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Historic Waterfront 'Oakland' off Chesapeake Bay, Dock, Pets Welcome

Owner - Cathleen

Member since: 2010
Speaks English
Bedrooms 6
Separate WC's1
Property type house
Minimum Stay 2 - 7 nights

Owner - Cathleen

Member since: 2010
Speaks English
Response time:
Within a few days
Response rate:
Calendar last updated:
20 May, 2015
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Trust & Security
Free protection up to £700 for all bookings.
£10,000 fraud protection when you pay using the secure HomeAway Payments system. 
Low cost, tailor-made insurance exclusively for holiday rentals from Europ Assistance. Get a quote

Historic Waterfront 'Oakland' off Chesapeake Bay, Dock, Pets Welcome

Bedrooms 6
Separate WC's1
Property type house
Minimum Stay 2 - 7 nights


Photos and Description of this 6 bedroom holiday home in Mathews - Oakland - Circa 1840

6 Bedrooms, 4.5 Bath, Deepwater Dock, Koi Pond, WiFi CableTV HBO

Set in rural Mathews County, historic Oakland is located on one of the country's many tidal waterways connected to Mobjack or Chesapeake Bays. Situated on a point of land, it has sweeping views on to Oakland Creek, Blackwater Creek and the North River - with easy quick access to Mobjack and the Chesapeake Bay. It is spacious and sleeps 12-13 comfortably.

Mathews is peaceful and serene yet easily accessible from major population centers. It is less than an hour away from all of the Williamsburg attractions (Busch Gardens, Water Country, Jamestown, Yorktown, William and Mary, the Williamsburg Pottery & Prime Outlets). Mathews has 5 public beaches, a lighthouse (the 3rd oldest in the Bay), and a quaint downtown. There are also many outdoor options to supplement any vacation.

Oakland, built in 1840, is full of charm. We've endeavored to keep as many of the original architectural features in place as possible (pull chain toilet, claw foot tub and old door knobs and locks for example) while making it clean, comfortable, well equipped and welcoming to all who visit.

History buffs will enjoy looking for the names, dates and initials etched in the brick chimney in the den and on the original glass window panes (Jane Byrd January 1, 1871 is one example found in the living room). Furnishings and decor have been carefully selected to be comfortable and family friendly. Toys, books, games and outdoor activities are abundant. The outdoor shower with hot and cold water (added Summer 2013) has been a great addition and solves the problem of cleaning off muddy little feet (human and canine) that have been tramping around the shoreline looking for treasures.

Oakland has 6 bedrooms all of which are located on the 2nd floor (K, Q, twin bunks, twin with trundle,2 twins, twin) and it sleeps 11 comfortably. There is also a pull out sofa on the first floor (full size) that can accommodate 2 more guests. There are 4.5 baths, a well equipped kitchen (updated in 2013) - plus a summer kitchen with laundry facilities and a spare fridge and freezer for bait/seafood or kitchen fridge overflow, screened porches and dining area, formal dining and living rooms, plus a spacious den with a flat screen TV, DVD, Wii and computer with internet and Wi-Fi.

Relax with a glass of wine on the dock and watch the sunset, take a dip in the river-front pool (open Memorial Day through Labor Day), fish from the shoreline, hunt for oysters (which are plentiful) at low tide, drop the crab pots in -- or head out in the canoe or sunfish sailboat and explore the tributaries. Children of all ages will enjoy feeding the koi in the decorative pond adjacent to the house (complete with fountain and lily pads!) and will relish running around at night catching lightening bugs on the large lawn. There is also a swing set, slide and sandbox.

If you have a boat, launch from the deep water dock which can accommodate boats of fairly good size. Mobjack Marina is across the creek and is a good place to launch or fuel up. Jet skis (which can be rented locally) are a blast as well. In the evening, enjoy grilling out by the pool or gather around the chiminea and enjoy the nighttime sky. For a real treat, take the family to “Donk’s” (Virginia’s ‘Lil Ol Opry which is situated in a historic old theater) for some live entertainment and a real taste of the local culture.

Special Note: Edgar Allen Poe fans will appreciate the fact that Edgar's sister Rosalie Poe often visited the house (which was owned by Poe family cousins). The Mathews County Historical Society archives contain a letter she wrote that references her time at Oakland.

Oakland is a short drive from Mathews' five public beaches and is less than 15 minutes to the grocery store, ABC store and local restaurants, antique stores and area entertainment. The North Star Market is very nearby and sells basic groceries, bait and gasoline. Downtown Mathews has many shops but it’s larger neighbor Gloucester is 15 minutes away and has larger chain stores and restaurants (Walmart and Home Depot + Ruby Tuesdays and Applebee's + Sweet Frogs for example).


Mathews County is located in the Chesapeake Bay region of Virginia, on the eastern tip of the Middle Peninsula. The second smallest county in Virginia, Mathews features more than 200 miles of shoreline! It is bordered by the Chesapeake Bay, Mobjack Bay and the Piankatank River. One of the highlights of Mathews County is the New Point Comfort Lighthouse, which marks the entrance to Mobjack Bay. The Narrows Marina on Gwynn's Island offers watersports, and four other marinas are in the community.

There are an abundance of colonial and Civil War sites to explore. Mathews Court House Square is a collection of 18-century and 19th-century buildings along with an active historical society. Its close proximity to Virginia's Historic Triangle -- Jamestown, Williamsburg and Yorktown -- offers addition incentive to visit this coastal community.

Visitors can take advantage of numerous self-guided trails as well as enjoy experienced trail guides on the county's birding, bicycling and driving tours.

More Details
  • Events Allowed
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • pets considered
  • wheelchair inaccessible
Owner - Cathleen (Owner)
Member since: 2010
Speaks English
Response time:
Within a few days
Response rate:
Calendar last updated:
20 May, 2015

About Owner - Cathleen

Our family resides nearby but we decided to purchase Oakland as soon a we saw it. It has tremendous appeal for us and we always hate when it is time to pack up and return to work and school. Oakland is new to the rental market (September 2013) and we are looking forward to sharing this special home with others.

Owner - Cathleen purchased this house in 2010

Why Owner - Cathleen chose Mathews

This property has a beautiful view and Mathews reminds me of how Virginia was when I was growing up. Our children and pets love the outdoors and run free without concern of traffic or unwelcome visitors. Mathews locals really could not be more friendly and there is a sense of caring in the community and a respect for the Bay that one does not find elsewhere.

What makes this house unique

Private and affordable, yet an easy commute to all Williamsburg activities and even more distant sites like Norfolk, Richmond, Washington DC and Baltimore.

Why HomeAway

Bedrooms 6
Separate WC's1
Property type house
Minimum Stay 2 - 7 nights
Book with confidence
Book with confidence
Guaranteed, secure, with no booking fees
Trust & Security
Free protection up to £700 for all bookings.
£10,000 fraud protection when you pay using the secure HomeAway Payments system. 
Low cost, tailor-made insurance exclusively for holiday rentals from Europ Assistance. Get a quote


based on 13 holidaymaker reviews

Write a Review
Historic Waterfront 'Oakland' off Chesapeake Bay, Dock, Pets Welcome
average rating of 5.0 based on 13 reviews

Doing Mathews in Style

  • 5 of 5

My wife and I, including three other couples, rented Oakland for three days. We all had a delightful stay. The property is old, and needs some work - but then again, that is part of its charm. It is not a 21st century chateau; it is a wonderful, lingering momento of the antebellum era.

The rooms were more than adequate for four couples - and each couple had their own own bathroom. The kitchen is somewhat short on counter space, but it is well equipped and we managed just fine. We cooked, dined and enjoyed every minute. The common living quarters are spacious and comfortable - but we spent our time outdoors, so we did not have a chance to use them seriously.

One of our goals in staying at Oakland was to access the river and bay with our kayaks. We were not disappointed. There is excellent access to the water directly from the property. There is also a pool, but we visited in May and the pool was not yet functioning. Nonetheless, we had wine and cheese every evening on the deck surrounding the pool - not a bad substitute for the pool.

Oakland is also well located relative to historic sites such as Yorktown (which we visited) and Mathews, where there are a couple superb restaurants.

We commend Oakland to anyone contemplating a few days of relaxation in a mansion straight out of southern history but sufficiently outfitted with modern conveniences to guarantee an excellent vacation.

  • Review Submitted: May 19, 2015
  • Date of Stay: May 2015
  • Source: VRBO, from HomeAway
Ellicott City, MD, Howard

Great experience

  • 5 of 5

The house was great and the owner was one of the kindest people that I have ever met in my life. My overall experience was 100/100.

  • Review Submitted: Feb 25, 2015
  • Date of Stay: Feb 2015
  • Source: VRBO, from HomeAway
South Carolina

Great house for family reunion

  • 5 of 5

We rented Oakland for a family get-together with folks coming from different states. The kid-cousins loved, loved, loved the house, which is rambling and has lots of nooks and crannies for fabulous games of indoor hide and go seek (which didn't bother the grown-ups who had plenty of space away from the kids). We also enjoyed the chickens (nothing like a farm-fresh egg!) and we even caught a few crabs (using the carcass of our Xmas turkey as bait). Even though we had crummy weather in late December, everybody still had a great time.

  • Review Submitted: Jan 2, 2015
  • Date of Stay: Dec 2014
  • Source: VRBO, from HomeAway

Step Back in Time for a Relaxing Vacation

  • 5 of 5

I rented Oakland for a 50th birthday celebration for my best friend. There were 12 of us women and we had plenty of room to sleep and relax and enjoy ourselves without feeling like we were crowded. The house and the grounds are gorgeous. The home definitely is old, but it was very charming. It was the perfect place to spend a fun and relaxing long weekend with good friends. The kitchen is fully stocked - we made dinner one night and had everything we needed to enjoy an Italian feast. We went to dinner at the White Dog Bistro one evening and it was fabulous. The restaurant is only 8 miles from the house. We also spent Saturday in Urbanna Va for the annual Oyster Festival. It was an easy 20-25 minute drive to Urbanna from the home. The property is stunning. We were lucky and had nice weather for November so we were able to enjoy the dock and the gorgeous sunsets. Cathleen was very responsive to my questions. The rental process was so simple and easy. She made sure we had everything we needed for our Girls' Weekend. I would definitely return again - particularly in the summertime when the pool is open and we are able to enjoy the water. I highly recommend the house for family trips.

  • Review Submitted: Nov 10, 2014
  • Date of Stay: Nov 2014
  • Source: HomeAway
Stafford, VA, USA

What a wonderful weekend we had at Oakland!

  • 5 of 5

Great location for us, since we were coming from different parts of Virginia. The house was big enough to fit 11 people very comfortably while still feeling very cozy. Lots of bathrooms. Three of the bedrooms are railroad style, with one accessible only by passing through another. This was no problem for us, but may be an important detail for someone else. Kitchen was well equipped and well-marked. Lots of great historic details and charm in this house! There was lots of porch space and access to the outdoors. We had a great time crabbing off the pier and canoeing. Cathleen was very responsive whenever we had a question. Would recommend Oakland to anyone interested in a restful getaway. Our only problem was getting our dog in the car when it was time to go... He had so much fun; he did not want to leave. He was speaking for the rest of us for sure!

  • Review Submitted: Oct 7, 2014
  • Date of Stay: Oct 2014
  • Source: VRBO, from HomeAway
Northern VA

Fantastic weekend!

  • 5 of 5

Oakland ROCKS! We spent a weekend here for my wife’s birthday and had a truly memorable time. This place is very charming and we felt at home right away. We were quite a large group with kids and a dog but never really ran out of space or things to do on the property. Most of our time was spent outdoors between canoe rides, fishing off the pier, spying on the chickens or simply lounging around, hangin out with good friends and soaking in the spectacular views. The owner – Cathleen - is a true gem! This was our first time renting from VRBO/Homeaway and she has set the bar very high. Cathleen was so incredibly responsive before and during the rental and very kind to accommodate all our requests. It has been a real pleasure working with her. Our next stay at Oakland will be at least a whole week during summer so that we can use the pool and really experience all that this wonderful place has to offer.

  • Review Submitted: Oct 4, 2014
  • Date of Stay: Sep 2014
  • Source: VRBO, from HomeAway


Nearest Airport
40 Miles
Williamsburg Newport News
Nearest Golf
30 Miles
Many options in Williamsburg!
Nearest Train
40 Miles
Nearest Motorway
10 Miles
Route 17, Interstate 64
Nearest Restaurant
5 Miles
Many options in Gloucester and Mathews
Nearest Beach
10 Miles
Mathews has 5 Public Beaches
Car: necessary

Mathews County, the “Pearl of the Chesapeake!” Mathews is Virginia’s second-smallest county land-wise, with over 200 miles of Chesapeake Bay shoreline. Rich in centuries of maritime tradition, the county’s quiet country roads lead past stately historic homes to the river’s edge and a life of boating, kayaking, fishing, sailing, and just plain un-commercialized relaxation. You’ll find a wonderful assortment of specialty shops and restaurants throughout the county, with the majority lining our quaint Main Street in Mathews Court House. Art is abundant and spending the night is simply a great experience. Our annual festivals, such as Mathews Market Days, the Gwynn’s Island Festival, and the Tour de Chesapeake, provide a showcase for community pride and creativity. The Visitor & Information Center is located in the Victorian-era Sibley’s General Store, located at 239 Main Street. Visit Mathews for a weekend, and you’ll be tempted to stay for a lifetime.


Prices & Availability

From $289 Nightly

Prices for this holiday house in Mathews, Chesapeake Bay - Northern Neck

Rental Basis:
per property
Prices quoted in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
Late Spring
18 May 2015 - 7 Jun 2015
2 night minimum stay
for 2 nights
Peak Season 2015
8 Jun 2015 - 7 Sep 2015
7 night minimum stay
for 7 nights
Late Summer/Fall
8 Sep 2015 - 1 Nov 2015
2 night minimum stay
for 2 nights
2 Nov 2015 - 21 Nov 2015
2 night minimum stay
for 2 nights
22 Nov 2015 - 29 Nov 2015
4 night minimum stay
for 4 nights
Xmas Holiday
19 Dec 2015 - 27 Dec 2015
3 night minimum stay
for 3 nights
My Standard Rate
2 night minimum stay
for 2 nights

Additional pricing information

Linen Service $40.00 + Tax
Pet Fee $50.00 + Tax
Tax Rate 5.0%
Notes $500 deposit towards rental required to reserve date; balance of payment is due 60 days prior to visit.

$50 flat pet fee.

Smaller groups/couples may contact me for discounted rates.

June 15 through Labor Day - full week rentals only (Sat 4PM check in -Sat 11AM checkout )

Cancellation Policy

100% refund for cancellations more than 60 days before check-in date.
Enter dates to see total


Accommodation and facilities for this holiday house in Mathews in Chesapeake Bay - Northern Neck

Property Type:
  • house
  • Self-catering
Floor Area:
  • 4800 sq. ft.
Location Type:
  • rural
  • Water View ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking ...
  • Telephone
  • Towels Provided ...
  • Washing Machine ...
  • Wood Stove ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave ...
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Hob ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 4 Bathrooms
  • 1 Separate WC
  • Green bathroom - Toilet , Bath (no shower) , Claw and ball tub, accessed via hallway
    Black and White Bathroom - Toilet , Bath with Shower , Shared between angled ceiling bedroom and waterview bedroom
    1st Floor Half Bath - Toilet
    Master Bath - Toilet , Shower Enclosure , adjacent to master bedroom quaint original pull chain toilet
    Outdoor Shower - Outdoor Shower , Hot and Cold water; adjacent to garage and pool
    Goose bathroom - Shared between Queen bedroom and bedroom with bunks
  • Towels are provided for all baths.
  • 6 Bedrooms, Sleeps 13
  • Ship's Lantern Room - 1 Large Double Bed , Queen bed, dresser, night stand
    Master - 1 Extra Lg. Double Bed , King bed, dresser, non working fireplace, waterview, TV/DVD
    Waterview Room over Breezeway - 2 Single Bed , Two twin beds, DVD/TV with views to river
    Aqua Room - 2 Single Bed , Twin bed with twin trundle; waterview, dresser, DVD
    Blue Room - 2 Bunk Bed , Twin bunk beds, dresser, water views
    Angled Ceiling Room - 1 Single Bed , twin 'boat bed' , built in dresser, TV,waterview
  • 6 bedrooms; 4.5 baths. All bedrooms and all full baths are on the second floor and are accessible via two staircases - one at either end of the house. Towels are provided, however bed linens are to be provided by guests (unless linen service is requested).
  • Books ...
  • DVD Player ...
  • Games ...
  • Satellite / Cable ...
  • Television ...
  • Toys ...
  • Video Games ...
  • Video Library
  • Boat ...
  • Terrace ...
  • Golf ...
  • Kayak / Canoe ...
  • Garden ...
  • Barbecue ...
  • Water Sports Gear ...
  • Events Allowed
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets considered ...
  • wheelchair inaccessible
  • churches
  • cinemas
  • festivals
  • library
  • live theatre
  • marina
  • playground
  • recreation centre
  • restaurants
  • theme parks
  • water parks
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • eco tourism
  • horse riding
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • Shelling
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • hunting small game
  • jet skiing
  • Kayaking
  • mountain biking
  • Parasailing
  • pier fishing
  • sailing
  • bay fishing
  • surf fishing
  • swimming
  • water skiing
  • water tubing
  • wind-surfing
Deep water dock, private location on 3.5 acres, nearby marina (less than 1/2 mile), fire pit, koi pond, canoe and/or sunfish sailboat available upon request.

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