Chatham Vineyards

  • A local lure for wine connoisseurs and vacationeers alike, Chatham Vineyard's lush vines and historic buildings draw interest.

    A local lure for wine connoisseurs and vacationeers alike, Chatham Vineyard’s lush vines and historic buildings draw interest.

Nearby Rentals

–  Chatham Vineyards

A local lure for wine connoisseurs and vacationeers alike, Chatham Vineyard

Chatham Vineyards

Nestled on Virginia’s eastern shore, a historic working farm dating back four centuries, Chatham Vineyards grow quality grapes for use in fine wines. Come visit them at special events held in their winery and at festivals around Virginia!
1 – Luxury Craftsman Cottage-Sleeps 6, Only 500 Feet To Beach – 15 Miles

Luxury Craftsman Cottage-Sleeps 6, Only 500 Feet To Beach

“Built with character” this mission-style cottage is actually under 15 years old yet looks like its been here for a century. One block from the beach in the serene Chesapeake Bay town of Cape Charles. Step back in time to a Mayberry-like atmosphere in a pristine cottage with all new furnishings. This home was built to seamlessly fit in to the turn of the century architectural style of the town, and is furnished with a beachy restoration theme in mind. If you want a fully-stocked rental located one block from town and one block from the beach, this home is for you! Perfect for a family, couples (golfers will enjoy nearby Bay Creek!) and girls weekends! A luxury property.

2 – Park Place – Comfy Condo Close to Beach – 20 Miles

Spacious Living Room and DIning Area

Park Place – Comfy Condo Close to Beach

Located a walk away from Kiptopeke State Park, 7 miles from the Historic Town of Cape Charles and 3 miles from one of the Modern Wonders of the World, The Chesapeake Bay Bridge Tunnel, Park Place offers the comforts of home and the location for easy day trips to Virginia Beach, Williamsburg, and Chincoteague.  Park Place has been recently renovated by the new owners and shows pride of ownership. The Living Room easily seats 6 and all can watch the large flat screened TV offering a cable package including MLB. The dining Area is spacious with seating for 6 and the fully equipped kitchen finishes out the open concept living area so you’re never cut off from the rest of the family.

There are 2 first floor bedrooms and 1 full bath which makes it convenient for the elderly or small children to maneuver.

Upstairs is the ultimate Master Bedroom Suite offering a king size bed, mater bathroom with jetted tub, separate shower and dual sinks. A private balcony awaits you.

With close access to Cape Charles, you have a wonderful public beach, restaurants, shopping, jet ski rentals, theatre, library, ice cream shop, gourmet food stores and specialty shops. Artists abound on the shore and their work is amazing.

 

3 – Laughing Gull-PET FRIENDLY Sleeps 6-8 One and one half blocks to Beach – 15 Miles

Living Room with Flat Screen TV and DVD player

Laughing Gull-PET FRIENDLY Sleeps 6-8 One and one half blocks to Beach

Located one block to the beach and right in the center of town. Leave your car and walk to shopping, restaurants, beach and fishing pier. Located on the second floor (elevator building), this Condo has everything you will need for the vacation you have been waiting for. Offering 2 bedrooms and 2 full baths, the home sleeps 6 to 8 comfortably. The Master Bedroom has a Queen size bed and the second bedrooms offers 2 sets of bunk beds. The living room offers a Queen size sleeper sofa.

Enjoy the fully equipped kitchen just in case you want to cook. The Dining Room seats 6 comfortably.

The cozy living room offers a DVD player and  flat screened TV. Access to the back deck is off the Living Room.

The Condo has access to the REAR rooftop deck offering town views. Walk 1 and 1/2 blocks to the beach to watch the sunset and celebrate the end of the day.

Conveniently located for day trips to Chincoteague, Virginia Beach and Williamsburg. Brochures will be available in the Condo to help you decide what to do each day.

THIS HOME HAS A LIMIT OF 1 DOG

4 – Bay Dunes – PLAN YOUR FALL GETAWAY-FALL RATES WITH SUMMER WEATHER!! – 20 Miles

Steps away from private beach access

Bay Dunes – PLAN YOUR FALL GETAWAY-FALL RATES WITH SUMMER WEATHER!!

Plenty of room and privacy in this extra-large luxury home in the desirable Bay Ridge community, steps from the best private beach on the Eastern Shore.

  • Five bedrooms, each with private full bath and flat screen TV
  • Den with queen sofa bed and large flat-screen TV
  • Spacious family entertainment area
  • Open gourmet kitchen with large island, breakfast bar, 2 dishwashers and 2 ovens
  • Dining room with large dining table
  • Powder room
  • Two expansive decks w/deck furniture
  • Screened in porch
  • Beautiful wooded lot with Chesapeake Bay views
  • Two outdoor showers with dressing rooms
  • Enjoy the Bay Ridge community, with private pool, covered picnic area and tennis courts.

 

Most of our properties have 4 to 7 night minimums stays during peak season (June 18 to September 9). If you have a special need, don’t hesitate to contact us. 

This beachfront home is waiting for a large family to enjoy the 5 bedrooms plus Den, 5.5 bathrooms, spacious entertaining area and a large gourmet kitchen. In addition, enjoy the expansive decks and screened in porch with views to the Bay. Walk to the end of the driveway and see the boardwalk leading to the communities private beach. Walk to the end of the block and enjoy the community pool. Take advantage of 2 convenient outdoor enclosed showers to shake the sand or chlorine off before entering the home.

5 – Pelican Watch – 1 Block to Beach, Kayak Included PET FRIENDLY – 15 Miles

ONE BLOCK TO BEACH,  BAY VIEWS, KAYAK INCLUDED

Pelican Watch – 1 Block to Beach, Kayak Included PET FRIENDLY

This is a charming 1000 sq ft cottage with bay breezes. You are a 600 foot walk to the bay beach and a few blocks to the restaurants, shops, harbor, fishing pier, theater and marina. This is the quiet end of town and the yard is fenced in so pets are considered. 3 bedrooms, 1 downstairs with queen bed, 2 upstairs bedrooms, one with two twin beds and the other with one twin bed. 1 bathroom downstairs with tub/shower combo. Comfortable airy living room. Small well-equipped kitchen and separate dining room. Utility room with washer/dryer.

The steps to the second floor are on the steep side. Elderly or very small children should be monitored.

Gas grill and 2 person kayak in yard. Wifi Internet/DishTV/DVD/CD. Romantic, cozy and clean. On street parking for car and boat. Charter a fishing boat or walk to the pier and fish for free. Sunsets are spectacular down on the beach. The house is on the north end of the beach, and we love watching the seagulls and pelicans and other shore birds perching on the pilings from the old ferry dock.

6 – AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1 Block to Town – 15 Miles

Victorian Beach House 2 Blocks to the Beach

AT LAST Cottage-PET FRIENDLY-Sleeps 6, Two Blocks To Beach, 1 Block to Town

AT LAST is the perfect name for this Victorian Beach House. The owners have lovingly brought the home back to life and now want to share it with you. This PET FRIENDLY home is 2 blocks to the Beach, 1 block to Town and 2 blocks to the 5 acre Town Park. Park your car for the week and explore the Town on foot or in a rented golf cart. Cape Charles is golf cart friendly.

The home offers 3 bedrooms, 2 full baths, living room, dining room, family room, kitchen and laundry room. A large fenced in back yard with mature growth trees and plantings offer a cozy setting as your sitting around the fire-pit.

Cape Charles offers great restaurants, shopping, gourmet markets, art galleries, theater, pharmacy, medical services and library. No license is required for the Town fishing pier so bring your polls.

Do you like horseback riding, antiquing, fishing, sailing, jet skiing, kayaking, windsurfing?. We have all that and more. Bring your family on a vacation they will remember. We know you’ll be back.

7 – Life’s A Beach – 15 Miles

 Lifes A Beach Front View

Life’s A Beach

Able to sleep 15 in beds, this home works great for family reunions or for a multi-family get together.
With bedrooms on the 2nd and 3rd floors, there is plenty of room to spread out so everyone can enjoy the place without crowding. There is cable TV in the family room and three bedrooms, a blue-ray player in the family room, and a DVD player in bedroom 4. Bedroom combinations: Bedroom 1 – King, Bedroom 2 – 1 twin trundle and 1 bunk bed (full on the bottom, twin on the top), Bedroom 3 – 1 Full, Bedroom 4 – 1 full and 1 bunk bed (full on the bottom, twin on top). Bedroom 5 – 1 queen.

Located only one block from the main street with its shops and eateries there are now a great new pizza place and Brown Dog Ice Cream (ranked among the top ten in the country by Trip Adviser). This is a golf cart friendly town and carts are available for rent at several places as well as beach cruiser bikes. Day trips to Chincoteague and Virginia Beach and even Williamsburg are all doable.

Visit Cape Charles, stay at Life’s A Beach and experience one of the best vacations you can have.

8 – Indigo Cottage – 2 Blocks To The Beach, Rent One Or Both Sides. – 15 Miles

Indigo Cottage – 2 Blocks To The Beach, Rent One Or Both Sides.

Newly renovated with all new kitchen and baths. Only two blocks to the town beach and a little over 1 block to the town park, this new listing is beautifully furnished. In addition to the attention to interior details, there is a big gas grill and picnic table in the back yard  as well as an outdoor shower.

There is a bedroom with a king bed, one with a queen bed and a third bedroom the has a bunk bed plus a twin bed and a TV for the kids.

Only 4 blocks to the main street with shops and eateries, it is an easy walk or you can rent a golf cart to get around town (they’re legal in Cape Charles)

The very kid friendly beach is never overcrowded like many east coast beaches so it makes for a relaxing time. Bike rentals are also available and if you happen to have a trailerable boat, there are great launch ramps at the town harbor and plenty of transient docking. 

9 – Sunset Bay – 15 Miles

Welcome to Sunset Bay

Sunset Bay

Our newest vacation rental with amazing views of the Chesapeake Bay. Enter the spacious foyer and up one flight to an incredible open concept Living Room, Dining Area and Large Kitchen with all the bells and whistles. The living room is spacious with wraparound couch and lounge chairs facing the large screen TV and fireplace. Looking west out the sliding glass doors is a full balcony and an enclosed screened in porch looking out over the Bay and beach. 

The Dining Area can seat 10 and the Breakfast Bar an additional 2 guests.

The kitchen is fully equipped and offers dishwasher, disposal, microwave, wall oven, cook top, serving dishes, pots, pans, utensils

There are 2 downstairs bedrooms. The master with master bath and a second bedroom with access to its own bathroom.

On the main level a third bedroom offering bunk beds. A single upper and a double lower. The den offers a queen sleeper sofa.

The third level offers amazing views as well as a balcony to relax and enjoy the sunsets. A wet bar and a mini fridge complete the loft.

The home is located in the Historic town of Cape Charles in the resort community of Bay-Creek.

This home enjoys access to a community pool and tennis court, two signature golf courses (fee charged), private beach as well as the town beach.

Plenty of shopping, restaurants, fishing, kayaking, eco tours, antiquing, horseback riding, jet skiing, bird watching, 

Cape Charles is poised for great day trips to Chincoteague, Virginia Beach, Williamsburg and Busch Gardens.

We require a minimum stay of 3 nights over Memorial Day and Labor Day weekend.

 

10 – Dryden House-Beachfront Historic Home w/ AMAZING WATER VIEWS – 15 Miles

Front View

Dryden House-Beachfront Historic Home w/ AMAZING WATER VIEWS

The Dryden House is offered as a weekly private rental after an extensive 18 month historical renovation. Enjoy all of the historical charm and updated amenities that this grand home has to offer. You can step back in time and step off your porch into the dunes of the Chesapeake Bay.

This 1912 historic private home known as the Dryden House is located within a registered historic district, known as the Sea Cottage Addition of Cape Charles, which is comprised of an intact grouping of architecturally significant commercial and residential buildings constructed between 1850 and 1915 that display a variety of styles and types of architectural ornamentation popular during this era. The Dryden House is unique due to its prominent size and central location upon Bay Avenue just steps from the beach and only two blocks from the town’s charming business district.

This three-story Victorian has an extensive wrap around porch, with a porte cochere and was constructed by E. T Dryden who built other notable homes nearby. This beachfront home features Bay views from almost every room in the home including all second floor bedrooms with a water view. There are two full baths on the second floor and a full bath on the first floor with a convenient washer and dryer. Before you come into the home from the beach, you can wash away the salt and sand in the outdoor shower.

The large kitchen has new high end appliances, with two full size sinks spacious enough for two chefs and a separate beverage center and coffee station assuring you will not be bumping elbows with your guests! The oversized dining room features an expandable dining table that can easily seat 12 plus for meals. Formal paneled pocket doors make this floor plan as open or private as you desire. 

Finished third floor family room with large flat screen TV, DVD, soundbar, Netflix and Amazon Prie. Wii with balance board and a good selection of Wii games. A selection of over 50 movies for both kids and adults. A full size foosball table completes the game room for when your’re feeling competitive. There is three zone air-conditioning to keep you comfortabel on those hot days and nights.

The town gazebo and free fishing pier is to the left of the home and the extensive town walkways make this ideal for strolling or catching an evening horse and carriage ride on the Bay. Sunsets are nightly!

PETS WILL BE CONSIDERED ON A CASE BY CASE BASIS.

IF ALLOWED, THE NON-REFUNDABLE PET FEE IS $260.00

WEEKLY RENTALS ONLY DURING PEAK SEASON.
 
 
 
  

Map

Nestled on Virginia’s eastern shore, a historic working farm dating back four centuries, Chatham Vineyards grow quality grapes for use in fine wines. Come visit them at special events held in their winery and at festivals around Virginia!

Details


Category:
Winery
Address:
9232 Chatham Rd
Machipongo, Virginia 23405-2727
Phone:
757-678-5588
Web Address:
http://www.chathamvineyards.net/