Short-Term Rentals in Chatham Vineyards, VA: Compare 10+ Sites & Save

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  3.  USA

  4.  Virginia

  5.  Machipongo

  6.  Chatham Vineyards

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21 Best Short-Term Rentals in Chatham Vineyards (Starting from $31)

Stunning Chesapeake Bay Farmhouse with Dock and Kayaks
Stunning Chesapeake Bay Farmhouse with Dock and Kayaks
House
Nassawadox, VA, USA
3.0k from Chatham Vineyards center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms10 Guests
New to Booking
$956
Average price / night
Check Availability
Historic Waterfront Home With Big Views Of The Chesapeake Bay
Historic Waterfront Home With Big Views Of The Chesapeake Bay
House
Franktown, VA, 23354, United States
2.6k from Chatham Vineyards center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

35 reviews

$318
Average price / night
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Indigo Studio Loft
Indigo Studio Loft
Apartment
Chatham Vineyards, Machipongo, Virginia, USA
7.0k from Chatham Vineyards center

Breakfast, Internet, Balcony/Terrace, Air Conditioner, Parking, Pet Friendly, Child Friendly

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$98
Average price / night
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The Waverly Tree House
The Waverly Tree House
Cottage
Machipongo, VA, 23405, United States
2.9k from Chatham Vineyards center

AC, Heater, Internet, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$380
Average price / night
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Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
House
Machipongo, VA, 23405, United States
3.0k from Chatham Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$626
Average price / night
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Nassawadox Creek Waterfront Home with Private Pool
Nassawadox Creek Waterfront Home with Private Pool
House
Exmore, VA, 23350, United States
3.3k from Chatham Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

63 reviews

$349
Average price / night
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Private Country Beach Retreat
Private Country Beach Retreat
House
Machipongo, VA, 23405, United States
3.5k from Chatham Vineyards center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

15 reviews

$532
Average price / night
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Feed Your Soul at Silver Beach Cove
Feed Your Soul at Silver Beach Cove
Cottage
Exmore, VA, 23350, United States
3.7k from Chatham Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

92 reviews

$432
Average price / night
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Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore
Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore
House
Exmore, VA, 23350, United States
3.9k from Chatham Vineyards center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$350
Average price / night
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Peaceful, Pet-Friendly Escape with Waterfront Sunsets & Private Dock (No Fees!)
Peaceful, Pet-Friendly Escape with Waterfront Sunsets & Private Dock (No Fees!)
Cottage
Jamesville, VA, 23398, United States
4.1k from Chatham Vineyards center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

53 reviews

$469
Average price / night
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Share Splendid Sunsets Over the Beautiful Chesapeake Bay!
Share Splendid Sunsets Over the Beautiful Chesapeake Bay!
Cottage
Exmore, VA, 23350, United States
4.2k from Chatham Vineyards center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
9.6

Exceptional

73 reviews

$214
Average price / night
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Chesapeake Bay Escape
Chesapeake Bay Escape
House
Exmore, VA, 23350, United States
4.3k from Chatham Vineyards center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$283
Average price / night
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Relax and Renew on your private deck overlooking the Chesapeake Bay
Relax and Renew on your private deck overlooking the Chesapeake Bay
Cottage
Silver Beach, VA, 23350, United States
4.4k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

29 reviews

$157
Average price / night
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Chesapeake Bay Beach Cottage Private Silver Sandy Beach
Chesapeake Bay Beach Cottage Private Silver Sandy Beach
Cottage
Exmore, VA, 23350, United States
4.6k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$209
Average price / night
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 Thelma’s Dawn Getaway! A true No Drama Zone
Thelma’s Dawn Getaway! A true No Drama Zone
Apartment
Exmore, VA, 23350, United States
4.8k from Chatham Vineyards center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

158 reviews

$233
Average price / night
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SANDY HILL SUNSETS
SANDY HILL SUNSETS
Cottage
Exmore, VA, 23350, United States
4.8k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

74 reviews

$247
Average price / night
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Franktown Artist Cottage
Franktown Artist Cottage
House
Franktown, VA, 23354, United States
5.3k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
8.4

Very Good

25 reviews

$104
Average price / night
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Luxury Beachfront  5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!
Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!
House
Jamesville, VA, 23398, United States
5.9k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Microwave, No Smoking, Toys

5 Bedrooms12 Guests
9.8

Exceptional

36 reviews

$946
Average price / night
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Chesapeake Retreat
Chesapeake Retreat
House
Exmore, VA, 23350, United States
6.5k from Chatham Vineyards center

AC, Patio

1 Bedroom2 Guests
New to Booking
$31
Average price / night
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Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets
Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets
House
Jamesville, VA, 23398, United States
6.6k from Chatham Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave

4 Bedrooms13 Guests
10.0

Exceptional

4 reviews

$708
Average price / night
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Dreamers Bay
Dreamers Bay
House
Jamesville, VA, 23398, United States
6.9k from Chatham Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$509
Average price / night
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Other accommodation types in Chatham Vineyards:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Chatham Vineyards.

Chatham Vineyards Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 21 verified short-term rentals in Chatham Vineyards, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chatham Vineyards vary depending on location, property size, and travel dates. Rates typically start from around $31 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chatham Vineyards include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chatham Vineyards, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chatham Vineyards often include amenities such as Fireplace/Heating, Bedding/Linens, and Kitchen, providing a comfortable and convenient stay.

Short-term rentals in Chatham Vineyards are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.