Machipongo Holiday Rentals

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Holiday Rentals in Machipongo

Bay cottage, Beach 100 yards away! RESERVE NOW!!!

9.6 out of 10, Exceptional, (129)
"Loved everything about this lovely cottage and especially walking to the bay! Rick was extremely kind and helpful. Hope to come back!"
The price is AU$734
includes taxes & fees
1 Dec - 2 Dec
Bay cottage, Beach 100 yards away! RESERVE NOW!!!

Waterfront Cottage with Private Beach, Sunsets over Water

10.0 out of 10, Exceptional, (194)
"The house was very clean upon entering and the view was beautiful. It was conveniently located to shops and restaurants. We enjoyed visiting the nearby Hatchery while there. "
Waterfront Cottage with Private Beach, Sunsets over Water

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool

Private, 7-acre waterfront retreat on Winter Harbor Haven

10.0 out of 10, Exceptional, (122)
"Family and dog had a wonderful time at this off-the-beaten path waterfront gem. Great water access and beautiful views from the screened porch. Enjoyed crabbing, beach walks at nearby preserve, sunrises, quaint town w cute shops."
Private, 7-acre waterfront retreat on Winter Harbor Haven

Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

9.4 out of 10, Exceptional, (151)
"This was exactly what I was looking for. The Property is very private and the yard surrounding the house was huge. I found it comfortable and cozy. Randy was very accommodating and asked that you respected his property and clean up after yourself and your pets which is to be expected were I come from, a small ask. He had plenty to offer. The private dock and water access was perfect and being able to us his canoes and kayaks was a very nice extra. One of my favorite things was the very large...
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

BEACHFRONT COTTAGE JUST STEPS AWAY FROM BEACH!

9.4 out of 10, Exceptional, (34)
"We loved Cape Charles for it's laded back environment. House was a 1960's property but it had everything you need and more."
BEACHFRONT COTTAGE JUST STEPS AWAY FROM BEACH!

Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

10.0 out of 10, Exceptional, (13)
"Clean, welcoming home with huge backyard for kids to play in! Firepit was a big hit. Very easy access to Cape Charles (it's literally right down the road) and right off 13. Great place for a great time... we loved it! all 10 us!"
Minutes to the BEACH! Large yard w/fire pit, bocci, ample parking and fun!

Room for the Whole Family or Several Families and Just a Walk to the Beach

9.0 out of 10, Wonderful, (49)
"We were underwhelmed by the home. On the positive, lovely historic home in great proximity to everything. Negative, house smells of pet urine, carpets had urine stains, kitchen floor was disgusting, utensils needed to be washed before using, dishwasher had food in the bottom. No dish washer detergent was provided. The back porch needs power washing and repair. There is no hot tub or jetted tub as advertised. It is a duplex… not a single family home "
Room for the Whole Family or Several Families and Just a Walk to the Beach

Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

10.0 out of 10, Exceptional, (18)
"Even though we were there off-season for a wedding, this VRBO is super close to the beach. Also close is a grocery store. Only possible issue is a super squeaky floor in master bedroom could disturb a light sleeper or a baby. Kitchen is masterfully stocked, great deck, quiet neighborhood, awesome water pressure (although you may prefer bottled water due to the minerals). You'll need to bring your own shampoo as well. It was perfect for our needs and super cute!"
Newly renovated, 4BD 2 BA, 1 full acre, sleeps 9, and is pet friendly.

Sunflower Cottage - Waterfront; Outdoor shower!

10.0 out of 10, Exceptional, (3)
"We had a wonderful time and the cottage had everything we could need. The backyard and Bay Area is beautiful. We will definitely be booking here again"
Sunflower Cottage - Waterfront; Outdoor shower!

Seas the Day at Bay Creek - Pet Friendly & Linens Included!

9.6 out of 10, Exceptional, (5)
"The place was perfect for our mixed group of 8 and a dog. Highly recommend! "
Seas the Day at Bay Creek - Pet Friendly & Linens Included!

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

10.0 out of 10, Exceptional, (54)
"Can't say enough about our experience at the house! Location is top notch. House was perfect to accommodate our large group. Kitchen was stocked with every9int and more to make all your meals. It was nice having a big outdoor area to dump our beach gear and run around with the kids. If our group was not expanding due to kids we would come back here every year. We loved what felt like a private beach too. I think most will agree, the access to the beach is not the best but I assume that is...
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops

10.0 out of 10, Exceptional, (46)
"The owners have done a great job renovating an historic home. It was clean, comfortable and had all the little things we needed. It was 95 so we did spend much time in the party barn, but it was a great place to hang out after dark. We were worried about 1.5 bathrooms, but the outdoor shower was nice, and I don't think anyone showered inside. Great house and great location."
Game Barn! Next to Central Park! 2 Blocks 2 Beach/Resturants/Shops

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (23)
"The entrance right into the bed, a mere foot from the door with the mop and cleaning supplies to the right of the door did not give a great first welcoming. The smells indicated either mustiness or seafood in the fridge or both.Yes there were air freshener candles but, deep cleaning may be best to get to the root of it. The WiFi was not correct-the links that popped up were not in sync w/what was in the binder of info. When reached out to property manager for both entry inquiry and wifi, he was...
Perfect Cozy Vacation Rental on the Eastern Shore

Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

9.8 out of 10, Exceptional, (30)
" We really enjoyed our time in Cape Charles and staying in Sea Cottage. It was clean, comfortable and just a sweet little house. It is located just a couple miles from downtown Cape Charles, but quickly and easily accessible to everything. For those with any mobility issues there are a few steps to get in and then inside there are two steps between the two sections of the house. There is a large walk in shower that was nice to use. We will definitely stay here again. "
Sea Salt Cottage: Your Tranquil Getaway 3 min to beach

Cape Utopia - sister to existing ID# 7559899

9.8 out of 10, Exceptional, (31)
"What a great trip! Our first trip to the Eastern Shore and it won't be out last. What a terrific VRBO. It had everything we needed and more. Loved the historic home. Our host, Elizabeth, was attentive and welcoming. We will be back to Cape Charles and we will return to this home. The location was centrally located and we enjoyed our walks to the beach and to the main street area. Can't recommend more highly!"
Cape Utopia - sister to existing ID# 7559899

Cute and Cozy Vacation Stay on the Eastern Shore!

8.8 out of 10, Excellent, (57)
"Very convenient to where we were most of the trip."
Cute and Cozy Vacation Stay on the Eastern Shore!

4 min walk to beach, Dog Friendly, Fenced Yard, Firepit, Fireplace,

9.6 out of 10, Exceptional, (38)
"Fantastic location! Backyard is ideal. Love that they allow dogs!"
4 min walk to beach, Dog Friendly, Fenced Yard, Firepit, Fireplace,

Cape Haven - Condo 1.5 Blocks from Beach

9.8 out of 10, Exceptional, (41)
"The condo is very cute with a wonderful kitchen. Very clean with a nice deck. Be aware that the deck faces out over a back alley. The only water view is from the deck on the roof, which is spectacular! The location is wonderful. You can walk to everything and all over the town. Beach is just down the street. The condo is between two buildings so both bedrooms look out at a brick wall. Lots of games provided. The bikes really don't work. Love the town and enjoyed great food. "
Cape Haven - Condo 1.5 Blocks from Beach

Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach

10.0 out of 10, Exceptional, (19)
"We had an incredible weekend in Cape Charles at Drop Anchor. We've been renting places in CC for the past 10 years, and this was the cleanest and most well-appointed home we've ever rented. My husband and I invited 4 friends to CC for the weekend bc they had never been, and they fell in love with everything! The golf cart was amazing, and we had the best time. Timely responses and detailed notes and emails from property manager. Thank you so much for having us at Drop Anchor! We’ll definitely...
Cape Charles Newly Updated Family-friendly Beach House, 1 Block to Private Beach
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.
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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, (545)
"We’ve stayed here several times. It is clean and affordable. We like having the mini-kitchen/full fridge. Convenient to drive to Cape Charles and Kiptopeke. Will definitely be back. "
The price is AU$187
includes taxes & fees
27 Nov - 28 Nov
Shore Stay Suites

Hampton Inn & Suites Exmore - Eastern Shore

2.5 star property
8.4 out of 10, Very good, (922)
"I loved it"
The price is AU$125
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn & Suites Exmore - Eastern Shore

Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel

2.5 star property
8.2 out of 10, Very good, (688)
"We stop here every year on our way through to the Outer Banks. Clean, comfortable, friendly & reasonably priced. Perfect for a quick overnight stay. Oh, breakfast is a nice plus too!"
The price is AU$141
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.

What are some of the best holiday rentals that Machipongo has to offer?

The Crows Nest.
Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!
: This holiday home rental outside of Machipongo is located on the waterfront, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

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 include Barrier Islands Center and Barrier Island Museum, whereas Webbs Island and Horse Island are a couple of picturesque spots to enjoy the outdoors. In the wider area, you’ll find Chatham Vineyards and Eyre Hall.

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.