Vacation rentals in Gloucester County

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Top-rated vacation rentals in Gloucester County

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Top guest favorite

A modern cottage is presented in a wooded setting, featuring a spacious deck with seating and a spiral staircase. A fire pit surrounded by four chairs is anchored on a green lawn. Soft outdoor lighting adds to the inviting ambiance of the area.

Guesthouse in Gloucester County

4.98 out of 5 average rating, 166 reviews

Modern Cottage w/ Hot Tub, Creekview & Fire Pit

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 street sign stands at the intersection of Main Street and Maple Avenue, featuring a hanging basket of colorful flowers. In the background, a brick building and a parked vehicle are visible, contributing to the town's local character.

Cottage in North

4.95 out of 5 average rating, 143 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!

Top guest favorite

Apartment in North

4.98 out of 5 average rating, 229 reviews

Little Cove Cottage, Couples Retreat/Mathews

Little Cove Cottage: a charming studio in Mathews County with private entrance. Mathews is a rural town with several beautiful beaches close by and many areas to access the water. This apartment offers a small water view of the North River, with a pier and boat ramp just 400 yards away. Bring your Kayaks or use ours. . We are just minutes away from the Mobjack and Chesapeake Bays. Mathews is home to great restaurants with fresh seafood. We also have a wonderful farmer's market. Come enjoy!

Guest favorite

A stacked washer and dryer unit is positioned in a small laundry area. The doorway leads to a brightly lit space featuring a light-colored kitchen. Wooden flooring enhances the overall warmth of the space.

Home in Gloucester

4.94 out of 5 average rating, 187 reviews

Bee Humble Cottage Entire Home

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Humble Cottage" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Top guest favorite

Home in Gloucester Point

4.96 out of 5 average rating, 124 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 historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

Top guest favorite

An open interior space features a loft area with wooden railing above. A cozy sleeping area is visible in the foreground, with a folded white blanket placed on the bed. To the side, a door leads to a private bath, while a kitchenette area includes a mini refrigerator and coffee station.

Guest suite in Gloucester Courthouse

4.98 out of 5 average rating, 122 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.

Top guest favorite

A rustic cabin is surrounded by lush trees, with a welcoming porch showcasing seating. The exterior features wooden panels and large windows, allowing natural light to fill the interior while maintaining privacy. A gravel path leads to the entrance, enhancing the natural landscape.

Guesthouse in Saluda

4.94 out of 5 average rating, 526 reviews

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.

Guest favorite

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 215 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.

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, 101 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 wooden dock leads into a serene waterside area bordered by tall, leafy trees. Two kayaks rest on the grassy shoreline, with the cottage visible in the background, surrounded by greenery. The scene is tranquil, inviting outdoor activities by the water.

Cottage in Gloucester Point

4.94 out of 5 average rating, 264 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

Home in Gloucester

4.98 out of 5 average rating, 170 reviews

The Bee Goode House on Main Street

Welcome to the Bee Goode House! We want our future and returning guests to know of our diligence in sanitizing and cleaning every surface after each guest. Linens are fresh and clean, and there is plenty of private space with a large yard surrounding the house. Relax and enjoy Gloucester Main Street from a 1950's renovated home. From Mid Century Modern furniture and renovated retro appliances, you will be comfortable and hip in our home.

Top guest favorite

An inviting saltwater pool is surrounded by a spacious stone patio, featuring six lounge chairs positioned for relaxation. A dining table for six is situated nearby, all set amidst a serene wooded backdrop with lush green foliage.

Guesthouse in Gloucester

5 out of 5 average rating, 133 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.