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Holiday houses in Gloucester Courthouse

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Top-rated holiday rentals in Gloucester Courthouse

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Top Guest favourite
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, 218 reviews

Modern Moody Creekside Cottage w/ HotTub & FirePit

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!

Top Guest favourite
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
4.94 out of 5 average rating, 144 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.

Guest favourite
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
4.94 out of 5 average rating, 166 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 favourite
The exterior of a blue, two-story cottage is showcased among lush green trees. Spacious decks are visible on both levels, and a gravel driveway leads up to the entrance. The surrounding yard features manicured grass and a border of decorative stones.
Apartment in North
4.98 out of 5 average rating, 250 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!

Top Guest favourite
A spacious living area features a large sectional sofa and an armchair with an ottoman. Natural light enters through multiple windows, illuminating the wood flooring. A smart TV is positioned near a console. A dining area with seating is visible in the background.
Home in Gloucester
4.98 out of 5 average rating, 101 reviews

Welcome to this Waterfront Home with Amazing Views

Welcome to our waterfront Air Bnb. Nestled along the Ware River, this unique property offers an unforgettable experience that combines comfort, luxury, and the most amazing sunsets. The open kitchen, living, and dining areas offer amazing views of the river. The interior is tastefully decorated with the perfect blend of modern elegance and coastal charm. Come and experience coastal living where the water becomes your playground and every moment is a celebration of nature's splendor.

Top Guest favourite
The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.
Tiny home in Diggs
4.95 out of 5 average rating, 216 reviews

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Top Guest favourite
The exterior of the cottage features a landscaped yard with a green lawn and flower beds. The front porch is highlighted by potted plants and a flag, framed by windows with awnings that provide shade. Tall trees surround the property, creating a serene environment.
Home in Gloucester
4.95 out of 5 average rating, 222 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 favourite
Guesthouse in Gloucester
5 out of 5 average rating, 174 reviews

Summer Escape - Dock, Pool, Firepits, & Kayaks

A waterfront summer retreat tucked into 10 secluded wooded acres above Bland Creek, perfect for long days and relaxed evenings - Screened porch with water views and cool creek breezes - A Pool is available for rent for private use (open Memorial Day–Labor Day) - Dock, kayaks, fishing, firepits, and direct water access -Outdooring dining options and family-friendly - Immaculately clean and thoughtfully stocked for a seamless stay - Just minutes from downtown Gloucester

Top Guest favourite
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, 130 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 favourite
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, 229 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 favourite
A single-story brick house is surrounded by well-maintained landscaping, featuring a covered patio area with colorful seating. Vibrant flowering plants and a tidy lawn enhance the outdoor space, while a tree-lined background adds greenery to the setting.
Home in Gloucester
4.97 out of 5 average rating, 191 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.

Guest favourite
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, 571 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.

Popular amenities for Gloucester Courthouse holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Gloucester Courthouse

Guest favourite
A scenic view of the waterfront showcases the Piankatank River and the Chesapeake Bay, framed by tall trees. The lush green lawn leads towards the water's edge, with light clouds appearing in the bright blue sky.
Home in Hallieford
4.94 out of 5 average rating, 48 reviews

Chesapeake Bay Retreat - "Green Bay"

Top Guest favourite
The exterior of the retreat is framed by lush greenery and tall trees, showcasing a brick structure with large windows. A well-maintained lawn leads to the water's edge, where a rock boundary is visible. Outdoor seating is provided on the patio, enhancing the tranquil setting.
Apartment in Cobbs Creek
5 out of 5 average rating, 44 reviews

Cozy Waterfront Apartment with Pickleball Court

Top Guest favourite
Cabin in Gloucester
4.97 out of 5 average rating, 31 reviews

Bill's Island

Top Guest favourite
The coastal cottage exterior features a modern blue facade with white accents. Stairs lead to a welcoming entrance, complemented by a small porch with seating. A water view is visible in the distance, with kayaks stored nearby on the grass.
Home in North
5 out of 5 average rating, 33 reviews

Salt & Pine in Mathews, VA

Guest favourite
Tiny home in Port Haywood
4.93 out of 5 average rating, 15 reviews

The Tulgey Wood

Top Guest favourite
A spacious bed is positioned against a softly lit wall, complemented by decorative pillows. A bedside table features a lamp, providing warm lighting, while a second lamp stands on the opposite side, enhancing the cozy ambiance. Natural light enters through a window with blinds.
Apartment in Gloucester
4.95 out of 5 average rating, 62 reviews

Eclectic and Cozy Apartment

Guest favourite
A charming cottage is depicted, framed by lush green grass and mature trees. The front features a covered porch with multiple large windows, allowing for ample natural light. A serene atmosphere is created by the surrounding open space, inviting relaxation and connection to nature.
Home in Port Haywood
4.96 out of 5 average rating, 46 reviews

Relax & Heal Cottage Near Ocean & Forest Retreat

Top Guest favourite
Two elegant glasses of red wine are positioned on a wooden railing, overlooking a calm body of water. The sky is painted with soft hues of pink and orange as the sun sets, reflecting the tranquil atmosphere of the waterfront.
Home in Locust Hill
4.98 out of 5 average rating, 45 reviews

Bubba Butler's Cottage

Frequently Asked Questions

  • What are the best places to stay in Gloucester?

    Stays in Gloucester center, waterfront neighborhoods, and rural areas let guests explore local shops, outdoor spaces, and cultural sites. Choose accommodations that match your style, from family-friendly homes to cozy retreats.

  • What are the best things to do in Gloucester with kids?

    Explore nature parks, interactive museums, and community playgrounds around Gloucester. The area has hands-on activities, trails, and seasonal family events that encourage kids to discover local ecology and history.

  • What are some of the best things to do in Gloucester?

    Explore historic sites, art galleries, nature trails, and waterfront parks in and around Gloucester. The area has seasonal festivals, local shopping, and opportunities for outdoor adventure like kayaking and hiking.

  • How is the weather in Gloucester?

    Gloucester has cooler winters with temperatures from 32–49°F (0–10°C), and warm, humid summers near 71–87°F (22–31°C). Spring and fall bring mild afternoons and variable rainfall, so layers are often useful.

  • When is the best time to visit Gloucester?

    Late spring and early fall are frequently suggested for milder temperatures, fewer rainy days, and seasonal festivals. Summer brings warm afternoons around 83°F (28°C), while winters are cooler and often quieter for visitors.

  • What are the best places to visit in Gloucester?

    Historic downtown, waterfront parks, and local museums are often recommended places to explore in Gloucester. Art galleries, farmers markets, and scenic trails invite visitors to discover the area's culture and nature.

  • What are some hiking trails in Gloucester?

    Explore riverside nature paths, woodland trails, and park loops around Gloucester. These areas invite visitors to encounter regional wildlife and enjoy peaceful landscapes during their hike.

  • What are some family activities we can do in Gloucester?

    Families can engage in hiking, picnics in community parks, nature center visits, and craft workshops at local museums. Seasonal outdoor festivals and public art events offer interactive experiences for all ages.

  • What are some of the best day trip ideas from Gloucester?

    Consider visiting historic towns, wildlife preserves, and waterfront communities just outside Gloucester. Art galleries, local food markets, and scenic walking areas nearby create engaging day trip experiences.

  • Are there any pet friendly accommodations available in Gloucester?

    Many accommodations in Gloucester welcome pets, especially in central neighborhoods and near outdoor parks. Check specific stay listings for pet policies and amenities such as fenced yards or walking trails.

  • What are some local tips for visiting Gloucester?

    Locals recommend exploring both main streets and hidden trails, trying seasonal produce from farm stands, and joining public events or markets to connect with community traditions. Dress for changing weather and bring an appetite for local food.

  • What is Gloucester known for?

    Gloucester is known for its colonial history, vibrant arts scene, and scenic outdoor spaces near the Chesapeake Bay. The community highlights traditions through local festivals, heritage sites, and seasonal food culture.

  • What are the best hidden gems to explore in Gloucester?

    Look for tucked-away art studios, farm stands with local produce, and smaller nature preserves around Gloucester. Community markets and historic walking paths provide quieter, locally rooted discoveries.

  • What are the best foods to try in Gloucester?

    Gloucester has locally rooted flavors like fresh seafood, Virginia ham, and classic southern-style dishes. Seasonal produce, crab cakes, and regional desserts are frequently suggested by residents and visitors.

  • What should I bring for a trip to Gloucester?

    Pack layers for variable temperatures, rain gear for occasional showers, and comfortable shoes for outdoor activities. Sunscreen, insect repellent, and reusable water bottles are often recommended for nature outings.

  • What is the nightlife in Gloucester like?

    Gloucester's nightlife centers around casual cafes, pubs, and live music venues. Community spaces occasionally host open mic nights, art shows, and cultural events, creating a relaxed evening atmosphere.

  • What are the most popular events or festivals in Gloucester?

    Gloucester hosts community festivals featuring local art, seasonal foods, and historic reenactments, especially around late spring and fall weekends. Annual fairs and cultural celebrations draw residents and visitors.

  • Are there family friendly vacation rentals in Gloucester?

    Gloucester has family friendly vacation rentals with spacious layouts, access to outdoor spaces, and amenities designed for all ages. Neighborhoods close to parks and community centers are often preferred by traveling families.

Destinations to explore