Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-829-7076
Book Online or call HomeAway Booking Assistance 888-829-7076

Waterview Villa on Chesapeake

Bedrooms 4
Property type house
Minimum Stay 2 nights


About the property

Great water view get-away for family and friends

The majestic property of Villa Wenona sits on a beautiful lawn and wooded ¾ acre lot, yards from the Chesapeake Bay at the southern tip of Deal Island, MD. Enjoy exquisite sunsets from the comfortable sun room or the stunning balcony located off one of two master bedroom suites!

Our home was built to provide comfort and privacy. On the second floor you will find two master bedroom suites! One with s beautiful balcony, gorgeous views, a queen size bed, sitting area and a private full bathroom with double sinks. Across a wide hallway you will find a second master bedroom suite , with queen size bed, sitting area and full private bathroom. Enjoy the bay views from the two bedrooms downstairs, one with a full size bed, the other a twin trundle. These comfortable bedrooms share a 3rd full bathroom with large stand up shower. Relax in the roomy living room, watch TV, play games, or simply curl up on the sofa with a good book in front of the large, stone fireplace.

Karen and Jeff Cross
Member since: 2016
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
March 22, 2018

About Karen and Jeff Cross

Jeff and I (Karen) are the new owners of Villa Wenona. We are so excited. We have both enjoyed Maryland's Eastern shore for years. Jeff is a collector of wooden duck decoys and I grew up on the water. Jeff likes to fish, hunt, bird watching and of course decoy collecting. I like swimming, and biking, and nature adventures!

The picture above is my family reunion at Villa Wenona. We had a fantastic time with family coming from GA, CT, FL, NJ, PA and MD. What a great time!

Karen and Jeff Cross purchased this house in 2016

Why Karen and Jeff Cross chose Deal Island

Jeff and I fell in love with Villa Wenona the first time we saw it. The fantastic views, water access and low key life style. Lots of sunny days and wildlife. Great neighbors and friends.

Did you know that word, Wenona, comes from the Sioux Indians and means "a fun loving, spiritual, big hearted, sexy, ambitious, optimistic woman. Someone you can rely on when times are good and bad. What's not to love!!!

What makes this house unique

Villa Wenona is the perfect place to kick back and enjoy with friends and family. Lots of space in the house and outside. Activities for everyone! And the view, well I just can't say enough about the sunsets, boat watching and incredible views of the Bay. You will love it too!

Guestbook comments from the owner

Thank you Karen!

Our family really enjoyed the lovely comforts of Villa Wenona - the house and yard were enjoyed by all! Vinnie and I enjoyed talking to Wanda too. We love crabs and ate them daily that we purchased from the crabbers. A real pleasure! Maybe we'll be in touch down the road.

Lee Ann
Aug 2016
  • 1 of 2


Deal Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: Flexible / Check-out: Flexible
  • Max. occupancy: 10
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • Events Allowed
  • children welcome
  • non smoking only
Location Type:
  • Beach View ...
  • Rural ...
  • Water View ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 3 Bathrooms
  • Bathroom 1 - toilet , shower , Jack and Jill between bedrooms 1 and 2
    Bathroom 2 - toilet , combination tub/shower , First Master bedroom
    Bathroom 3 - toilet , combination tub/shower , Located in suite with 2nd Master bedroom
  • 4 Bedrooms, Sleeps 10
  • Bedroom 1 - 1 double , Bedroom with Jack and Jill bathroom with bedroom2
    Bedroom 2 - 2 twin/ single , Shares Jack and Jill bathroom with bedroom 1
    Bedroom 4 - 1 double , 2nd Master bedroom with private bath
    Bedroom 3 - 1 king , 1 sleep sofa /futon , Master bedroom 1 with private bath. Balcony waterview
  • Additional pull out couch in living room and futon in Master bedroom 1. All bedrooms have individually controlled air conditioning remotes.
  • Books ...
  • DVD Player
  • Games ...
  • Satellite / Cable
  • Stereo ...
  • Television ...
  • Toys ...
  • Video Library ...
  • Balcony ...
  • Bicycles
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • 4 bicycles
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
  • autumn foliage
  • bay/sound
  • churches
  • marina
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • hiking
  • hunting
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • water skiing
Deal Island is a quiet community with great neighbors, harbor, biking, birding, nature preserves, kayaking, swimming, fishing charters, and pier fishing. Jeff and I love the area. Feel free to contact us with any questions you may have. We want you to have a fantastic vacation!


Wonderful! 4.8/5 -
(14 traveler reviews)

78% Complete
21% Complete
0% Complete
0% Complete
0% Complete
Waterview Villa on Chesapeake
average rating of 4.785714 based on 16 reviews
Forked River, NJ

Villa on Chesapeake

  • 5 of 5

Beautiful views of the sunset. House is clean & tidy. Beds comfortable. Plenty of room for a large family. Karen and Jeff were great to work with and answered questions quickly. Would highly recommend!

  • Submitted: Nov 9, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Great Place

  • 5 of 5

We had a wonderful time! Beautiful place to stay. We enjoyed our time spent out on the water fishing, and crabbing. Thanks again for the use of your house....

The Weilers

  • Submitted: Oct 23, 2017
  • Stayed: October 2017
  • Source: HomeAway
Owner's Response: Thank you! We are so glad you had a good time! The Cross'
Did you find this review helpful?
0 0


  • 5 of 5

We loved staying here. The house has the perfect layout for gathering with friends--the kitchen and living room open design facilitated conversation, cooking, relaxing. The dining area and sunroom allowed for side conversations, reading, relaxing. The waterview was an added bonus! The rooms and bathrooms are all gorgeous, spacious and well-kept. The owners have thought of everything. We will definitely return!!!

  • Submitted: Oct 16, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Beautiful! Great for large groups! Kitchen is fantastic!!

  • 5 of 5

This is an awesome home on Deal Island. Deal Island is a sleepy little, non commercial town. Our stay was in off season, and didn't see anyone else while there until Friday afternoon. The house is lovely. Plenty of room for large crowd.

  • Submitted: Oct 1, 2017
  • Stayed: September 2017
  • Source: HomeAway
Owner's Response: Thank you for your kind words. We are glad you enjoyed staying at the Villa Wenona!
Did you find this review helpful?
0 0

Beautiful property!

  • 4 of 5

Great home. Plenty of room. All you need is there. We stay here every year and hope to continue our tradition.

Tom Midkiff

  • Submitted: Sep 7, 2017
  • Stayed: August 2017
  • Source: HomeAway
Did you find this review helpful?
0 0

Great times at Villa Wenona!

  • 5 of 5

This was the second time we vacationed at Villa Wenona on Deal Island and we loved it both times. We have a large family and there is plenty of space for all of us. The kitchen is great! The dining room table fit all of us comfortably. We saw an eagle fly into the trees on the property, hang out and eat a fish, several hummingbirds and beautiful sunsets all without even leaving the house. There is a beach about five minutes from the house that is beautiful. The locals are friendly and helpful. We loved it and hope to go back.

  • Submitted: Aug 14, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0


Car: recommended

Deal Island is a wonderful place to kick back and enjoy life. There are kayaks and bikes at the house. Two great beaches are close by and fishing charters are right down the road at the Wenona Harbor. Ocean City is about 1.5 hours away and Salisbury is about 30 minutes away with grocery stores and shopping, Ward Museum, and a free zoo!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Pet Fee $50
Damage Deposit $300

Pets - Well-behaved dogs (max 2), with our approval and a $50.00 fee PER dog.
Extra person fee - $50 per person beyond 10, 12 max. This fee is PER RENTAL, not per night and is not calculated using BOOK it NOW button.

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.