32+ Vacation Rentals Near Chatham Vineyards |
  1. USA
  2. Virginia
  3. Machipongo
  4. Chatham Vineyards

Stayifyoudare - Vacation Rentals in Chatham Vineyards

Property Image From $248
         

10.0 (74 Reviews)
Cottage
SANDY HILL SUNSETS
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $98
         

|
10.0 (1 Review)
Apartment
Indigo Studio Loft
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $325
         

9.0 (3 Reviews)
House
271 m² House ∙ 4 bedrooms ∙ 10 guests
  • 2917 ft² House
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $91
         

6.0 (234 Reviews)
Hotel
Budget Inn By OYO Nassawadox Hwy 13
  • TV
  • Bedding/Linens
  • Wellness Facilities

View Availability
Property Image From $234
         

10.0 (158 Reviews)
Apartment
Thelma’s Dawn Getaway! A true No Drama Zone
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $956
         

|
New
House
Stunning Chesapeake Bay Farmhouse with Dock and Kayaks
  • Parking
  • Accessibility
  • Security/Safety

View Availability
Property Image From $229
         

10.0 (58 Reviews)
House
Nassawadox Creek Waterfront Home with Private Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $346
         

10.0 (13 Reviews)
House
Private Country Beach Retreat
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $430
         

10.0 (6 Reviews)
House
Stunning Chesapeake Bay Farmhouse w/Dock & Kayaks
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $393
         

10.0 (6 Reviews)
House
Waterfront family home with great views, full kitchen, & strong Wi-Fi.
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $695
         

10.0 (4 Reviews)
House
Waterfront, Gorgeous 4 BDR, 3 BA Beautiful views & sunsets
  • Air Conditioner
  • Parking
  • View

View Availability
Property Image From $771
         

10.0 (3 Reviews)
House
Exquisite 4 bedroom, 3 and a half bath Georgian Estate Home on the Beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $925
         

9.8 (36 Reviews)
House
Luxury Beachfront 5 Bedroom, 3.5 Bath home with 200 ft. of PRIVATE BEACH!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $157
         

9.8 (29 Reviews)
Cottage
Relax and Renew on your private deck overlooking the Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $89
         

9.8 (14 Reviews)
Apartment
Indigo Studio Loft
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image
New
From $448
         

New
House
Charming Waterfront Retreat with Private Dock
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $352
         

New
Cottage
The Waverly Tree House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

View Availability
Property Image From $302
         

New
House
Chesapeake Bay Escape
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $32
         

New
House
Chesapeake Retreat
  • Air Conditioner
  • Pet Friendly
  • Child Friendly

View Availability
Property Image From $389
         

10.0 (90 Reviews)
Cottage
Feed Your Soul at Silver Beach Cove
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $201
         

9.8 (71 Reviews)
Cottage
Share Splendid Sunsets Over the Beautiful Chesapeake Bay!
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $164
         

10.0 (41 Reviews)
Cottage
Chesapeake Bay Beach Cottage,private beach book Fall now!
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $300
         

10.0 (34 Reviews)
House
Historic Waterfront Home With Big Views Of The Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $378
         

10.0 (3 Reviews)
House
Brand-new waterfront house on the Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

View Availability
★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chatham Vineyards.

Weather in Chatham Vineyards

View the weather forecast for Chatham Vineyards before booking your Chatham Vineyards Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chatham Vineyards, VA

Stayifyoudare offers a large selection of top attractions around Chatham Vineyards. Research things to do on your vacation before you visit Chatham Vineyards.


Cape Charles Beach Chesapeake Bay Bridge-Tunnel Barrier Islands Center Kiptopeke State Park Deltaville Marina Eastern Shore of Virginia National Wildlife Refuge Bloxom Winery Bay Creek Golf Club Northampton Shopping Center Eastern Shore Railway Museum Deltaville Maritime Museum White Stone Beach Barrier Island Museum Eyre Hall Holly Point Nature Park North Street Playhouse Holly Grove Vineyards Cape Charles Museum & Welcome Center Bethel Beach Kegotank Bay