Vacation rentals in Port Haywood

Magnolia Cove waterfront 1BR upper cottage

Welcome to Magnolia Cove cottage! Travel back in time along a magnolia-lined lane for a charming waterfront stay. On 11+ private acres, the guest upper cottage is separate from owner's 1937 manor home. Water surrounds the property on 3 sides. Enjoy kayaking in the Put-in-Creek and swim/fish right off your private dock. 6+ft deep water docking available for boat owners. Bike/drive minutes into the peaceful town of Mathews VA w/ galleries, shops and restaurants. Local beaches min away.

Stylish Creekside Cabin w/ HotTub, Parklike views.

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

Waterfront Escape • Dock, Views, Peace & Kayaks

Relax and unwind with the whole family at this Rappahannock River paradise in Lancaster Virginia. This spacious, restored historic home is the perfect getaway for your family vacation, girls' trip, or retreat. Enjoy picturesque views from the screened in porch overlooking the river or cozy up around the firepit. Comfortable modern décor, water views from most rooms, and private dock. Please read Property Description for house information, area shops, restaurants, and things to do.

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.

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.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Piper’s Landing: Relaxing beach house near the Bay

This home is ideal for those who enjoy nature, as it is close to Bethel Beach Park and Nature Preserve and has easy kayak access via a public dock within 2000 feet. The home has two double beds, one king bed, and several couches up stairs . Our perfect getaway includes two kayaks, and a couple adult bicycles, You are only 2 Minutes from Bethel Beach Nature Preserve 15 minutes from Mathews 60 Minutes to Virginia Beach 60 Minutes to Williamsburg/Jamestown

The Tulgey Wood

Lose your worries in The Tulgey Wood. Just like Alice down the rabbit hole, you will be transported to a quiet and peaceful land, back to nature, with all of the comforts of home. Surrounded by acreage on a private road, explore the woods, watch the deer, or take the kayaks out on the river. All this tranquility is 5 minutes from a cozy downtown area, complete with grocery store, gas station, and a variety of restaurants to satisfy any taste.

Serenity

Enjoy the natural serenity of this spacious waterfront hideaway on the historic Antipoison Creek (so named by Capt John Smith), minutes to the Chesapeake Bay by boat or car. The area offers boating, fishing, a nature trail and an abundance of wildlife (deer, turkeys, waterfowl, bald eagles, osprey. otters and more) on this 7 acre property. Water views, king bed, sofa and full kitchen with dinette.

"The Little Red Cabin" aka The Galley

Called the "The Galley". This is the first cabin built on the property. Right on the water with views of the Bay and beach. Galley kitchen, bedroom, small bathroom with shower, family room with a fireplace and dining area. Big screened in porch w/ fabulous breezes. Literally, right on the water!!! NO PETS. Parking for 1 car.