Guesthouse vacation 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!

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.

Peaceful Retreat w/ Fire Pit & Spa Services

Country living at its best! Quiet...peaceful & very special place to relax, release, and rejuvenate. We are surrounded by beautiful wineries, which are all minutes away. Gorgeous views of nature and seasonal flowers. Separate from the main house, our guest suite offers awesome privacy & comfort. You will enjoy this very quiet, cozy, peaceful retreat. It is the perfect hideaway with the utmost charm. Board Certified Reflexologist on the premises is available for appointments. So AMAZING!

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.

Secluded River Hideaway

Peaceful setting on the Rappahannock River. Amazing views that will take your breath away. Guest cottage overlooks Mechams Cove and the Rappahannock River. Amenities include water access with kayaks and SUP included. Full kitchen and two full bathrooms with all you need for a wonderful getaway. Situated between Urbanna, Deltaville, and Irvington, the house is centrally located for you to explore the entire Northern Neck. Amazing restaurants and activities abound. Welcome to the River!

Serene Country Cottage

Nestled in the forest, on 35 acres is an ideal getaway for any small family. The kitchen is well-equipped and there are excellent dining options nearby. Beaches are close by with rental options and quaint shops in the picturesque nearby town. The 900 sq ft cottage has 2 bedrooms upstairs with a full bath and a tub. Downstairs is a family room, full kitchen, ½ bath, dining area, front screened porch and back deck overlooking the woods. The main house is owner occupied.

Modern Lofty Tranquil 757

Take it easy at this unique and tranquil getaway. Private loft with private entrance and separte parking. Close to all military bases, beaches, theme parks an historic Williamsburg/Jamestown/Yorktown. Get energized by early mornings echoed by birds singing and peaceful nights under the stars while feeling the breeze from the nearby river. Dip into the pool to cool of during hot summer days. New Loft apartment with modern comforts . Please check pool availabilty with host.

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

The Freedom Cottage is a charming little cottage comfortable for four can fit 5 with the sofa bed. You're minutes away from Freedom Park, The Premium Outlets, Jamestown Settlement and 15 minutes from Colonial Williamsburg, Busch Gardens and Water Country. The Williamsburg Winery is also well within reach of our home! Our place offers maximum utility and privacy! We ensure to sanitize every surface, wash every towel and replace every sheet after each guest.

York River Penthouse

Relax at our guesthouse, aka the "Penthouse" on the York River! This cozy space features: 2 queen bedrooms, loft w/ 2 twin beds (great for kids), one full bath, well stocked kitchen and a laundry nook with an LG ThinQ washer/dryer combo. There's more outside! You have your own PRIVATE dock (sink w/fresh water), beach area, 2 kayaks, fire pit, Charcoal BBQ, games and large grassy backyard. Perfect for riverfront fun, sunsets and making memories.

The Retreat at Lamb's Point

Make some memories at this unique and family-friendly place. Located on the Poquoson river with a view of the Chesapeake Bay, it is conveniently located with easy access to area tourist attractions, beaches and military bases. Please take the time to read the information below and familiarize yourself with this listing. It is designed for family and friends. Commercial bookings are prohibited without prior arrangement and approval.