Guest house holiday rentals in Gloucester County

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.

Modern Cabin with Hot Tub, Fire Pit, Amazing 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!

Piankatank Riverfront Perch A, Mathews VA

Perched on the Piankatank River with sandy beach and large covered dock ~ you can relax, fish, crab and enjoy the peaceful setting. This cozy, well-appointed space is part of a duplex-style property guesthouse with potentially shared breezeway, property & dock. The fully fenced yard adds privacy and security, making it great for families & pets Inside, you'll find two bedrooms (queen & full), full kitchen, washer/dryer, living room with waterviews & cozy dining. Adventure/Relaxation awaits!

Charming guest house on Jackson Creek

Treat yourself to this unique cozy cottage with views of the creek complete w/ kayaks and bikes. All you need for a weekend get away with equipped kitchen, bath w/ shower and outdoor shower. Relax, enjoy the peace and quiet by the Piankitank at the Chesapeake Bay. This listing is for the guest cottage behind Paddler's End, the main home on the property. The cottage is available when the main house is not booked. If you are interested in renting the cottage please inquire about availability.

BlueBird Nest

Keep it simple at this peaceful and centrally-located oasis, tucked away in coastal Virginia. Our newly renovated 1BR/1BA barn apartment on 3 acres is ideal for those who want to live like a local. We are 3 miles from the heart of the American Revolution in Yorktown, and Yorktown Beach, and a short drive to area attractions in the Historic Triangle. Unwind after a day of exploring with a glass of wine on the balcony or enjoy the firepit and the view. This is an upstairs apartment with stairs.

Little England Farms’ Hunt House on Sarahs Creek

Historic property hosting a one bedroom and loft cottage. This home sits directly on the bank and beach of Sarahs Creek. Newly renovated and stocked with all the essentials. The Hunt House is a part of Little England Farm circa 1716. 20 minutes to Gloucester Courthouse 25 minutes to Busch Gardens 30 minutes to Colonial Williamsburg The Farm is a beautiful place to relax , take walks, sit on the beach, enjoy all the history in the surrounding area. Boat slip available for extra fee.

Waterfront-ChesapeakeBay Dream Believer Mathews VA

WATERFRONT is place to stay, perfect for family trips, single solitude or just a couples get-a-way! Close to shops, grocery and restaurants. Comb the beaches on the Chesapeake Bay, go fishing, kayaking, catch crabs right off the pier. Gazebo for sunset gazing. Grill on your patio & enjoy the water views . Visit the Donk’s Theatre Music Show. Attend Mathew’s Market Days ! Free concerts many times a year at Williams Wharf. Mathews is a wonderful town to visit … the “Pearl of the Chesapeake “ .

Cedar Pointe Carriage House on Jackson's Creek

Modern, 2-story carriage house with dock and view of charming Jackson's Creek. Perfect for relaxing getaway, housing out of town guests, fun fishing weekends, fishing off dock, and home base for visits to Williamsburg, Jamestown, and Yorktown. Dock your boat steps away from carriage house depending upon size of vessel. Pool table, game table, cable TV with HBO & Showtime, collection of DVDs with DVD player, and gas grill. Can walk to community pool, tennis courts, and playground.

Cozy 2B 1BA Private Suite

Private 2 bed 1 bath. Fully furnished with queen bed in master and twin trundle in spare. Living room, dining room, kitchen with Keurig and coffee pot, dishwasher, gas oven, microwave, and refrigerator. Enjoy your own private screened in porch. Gas fireplace. Smart TV in living room and in master bedroom. All utilities and Wi-Fi included. No smoking and no pets. Close to Busch Gardens, Water Country, Colonial Williamsburg, Yorktown Beach, Wineries, Breweries, Parks, and more!

Airy Loft Guest House near Gloucester Village

Bright and airy second story apartment five minutes from the restaurants and shops of Gloucester Courthouse. Beautiful marsh and wooded views across the creek from a bald eagle nesting site. Picture touring the iconic sites of Virginia's Historic Triangle (30 to 45 minutes away) or visiting the delightful town of Mathews (25 minutes), then retreating to your comfortable loft in a waterside forest. Please note there's no direct water access and you will have to climb stairs.

Piankatank Riverfront Perch B, Mathews VA

Make peaceful & playful memories on the Piankatank River in Mathews County VA. Cozy Condo-style riverfront space with enclosed breezeway, fenced yard, paved access to sandy beach waterfront & covered dock where you can catch crabs and fish, or catch some sun kisses. Fully equipped for your River Escape with family and/or friends. Sleeps up to 6 with queen bed, twin trundle & bunk beds. Access to 2+ acre property and waterfront “crabshack”. Explore & Enjoy at your own pace.

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.