Holiday houses in Gwynn Island

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

This beachfront cottage is the perfect get away from a busy & hectic life to slow down & enjoy each others company! Situated just over 70 miles from Richmond, this home shares waterfront views of the Chesapeake Bay. Fishing, swimming, kayaking & sun await you at the Sand Crab! What makes it so great? Just steps outside and you're on the beach Newly renovated Cable, high speed Wifi, Netflix 2 screen porches Kayaks and paddle boards Just over 10 minutes to grocery store, ABC, and other shops

Location · Family · Beach

Unique & bright two-bedroom waterfront cottage

Relax and leave your worries behind at this tranquil cottage in the quiet town of Deltaville, Virginia where the Rappahannock River meets the Chesapeake Bay. Deltaville is known for marinas, sailing, boating and fishing. We are located at the end of a peaceful private road. You will have your own private dock for wading, swimming, fishing and other water activities. Whether you are hanging out by the firepit or swinging in the hammock, I am sure you will have a wonderful time at Tranquil Seas.

Location · Family · Amenities

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

Location · Family · Checkout

Waterfront Guesthouse II on the Rappahannock

The “Beach 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 beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Value · Family · Getting around

Mathews Gwynn's Island Chesapeake Bay- Sand Beach!

Gwynn's Island waterfront & beachfront cottage looking at the Chesapeake Bay! You will enjoy the wrap around deck eating dinner, the views & breezes. The home offers on first floor - kitchen, living, dining area, full bathroom and master bedroom and screened porch. Second floor offers 2 bedrooms and full bathroom. The home offers in the kitchen utensils, dishes for 6, cook ware, and small appliances. Public boat landing on Milford Haven as you enter Island. Bring your own linens & towels.

Location · Value · Condition

Sunset Haven

Enjoy the Island life in this newly renovated, cheerful 3 bedrooms, 2 bathroom cottage with 3 porches with water & sunset views. This charming 1900’s farmhouse is situated on historic Gwynns Island in Mathews County, a waterman’s delight. Small town with locally owned shoppes and restaurants is less than 10 minutes away. Public boat landing is less than 2 miles away on the island at the Hole In The Wall Restaurant. Bring your paddle boards, kayaks, & boat! This is a non-smoking property.

Location · Family · Layout

Gwynns Island Waterfront Getaway

A lovely waterfront cottage with stunning bay views and the best sunsets on the East Coast. Sliding glass doors create the feeling of being right on the water, even when indoors. You can crab, fish, kayak, grill, and swim directly from the backyard. It's incredibly peaceful and relaxing. Just a mile away is a newly renovated island restaurant with a bar and a wide variety of food options. The house was passed down from my father, and all proceeds from Airbnb go towards making improvements.

Location · Family · Beach

Irvington Cottage - Vineyard Birdhouse

Beautiful & peaceful 3 bedroom (1 King, 1 Queen, Twin Beds), 3 bath cottage with screened porch nestled in the woods in a quiet neighborhood with nature trails and dock. Perfect getaway for adults/family. Walk or bike to the charming town of Irvington. Explore the shops and restaurants in the area. Enjoy sunset dinner at nearby river restaurants; eat oysters! Close to Tides Inn. Premium Cable TV, high -speed WIFI for your convenience. Note: NO PETS, no smoking, no parties allowed.

Value · Family · Accuracy

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Value · Family · Bathroom

Garden Cottage in Downtown Mathews

Wake up surrounded by greenery, sip coffee on a quiet porch, and unwind in the hot tub after a day exploring coastal Virginia. Sugartoad Cottage is a calm, plant-filled retreat designed for couples who want comfort, privacy, and walkable access to the best of small-town Chesapeake Bay life. Though located on Mathews Main Street, the cottage feels surprisingly secluded, with gardens, multiple decks, and thoughtfully designed outdoor spaces that make it easy to slow down.

Location · Value · Hot tub

The Sandbar on Gwynn’s Island

Escape to The Sandbar on Gwynn’s Island- a relaxed Chesapeake Bay retreat with a rare private sandy beach, endless water views, and unforgettable sunsets. Designed for easy coastal living, this waterfront getaway features incredible indoor-outdoor spaces, kayaks, a paddleboard, and plenty of room for families and friends to spread out and unwind. This is the place you will want to return to year after year.

Family · Quiet · Comfort

Waterfront w/Floating Dock, Kayaks~Family Home

Cove Place is a newly renovated, 1 -story home with a dock and boat/trailer parking on 4 secluded acres. There is a smart tv in every room including the screened porch. Close to Zoll Vineyards (4.1 miles away), a chef owned winery that focuses on food and beverage pairings in their tasting room and Under the Stars Farm (8.6 miles), a family owned and operated lavender farm.

Family · Value · Layout