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Compare 41 Cottages in Machipongo with updated reviews, rates, and availability.

Gwynn's Island Cottage: Waterfront w Private Beach, Sunsets over Water

10.0 out of 10, Exceptional, (200)
"My daughter's and I had a wonderful stay at the cottage! It has everything you need andwithin 30/40 min drive from various little towns and beaches. "
Gwynn's Island Cottage: Waterfront w Private Beach, Sunsets over Water

Modern Beachfront Cottage with Endless Bay Views

9.8 out of 10, Exceptional, (66)
"Stayed for 3 days- the views were absolutely amazing (sunrise and sunset). All the neighbors we very friendly. Town was a short drive away with some great food. Will absolutely be returning."
Modern Beachfront Cottage with Endless Bay Views

3 BR Bay Home w Private Dock & all the Amenities

10.0 out of 10, Exceptional, (10)
"My family and I have stayed at countless properties over the years through VRBO. As a family of five (5), including two teens, and an 8-year-old, one can imagine the difficulties associated with finding a vacation rental that had something that tickled the fancy of each. We’ve been very happy with the properties and the accuracy of the listings. There has never been an occasion where any of us felt deceived or that the property failed to meet expectations. With that said, our recent stay at this...
The price is AED 1,194
AED 2,743 total
includes taxes & fees
20 Apr - 21 Apr
3 BR Bay Home w Private Dock & all the Amenities

Virginia Retreat w/ Porch & Grill, Near Beaches!

3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!

*SANDY HILL SUNSETS*

10.0 out of 10, Exceptional, (71)
"From start to finish, Christie was warm, friendly and welcoming. The hospitality and communication were off the charts. The private beach view is one of the most amazing views we experienced. Very private and a long stretch of beach to walk along. The place was clean and has everything you need from a basics standpoint. The surroundings were awesome. Lots of fields and nature to explore nearby with the golf cart. Highly recommend and will be back."
*SANDY HILL SUNSETS*

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!

ESVA Down by the Sea & Pet Friendly

9.4 out of 10, Exceptional, (3)
"My work team stayed here while on a project for Eastern Shore. It is a good location for our project. GPS did led us to the wrong location, but the homeowner helped. The house was clean, and the beds were comfortable. "
ESVA Down by the Sea & Pet Friendly

Kiptopeke Drive Cozy Cottage Right Up The Road From Kiptopeke State Park.

9.6 out of 10, Exceptional, (88)
"We enjoy the area and boating in the bay and on the ocean side. The restaurants are good and we generally take a day down at Virginia Beach/Back Bay and a day up at Chincoteague/Assateague. They week we managed four solid days on the water. "
Kiptopeke Drive Cozy Cottage Right Up The Road From Kiptopeke State Park.

Cute Cottage Awaits You! First Floor Primary Bedroom

3.0 star property
Cute Cottage Awaits You! First Floor Primary Bedroom

Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia

10.0 out of 10, Exceptional, (50)
"Totally enjoyed our stay. Very relaxing, very comfortable!"
Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia

Relax and Renew on your private deck overlooking the Chesapeake Bay

9.8 out of 10, Exceptional, (25)
"We had such a wonderful and relaxing week here! We loved the private waterfront deck - from our morning coffee to evening sunsets (which were stunning!) we spent most of our time there. The cottage was inviting and clean with nice beach decor and a very well-equipped kitchen and the cottage had just about anything you could need. Donna was a very responsive and accommodating host who met us and showed us around. She’s great! The only negatives we would have - and this is only because we are a...
Relax and Renew on your private deck overlooking the Chesapeake Bay

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (5)
"Very nice property, we made good use of the dock and were able to launch my 18.5 ft boat from the concrete ramp. Fishing, crabbing, boating were good (though crabs a bit on small side) the cottage was clean, well organized and neat. Everything was really nice and Genevieve was extremely responsive and pleasant to deal with."
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

'Cora's Cottage' Near Chesapeake Bay Access!

10.0 out of 10, Exceptional, (2)
"House was very clean and comfortable. Great spot for a family with young adults. Nice bike ride or walk to the beautiful water area. "
'Cora's Cottage' Near Chesapeake Bay Access!

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

3.0 star property
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Updated Cape Charles Home ~ 2 Mi to Beachfront!

3.0 star property
Updated Cape Charles Home ~ 2 Mi to Beachfront!

Charming Cape Charles Vacation Rental Home!

3.0 star property
Charming Cape Charles Vacation Rental Home!

Scenic Port Haywood Gem w/ Waterfront Views!

3.0 star property
Scenic Port Haywood Gem w/ Waterfront Views!

Cape Charles Home: 4 Mi to Kiptopeke State Park!

3.0 star property
Cape Charles Home: 4 Mi to Kiptopeke State Park!

Charming Painter Home w/ Chesapeake Bay Views

3.0 star property
8.0 out of 10, Very Good, (1)
Charming Painter Home w/ Chesapeake Bay Views

The Waverly Tree House

The Waverly Tree House
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 property types in Machipongo

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

10.0 out of 10, Exceptional, (4)
"We had a great time and stay at this property!! Would love to stay here again!"
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

9.8 out of 10, Exceptional, (79)
"Wonderful location & House for a family holiday stay! I loved being across the street from the park and close to the beach. Will stay here again!"
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

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

9.6 out of 10, Exceptional, (131)
"We planned a quick get-a-way and decided to come to Cape Charles to spend the day and stay over night. The house was charming with plenty of room. The owners communicated well and they were very accommodating on my last minute trip planning. The beach wasn’t far at all and town was in walking distance with nice weather. We came in March so it wasn’t perfect beach weather but we are hoping to come back when it’s warmer! "
The price is AED 716
AED 1,784 total
includes taxes & fees
16 Apr - 17 Apr
Bay cottage, Beach 100 yards away! RESERVE NOW!!!
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.