Holiday rentals in Gwynn

1860s Cottage Getaway! Fenced Yard-Dog Freindly!

Gwynnsville Cottage: Historic Charm, Private Pool! A Boaters Dream! A charming and unique 1860 farmhouse renovated for modern comfort. This private retreat offers a blend of historic character and contemporary convenience. We've lovingly updated this 165-year-old cottage to ensure your family feels comfortable and relaxed. It retains its unique quirks and charm, you'll find the modern amenities you need for an unforgettable vacation. (Please note the low ceiling on the stairs – mind your head!)

The Nook; Peaceful 2 bedroom cottage by the bay

Relax or go-for-it! The Nook is a stylish cozy cottage with great indoor/outdoor space. With water view and access including pier and boat ramp enjoy your coffee on the deck before taking to the water in one of the two kayaks or canoe or enjoying a bike ride (4 available) to get up close with nature. Catch fish, crabs or just a sunburn while enjoying time on the water. When ready there's plenty of shopping, eating and beaching to do in nearby towns! All topped off with a sunset over the water!

Waterfront Guesthouse I on the Rappahannock

The “Bay House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has a beautiful Bay view and includes access to our private beach & dock (w/ guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath w/ jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and 1/2 bath.

Salty Sisters on the Bay. Enclosed yard on the Bay

The studio apartment(above main house) is a short walk to the beach (which is on the property.) Studio is fully furnished including linens, towels, hairdryer, pots, pans, etc. Coffee shops and restaurants within a mile, marinas are less than a mile to launch your boat. Fabulous views of the Bay, full kitchen, spacious bath and your own private back yard. There is a dock to fish from or sit and watch the sunrise and set. There is also a small beach. Dog friendly , sorry no cats.

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and the best sunset on the east coast. Sliding glass doors make it feel like you are on the water even when you’re inside. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

The Oyster House

If a quiet country setting is your relaxation, this is your place. Surrounded by open fields that attract deer, turkey, osprey, ground hogs, this is natures haven. Outdoor seating around a permanent firepit or covered backporch with bar top overlooking wildlife. Renovated 2019. Yet, just seconds from downtown Deltaville. House accommodates wheelchairs. Bonus Event Room (The Spat) for 4 people available for extra cost. Ask re: price/availability.

Mystic Seahorse Cottage & game room

Welcome to our quiet corner of Gwynn’s Island! Walk to the beach, relax in the backyard, ride a bike, kayak, or book a fishing excursion; there's so much to do here. The cottage is clean and stocked with everything you need for a relaxing visit. Drive 10 minutes to Mathews for great restaurants and shopping, or an hour to Yorktown, Jamestown and Williamsburg. Come relax and enjoy some Island Time with us!

~ Beautiful Gwynn’s Island Waterfront Home ~

Welcome to our historic waterfront home on Gwynn's Island, VA. This family-owned property offers a relaxing stay with unbeatable sunsets, abundant wildlife, and a private dock with deep water access. Available for weekly rentals June - August, plus long weekends in the off-season. Message us about rates for longer stays.

Little Gray Beach House

Gwynn's Island cottage with magnificent views of the Chesapeake Bay! Located between 2 white sandy beaches--perfect for swimming or fishing. Great spot for kayaking and/or biking around historic island. Spectacular sunrises! Great bayside deck for cookouts, bird watching, and frequent dolphin-spotting!