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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Property grounds

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

10.0 out of 10, Exceptional, (201)
"The cottage is extremely well appointed, very clean, comfortable and affords a great view of Hills Bay. Three adults and a toddler enjoyed their 3-night stay immensely. ."
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Modern Beachfront Cottage with Endless Bay Views
Outdoor dining

Modern Beachfront Cottage with Endless Bay Views

9.8 out of 10, Exceptional, (67)
"I needed a quick break from work and this was the perfect place! "
Modern Beachfront Cottage with Endless Bay Views
3 BR Bay Home w Private Dock & all the Amenities
Property grounds

3 BR Bay Home w Private Dock & all the Amenities

10.0 out of 10, Exceptional, (10)
"We wanted a place to get away with our kids before the hustle and bustle of the school year and sports start. It was a perfect home with lots of great amenities and a great location!"
The price is SARĀ 1,219
SARĀ 2,813 total
includes taxes & fees
4 May - 5 May
3 BR Bay Home w Private Dock & all the Amenities
Virginia Retreat w/ Porch & Grill, Near Beaches!
Interior

Virginia Retreat w/ Porch & Grill, Near Beaches!

3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!
*SANDY HILL SUNSETS*
On the beach, sun loungers

*SANDY HILL SUNSETS*

10.0 out of 10, Exceptional, (72)
"Wonderful trip as always!"
*SANDY HILL SUNSETS*
Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!
Property grounds

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
Exterior

ESVA Down by the Sea & Pet Friendly

9.6 out of 10, Exceptional, (4)
"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.
Beach/ocean view

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

9.6 out of 10, Exceptional, (88)
"We have stayed here multiple times and have loved our stay. Clean and cozy. Always feels like home. Owner has very good communication. "
Kiptopeke Drive Cozy Cottage Right Up The Road From Kiptopeke State Park.
Cute Cottage Awaits You! First Floor Primary Bedroom
Fridge, microwave, oven, stovetop

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
Property grounds

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
Terrace/patio

Relax and Renew on your private deck overlooking the Chesapeake Bay

9.8 out of 10, Exceptional, (25)
"Beautiful views and sunsets. So relaxing"
Relax and Renew on your private deck overlooking the Chesapeake Bay
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Property grounds

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

10.0 out of 10, Exceptional, (5)
"The place is amazing. The pictures on the site do not do the property justice as it is absolutely amazing. Canā€™t wait to stay there again."
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
'Cora's Cottage' Near Chesapeake Bay Access!
Beach

'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
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
Terrace/patio

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!
House (3 Bedrooms) | Interior

Charming Cape Charles Vacation Rental Home!

3.0 star property
Charming Cape Charles Vacation Rental Home!
Scenic Port Haywood Gem w/ Waterfront Views!
House (3 Bedrooms) | Interior

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!
TV, fireplace

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
Outdoor dining

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
Property grounds

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
Interior

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
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach
3 bedrooms, iron/ironing board, WiFi, bed sheets

Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach

9.6 out of 10, Exceptional, (124)
"Location in everything and Cape Cottage is in perfect location. Quaint 1901 house that has turn of the century charm and modern convenience."
Downtown, Sleeps 9, Dog-friendly, Short Walk to the Beach
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex
Exterior detail

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

9.8 out of 10, Exceptional, (80)
"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
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.