Vacation rentals in Gloucester County

Guesthouse in Gloucester County

4.98 out of 5 average rating, 161 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!

4.96 out of 5 average rating, 141 reviews

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

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!

4.98 out of 5 average rating, 224 reviews

Apartment in North

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!

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.

4.95 out of 5 average rating, 183 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.

4.96 out of 5 average rating, 122 reviews

Home in Gloucester Point

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.

Guest suite in Gloucester Courthouse

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.

4.98 out of 5 average rating, 120 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.

4.94 out of 5 average rating, 524 reviews

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

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.

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 213 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.

Cottage in Gloucester Point

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.

4.94 out of 5 average rating, 254 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.

4.98 out of 5 average rating, 168 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.

5 out of 5 average rating, 133 reviews

Guesthouse in Gloucester

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.

4.99 out of 5 average rating, 133 reviews

A woven basket holds a travel guide for Virginia, featuring an image of a wooden structure on the cover, alongside a magazine. A decorative metallic turtle is positioned in the foreground, adding a unique touch to the arrangement.

Home in Gloucester Point

Pointe Haven near Historic Yorktown

Discover the perfect blend of comfort and convenience at Pointe Haven. This newly remodeled 3-bedroom, 1-bath home offers a warm and inviting atmosphere for your stay in the heart of Virginia's Historic Triangle. Just 3 miles from Historic Yorktown and a short drive to the excitement of Busch Gardens and Colonial Williamsburg, Pointe Haven is your ideal retreat to relax and recharge between adventures.

Vacation rentals for every style

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Apartments

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Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Gloucester County vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Gloucester County

Cottage in Gloucester

5 out of 5 average rating, 4 reviews

The Cottage at Elm Bank

NereidaRating, 5 stars1 month ago

Our stay at The Cottage at Elm Bank exceeded our expectations. We traveled to Virginia from New Jersey. A single mom, her two big boys and her little pup. We were in town for a little getaway for Easter weekend. I was looking for some peace and tranquility. When we arrived, we were greeted by Susan and George. They were kind and welcoming. The property is absolutely breathtaking. Our accommodations were cozy and super clean. What stood out the most was all of the personal touches that Susan and George provided. We had a welcome basket waiting for us with many thoughtful things for us to snack on. It was as if they knew exactly what we liked. Susan was very responsive and George was very helpful, he even allowed the boys to use the kayaks and helped them set things up to get into the water. We were able to use the pickleball court and the basketball hoop. They set up wood for a wonderful fire and provided the marshmallows and sticks! It’s a beautiful property with wonderful hosts!

4.97 out of 5 average rating, 35 reviews

Home in Hallieford

Chesapeake Bay Retreat - "Green Bay"

GretchenRating, 5 stars2 months ago

We had a peaceful stay in beautiful surroundings. The home was very clean and provided all the necessities for our stay.

A spacious river house is shown with a blue metal roof and large windows. A paved patio leads to a well-maintained garden featuring colorful flowers, with lush greenery surrounding the property. Outdoor seating is available for relaxation and enjoying the peaceful environment.

4.9 out of 5 average rating, 103 reviews

Waterfront Golden River Watch

micheleRating, 5 stars2 weeks ago

We have been to several AirBnb’s in the Northern Neck area, and they were comfortable. However, the Eventtide home far exceeded our expectations. We are a fishing family and we spent most of our time on the dock fishing. It was fun, peaceful, exciting, private , and carefree. The kitchen windows gave you a beautiful view of the River. OH! I almost forgot to mention that during high tide, the fishing is amazing… spot, croaker, drum, trout… it was an amazing weekend! The owner was extremely nice and communicated effectively in a very reasonable time frame.

4.99 out of 5 average rating, 78 reviews

A modern shower space features natural stone walls in varying tones, creating a textured appearance. A glass block window allows soft light to filter in, while sleek metal handles provide access to the enclosed shower area. The design emphasizes both functionality and style.

Home in Gloucester Point

Amazing Gem! Riverfront, Location, Sunsets, Quite

JesseeRating, 5 stars2 weeks ago

The location was tucked away in a quiet neighborhood overlooking the York River. The house was exceptionally clean and they had everything we needed for our 3 night stay. The Bluetooth speaker was a nice bonus for listening to music while overlooking the river from the sitting room. We had a minor issue with the plumbing, but they quickly reacted and it did not interfere with our trip. We thoroughly enjoyed our stay and would gladly book again in this same location.

4.95 out of 5 average rating, 58 reviews

A screened-in deck overlooks the tranquil waters of the Piankatank River. Furnished with two comfortable chairs and a small glass table, the space is surrounded by wooden railings and views of lush greenery. Natural light filters through, enhancing the inviting setting.

Cottage in Gloucester

Relaxing Riverfront Cottage w/ Boat Dock!

KateRating, 5 stars3 weeks ago

We truly enjoyed our getaway to the river house. The view was worth the rental fees alone. The beds were comfortable, the beds comfortable and the kitchen was swell stocked. We loved the screened in porch and hanging out on the dock. It was a great spot to unwind! Kudos to Kim for helping us find things at the house and making great recommendations.

Superhost

A spacious dining area features a light wood table surrounded by upholstered chairs. Large sliding glass doors allow for panoramic views of the waterfront, with outdoor seating visible on the deck. Soft natural light floods the room, enhancing the serene atmosphere.

Home in Hudgins

4.8 out of 5 average rating, 5 reviews

Chesapeake Bayfront Home with Amazing Views!

WilliamRating, 5 stars3 weeks ago

This waterfront home has gorgeous views. The location is very private and peaceful. Our family really enjoyed fishing from the dock, playing yard games (we brought our own), and just relaxing. Our two-night stay was the perfect amount of time for us to recharge. I would rent the house again.