Guesthouse holiday rentals in Gloucester County

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.

Secluded River Hideaway

Peaceful setting on the Rappahannock River. Amazing views that will take your breath away. Entire guest house that 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 Rivah!

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!

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.

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.

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.

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, 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.

Creekside Guesthouse - Dock and Pool on 10 acres

With stunning views overlooking Bland Creek, this guesthouse is the perfect place to unwind or start your adventure. This two-bedroom apartment is nestled high in the treetops, perfectly situated on 10 acres of wooded and coastal beauty. When the time comes to explore, guests are only minutes away from eclectic shopping and dining in historic downtown Gloucester, with Williamsburg and Richmond an easy 45 minutes away.