 10, Exceptional, (126)
"Nice property. Great location."
The Crows Nest. <br>Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
Sisters 3 by the Sea, 400 Feet To The Beach
9.4 out of 10, Exceptional, (134)
"This was a great location for our family. We walked The short distance to the beach every day! Also spent time at the pier fishing half mile down the beach."
The price is NZ$1,124
includes taxes & fees
29 Jun - 30 Jun
Sisters 3 by the Sea, 400 Feet To The Beach
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
10.0 out of 10, Exceptional, (179)
"This place is truly AMAZING! My family and I had a wonderful time! Our dog Walter absolutely loved it and it is overall just a wonderful place. This will for sure be a place we continue to come stay at every year."
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
Waterfront, Private Dock, Fire Pit, Hot Tub, Screened Porch and Beach Access!
10.0 out of 10, Exceptional, (22)
"Great property, everything was just as described in the listing, the house had everything we needed in it. The outdoor space was a huge hit for our kids who fished and enjoyed the hot tub and fire pit. Plenty of sleeping space and linens available, house was very clean and well kept. We will definitely be back this summer!"
Waterfront, Private Dock, Fire Pit, Hot Tub, Screened Porch and Beach Access!
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
9.4 out of 10, Exceptional, (142)
"The stay was great if you don’t mind cameras watching you. Propane tank was empty, couldn’t sit on balcony because straw would go up my ass from the crappy chairs. Stove top was dirty with mysterious fluid. It was what it was. Plenty to do in area. Plenty of undersize crab available- we threw them back."
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK
Cute and Cozy Vacation Stay on the Eastern Shore!
8.8 out of 10, Excellent, (52)
"Tv only had one channel and floors were very dirty but I bought mop and cleaned them up not a problem everyone there I spoke to was very nice"
Cute and Cozy Vacation Stay on the Eastern Shore!
The most affordable BEACHFRONT vacation rental in Cape Charles!
9.4 out of 10, Exceptional, (32)
"My sisters, mom and I decided that cape Charles was a half way point to meet for a long weekend. The house was more affordable than others, it had a nice layout with a few places to sit and hang out. Our favorite was the sun room. Furniture is outdated but the space was perfect and we enjoyed our coffee there. The outdoor seating was great as well and we spent a few evenings out there as well . A short walk to town and a short walk to The beach. Parking was fine on the street for all 3 cars....
The most affordable BEACHFRONT vacation rental in Cape Charles!
Welcome to our charming vacation home in the historic district of Cape Charles!
10.0 out of 10, Exceptional, (1)
"We enjoyed our weekend stay in Cape Charles in this charming, quaint, and historic home. It felt like a step back in time, while enjoying modern efficiencies. The grill was convenient and we enjoyed the pool table in the game room. The linens and living areas were clean and the kitchen was well stocked with dishes, utensils, pots, pans, etc. The property manager was pleasant, communicative, and responsive. The only minor suggestions I have would be to have the cleaning crew set a reasonable...
Welcome to our charming vacation home in the historic district of Cape Charles!
Room for the Whole Family or Several Families and Just a Walk to the Beach
9.0 out of 10, Wonderful, (45)
"Great place to stay. Not too far from the beach and very close to a great little town with great shops."
Room for the Whole Family or Several Families and Just a Walk to the Beach
Cape Utopia - sister to existing ID# 7559899
9.6 out of 10, Exceptional, (23)
"We surprised my mom with a trip to Cape Charles. She had never been. so she was delighted. We have stayed at this location before. It is perfect for us. 😊 the house has so much charm and they have thought of everything you could possible need and more. This is our first choice when coming to Cape Charles. See you next trip. 😊"
Cape Utopia - sister to existing ID# 7559899
New Home On Rural Eastern Shore Farm
9.8 out of 10, Exceptional, (73)
"We have a group of senior men here to play golf. Exactly what we need and a great location."
New Home On Rural Eastern Shore Farm
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach
9.8 out of 10, Exceptional, (21)
"My father and I attended my niece's wedding in Cape Charles. We enjoyed our stay and everything was as advertised. Very clean and tidy. I would recommend this house to anyone looking for a nice, clean and quiet place to stay. It is about a mile or so outside of town."
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach
Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.
10.0 out of 10, Exceptional, (54)
"This was our second time staying at the Cozy Cottage. We enjoyed it just as much as the first time. This house has everything you need. Will look to stay here again in the future!"
Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
9.8 out of 10, Exceptional, (31)
"Very convenient location and quite close to the beach."
Cape Haven -Condo 1.5 Blocks from Beach, New Roof Top Deck!
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops
10.0 out of 10, Exceptional, (39)
"The houses location to the downtown area and beach were incredible! We rented a golf cart and didn’t have to get back in our car after parking it! The house had everything we could think of and is such a charming place! The fenced yard could not have been better for our doggo and the game barn was perfect for one of the colder days! We will definitely be back!"
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops
Don't see what you're looking for?
See all available properties in Machipongo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Machipongo you may be interested in

Shore Stay Suites
2.0 star property
8.4 out of 10, Very good, (468)
"Spacious rooms, full kitchen and clean!"
The price is NZ$204
includes taxes & fees
4 Jun - 5 Jun
Shore Stay Suites
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (627)
"Great experience!"
The price is NZ$225
includes taxes & fees
2 Jun - 3 Jun
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
Hampton Inn & Suites Exmore - Eastern Shore
2.5 star property
8.4 out of 10, Very good, (849)
"Not much in the area"
The price is NZ$227
includes taxes & fees
31 May - 1 Jun
Hampton Inn & Suites Exmore - Eastern Shore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Machipongo holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Machipongo. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Machipongo. Seeing all the best attractions is bound to make you fall in love with Machipongo. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Machipongo short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Machipongo?

Yes, there are holiday rentals close to the most popular sights in Machipongo, or you can select a more secluded option if you're looking for a relaxing stay. Machipongo is known for its museums.

How many holiday rentals will I find in Machipongo?

Choose from 4 Expedia holiday rentals in Machipongo for a memorable holiday.

What’s there to see and do in Machipongo?

Cultural attractions to visit include Barrier Islands Center and Barrier Island Museum. In the wider area, you’ll find Chatham Vineyards and Cape Charles Beach.

What’s a holiday rental in Machipongo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Machipongo. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for family trips or small group gatherings.

Recent reviews of Machipongo properties
Expedia verified reviews