Vacation rentals with outdoor seating in Gloucester County

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Top-rated outdoor seating rentals in Gloucester County

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Top guest favorite

A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.

Guesthouse in Gloucester County

4.98 out of 5 average rating, 181 reviews

Moody Cabin w/Hot Tub/Fire Pit & Amazing view.

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!

Guest favorite

A warm living area is captured, featuring a comfortable leather couch and a cozy yellow chair. A bottle of wine and two glasses are placed on the counter next to a sign inviting guests, while soft lighting creates a welcoming ambiance.

Guesthouse in Gloucester Point

4.93 out of 5 average rating, 111 reviews

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.

Top guest favorite

A two-story blue home is surrounded by trees, featuring a spacious deck with railings accessible from the upper level. A gravel patio area with chairs and a fire pit is visible on the ground level, complemented by neatly maintained greenery.

Home in Gloucester Point

4.96 out of 5 average rating, 134 reviews

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

Guest favorite

A cozy living space features a large white sofa and wicker chairs, set on a patterned rug. A wooden coffee table is centered in the room, while a dining table with rattan chairs is seen in the background. Natural light filters through white window blinds.

Cottage in North

4.95 out of 5 average rating, 152 reviews

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!

Guest favorite

A serene waterfront view features two kayaks resting on the grass under tall trees. A wooden dock extends into the water, surrounded by lush greenery and a clear blue sky. The area offers a peaceful setting for outdoor activities.

Farm stay in Cardinal

4.91 out of 5 average rating, 190 reviews

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

Top guest favorite

A vibrant sunset paints the sky in shades of orange and pink, casting reflections on the water. Silhouettes of a dock and surrounding trees create a serene waterfront scene, highlighting the natural beauty of the location.

Home in North

5 out of 5 average rating, 100 reviews

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.

Top guest favorite

A spacious grassy area is surrounded by mature trees, providing shade. The landscape features a clear blue sky and a backdrop of rolling greenery, creating a serene outdoor environment perfect for relaxation or exploration.

Guest suite in Gloucester Courthouse

4.98 out of 5 average rating, 126 reviews

Elm Grove Farm Guest Cottage

Our guest cottage is the perfect retreat for a quiet getaway or a quick commute to local historical sites. We are located on a family farm property dating back to the 1880's. Although the old farmhouse is gone our home with attached cottage is filled with decor built by the owner with reclaimed wood from the original home. We are adjacent to Beaverdam Park and located 2 miles from Main Street which boasts the historic Gloucester Courthouse dating back to 1651.

Guest favorite

A historic sign for Glebefield, established in 1795, is positioned among mature trees. Bright yellow flowers add a pop of color in the foreground, contrasting with the earthy tones of the surrounding greenery, creating a serene and inviting atmosphere.

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 219 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.

Top guest favorite

A serene waterscape is presented, highlighting the cottage set among lush trees. A dock extends into the water, flanked by boats, with soft ripples reflecting the clear blue sky. The tranquil environment suggests a peaceful retreat by the water's edge.

Cottage in Gloucester Point

4.99 out of 5 average rating, 148 reviews

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

Top guest favorite

The living room features a cozy arrangement of sectional sofas and a swivel chair, surrounded by light-toned hardwood flooring. A stone fireplace serves as a focal point, complemented by shelves adorned with decor. Sunlight filters through the windows, enhancing the bright and airy ambiance.

Home in Gloucester

4.96 out of 5 average rating, 114 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.

Guest favorite

A serene view of a wooden dock extending into the calm waters of Sarah's Creek, surrounded by trees. Two kayaks, one green and one blue, are positioned on the grassy shore, with a charming cottage visible in the background.

Cottage in Gloucester Point

4.95 out of 5 average rating, 277 reviews

The Cottage on Sarah's Creek

Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

Top guest favorite

A serene outdoor seating area is nestled among colorful autumn leaves, with four adirondack chairs arranged around a wooden platform. The setting sun casts a warm glow over the peaceful view of Bland Creek and the marsh, enhancing the natural beauty of the landscape.

Guesthouse in Gloucester

5 out of 5 average rating, 142 reviews

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.