
Holiday rentals in Dutton
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Top-rated holiday rentals in Dutton
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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!
4.95 out of 5 average rating, 182 reviews
The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.
4.95 out of 5 average rating, 146 reviews
Blue Heron WaterSide
Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?
4.98 out of 5 average rating, 176 reviews
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.
5.0 out of 5 average rating, 322 reviews
The Cottage at Elm Bank
Adorable 2-bdrm, 2-bath cottage on the grounds of Elm Bank, an 8-acre waterfront estate overlooking the Piankatank River and Ferry Creek. Enjoy fishing on the pier, kayaking from the beach, birdwatching from the deck, working out in the gym or playing pickleball on the newly installed court. The property sits on a peninsula known as Piney Point, a welcoming neighborhood with a community dock and boat ramp. Come relax in a park-like setting. You'll find everything you need, nothing you don't.
5.0 out of 5 average rating, 12 reviews
Stunning Beachfront Cottage on the Chesapeake
Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.
4.77 out of 5 average rating, 168 reviews
Cozy Cottage on The North River
Enjoy sunsets and local birds from the waterfront screened in porch in this quiet neighborhood. Bring your boat and enjoy all the water activities- fishing, crabbing, etc. Access to public boat ramp and dock. Cook your fresh catch and enjoy the simpler life. Shed is full of anything you could need for your visit. And you can't forget the outdoor shower! Nightly walks and small town local attractions with good food, shopping and history. Close to Busch Gardens, Williamsburg, and more!
4.96 out of 5 average rating, 96 reviews
Spring is a great time in Gloucester!
Enjoy a peaceful get away at this home in historic Gloucester, Va. This upscale home is located between two creeks that feed into the Piankatank River. It is not waterfront. It is centrally located to Mathews, Gloucester, Urbanna and Gwynns Island. Williamsburg is about a 50 minute drive. This part of Virginia is known for fishing, water sports, beaches and history. Come stay in this newly renovated rancher and enjoy the country on the river. We welcome one small dog under 50 lbs.
4.97 out of 5 average rating, 94 reviews
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.
4.99 out of 5 average rating, 137 reviews
Historic Ware River Cottage at Glebefield
Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.
4.98 out of 5 average rating, 234 reviews
Charming Waterfront Home on Piankatank River!
Amazing waterfront home on the Piankatank River in Gloucester, VA! This one level 1400sf cottage has 3 bedrooms, 2 full baths, a sun room with sweeping views, screened porch, living room with wood burning fireplace & large smart TV, fully stocked kitchen, waterside decks, a terrific fire pit, spacious dock with amazing sunsets AND sunrises, eagles overhead, kayaks and more! Want to bring your boat? There's a community boat ramp 1 minute away.
4.98 out of 5 average rating, 125 reviews
Grey Heron Haven
Relax and unwind in this welcoming and very stylish home. Your worries are sure to be left behind after your stay. This home offers a coastal vibe with a creek view from the front porch. Centrally located 15 minutes to our lovely town and 45 minutes to Williamsburg, VA. We are super host who take great pride in our rentals. We assure you we pay close attention to detail and take meticulous care of our rentals. We hope you come see for yourself.
4.96 out of 5 average rating, 170 reviewsPopular amenities for Dutton holiday rentals
Other great holiday rentals in Dutton

One Level Home | Boats Welcome! | Rockfish | Golf
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The Callie Cottage at Belmont
5.0 out of 5 average rating, 15 reviews
Renhaven Cottage
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Secluded Farmhouse with Access to Private Beach
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Bubba Butler's Cottage
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A "Bitt of Home" in the heart of Gloucester.
4.97 out of 5 average rating, 92 reviewsDestinations to explore
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- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- Fort Monroe National Monument
- USS Wisconsin (BB-64)
- Sandy Bottom Nature Park
- Chrysler Hall





