Machipongo Vacations from $348

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Your Machipongo Vacation

Create a custom vacation package to Machipongo and get ready for your next big adventure. Consider basing yourself in the neighborhood of Oyster, which is great for views and walking, for a true taste of this interesting city. If your trip to Machipongo includes a little sightseeing, take in renowned attractions like Barrier Islands Center, Chatham Vineyards and Barrier Island Museum. Whatever your travel plans or budget, putting together the ultimate tailored Machipongo vacation is simple with Expedia.

The Latest Machipongo vacation packages

Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier
Price was $447, price is now $348 per person
$348
per person
Feb 19 - Feb 23
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.6/10 Excellent! (329 reviews)
Nice clean hotel.. only little thing that bothered me was the $100 additional deposit for hotel food or beverages.. but was immediately returned after the stay so overall I was pleased.

Reviewed on Jan 4, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $1,794, price is now $940 per person
$940
per person
Mar 7 - Mar 10
found 12 hours ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
No reviews
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $1,403, price is now $992 per person
$992
per person
Feb 15 - Feb 19
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,478 reviews)
We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday

Reviewed on Oct 12, 2025

The Landing at Hampton Marina, Tapestry Collection by Hilton

The Landing at Hampton Marina, Tapestry Collection by Hilton

3.5 out of 5
Downtown Hampton
Save 100% on your flight
Price was $711, price is now $530 per person
$530
per person
Feb 19 - Feb 23
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8/10 Very Good! (1,000 reviews)
Great staff and location.

Reviewed on Dec 31, 2025

Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Save 100% on your flight
Price was $992, price is now $746 per person
$746
per person
Feb 19 - Feb 23
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
9/10 Wonderful! (1,000 reviews)
We checked in about 5:45, were never told our room number or how to get to our room. The front desk seemed annoyed we were even there. The information for the restaurants on site was not correct. We went upstairs to the Grain for HH which was nice our appetizer took almost an hour to come out, we closed out to go to dinner at downstairs restaurant and the bartender was inattentive. We finally decided to go back to our room for wine and asked the front desk for a wine key which they said no too. We called about another concern and was told no manager was on duty. Will not be hosting another girls night there.

Reviewed on Jan 4, 2026

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Discover the most popular places to visit in Machipongo

Chatham Vineyards

You can enjoy a tasting or tour at Chatham Vineyards during your travels to Machipongo. Wander the beaches or discover the area's sunrises.

Chatham Vineyards

Barrier Island Museum

You can spend time studying the exhibits at Barrier Island Museum during your trip to Machipongo. While you're in the area, stroll along the beautiful beaches.

Barrier Island Museum

Machipongo Hotel Deals

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

2.5 out of 5
3446 Lankford Hwy Exmore VA
Fully refundable
$83 nightly
The price is $92 total per night from Jan 7 to Jan 8
$92 total
Jan 7 - Jan 8
Total with taxes and fees
8.4/10 Very Good! (790 reviews)
Breakfast was fresh and customer service was excellent

Reviewed on Dec 27, 2025

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy Exmore VA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Jan 16 to Jan 17
$99 total
Jan 16 - Jan 17
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Parking was safe. Breakfast needs lots of improvement. Eggs are not edible, sausage’s instead of baked, fresh fruit needs to be fresh not mushy. Choose a better choice for muffins and danish.

Reviewed on Dec 29, 2025

Hampton Inn & Suites Exmore - Eastern Shore
Perfect Cozy Vacation Rental on the Eastern Shore

Perfect Cozy Vacation Rental on the Eastern Shore

Cape Charles VA
8/10 Very Good! (27 reviews)
Location was perfect, ample parking.

Reviewed on Nov 10, 2025

Get rates
Perfect Cozy Vacation Rental on the Eastern Shore
See all 472 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.

Find the Best Machipongo Vacation Packages

Machipongo Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Cape Charles Beach, Barrier Islands Center and Chatham Vineyards

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Frequently asked questions

How much does a Machipongo vacation package cost?
Offering excellent value package deals from $348 on Expedia, you'll be pleasantly surprised at how much a vacation to Machipongo costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Machipongo?
You can typically find lower rates and better availability in November, December and January. Browse our cheap Machipongo vacation packages and you could land some great off-season discounts.
How many days is enough for Machipongo?
Usually, a handful of days is great for a Machipongo vacation. With a carefully crafted itinerary, you can check out all the main sights including Barrier Island Museum, as well as explore some hidden gems along the way.
How to find the best Machipongo package deals?
Use Expedia's filter tool to help you find some of the best Machipongo package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Machipongo package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Machipongo vacation as a package?
You can enjoy significant savings on your Machipongo escape by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Machipongo?
Score incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Machipongo getaway.
Does Expedia offer Book Now, Pay Later Machipongo vacation packages?
Jet off on your dream escape to Machipongo with our Book Now, Pay Later vacations. No need to save up or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up travel deals while they last.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.