Vacation rentals in Gloucester County

Guesthouse in Gloucester County

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.

4.98 out of 5 average rating, 165 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!

4.95 out of 5 average rating, 143 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, 229 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.

4.94 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.

4.96 out of 5 average rating, 124 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, 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.

4.94 out of 5 average rating, 526 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, 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.

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, 263 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, 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.

5 out of 5 average rating, 133 reviews

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

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.

Superhost

A wooden dock extends from the water towards the cottage, framed by lush greenery. The main house is visible on the left, with the cottage and a fire pit area situated on the right. A peaceful waterfront setting invites relaxation.

Guesthouse in Gloucester

4.93 out of 5 average rating, 100 reviews

Clay Bank River Front Cottage

Recently updated waterfront cottage 2 bedroom - 2 queen beds, a pull out sofa, 28 private acres on the York River in Gloucester, Va. Great remote getaway with a pool, kayaks and private pier for fishing/crabbing. Lightly traveled river. Access to Yorktown, Newport News, Williamsburg, Jamestown, Richmond, Norfolk, Urbanna. Shares the property with the main house where owner lives.

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Popular amenities for Gloucester County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Gloucester County

A sunlit sunroom features a floral-patterned sofa and a comfortable armchair, providing a cozy seating area. Large windows allow ample natural light, with a wood door serving as the main entrance. A small lamp and a textured area rug add to the inviting atmosphere.

4.91 out of 5 average rating, 55 reviews

Radiant Gloucester House w/ Private Porch!

AliceRating, 5 stars1 month ago

This home has been nicely restored, charming home. Definitely had the “old house feel” in a positive way. Bathroom and kitchen were beautifully done. Air temperature controls in each room, with fans to move air, huge bonus! Bedrooms are quiet, with very comfy beds. Could have slept all day…blinds kept rooms dark if we wanted. Spare bed in front room. Sitting in the back sunroom was so cozy as we sat around chit chatting. Lovely little community with a coffee shop right up the street, walkable distance at that. It seemed very safe, and was a very quiet neighborhood. Within half an hour to Yorktown Beach! If in Gloucester again, I will want to book again. Thank you

Farm stay in Shacklefords

A well-appointed kitchen features decorative floral wallpaper and a large mirror framed in natural wood. A polished countertop is complemented by a wine cooler and glassware on a serving tray. Modern cabinetry is present, along with a window allowing natural light to enter.

4.94 out of 5 average rating, 31 reviews

Blue Heaven in Plainview

MaureenRating, 5 stars1 week ago

Aside from the long drive (45 minutes!) to Williamsburg, Blue Heaven is a perfect family getaway/family reunion spot and very accommodating for a large group (sleeps 10 and is a great entertaining space!). Stacy was extremely responsive and took care of any problems straight away. She also offered local recommendations. While we did not bring our dog, the property does allow them! We thoroughly enjoyed our stay and would highly recommend this property.

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 stars1 month 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.

5 out of 5 average rating, 30 reviews

Home in Middlesex County

Charming Waterfront Cottage Small Beach

EricRating, 5 stars3 weeks ago

We thoroughly enjoyed our stay at the cottage. The location was peaceful and the river view was fantastic. We would definitely stay here again

Superhost

A spacious wrap-around deck is depicted, offering stunning views of the waterfront. Comfortable lounge chairs and a small table are visible, positioned near the home's entrance, with trees framing the scene. The sunset casts a warm glow, enhancing the serene environment.

Home in Hudgins

4.83 out of 5 average rating, 6 reviews

Bayfront Escape | Private Dock, Large Deck & Views

KezeRating, 5 stars1 month ago

Definitely will be going back! Liked it so much I didn’t want to go home lol. Probably rent again in June. Only thing I recommend them to do is to update the pier it is useable. Just use extreme caution! Otherwise absolutely outstanding place!

Superhost

4.64 out of 5 average rating, 33 reviews

Updated Midcentury Waterfront Cottage

CarmenRating, 5 stars2 days ago

As a couple, we were looking for a long weekend getaway on the water but less commercial and this hit the spot! The neighbors to the left were super friendly and told us all about the area, the river and history. If you have T-Mobile you will not have service however once you get on the wifi you will be fine at the house. We were looking to unplug anyways and my boss could not get in touch me so it was a perk! We were there during a heat wave and the house has multiple fans and ac units in every room so staying cool was no worries if you tend to run hot. We caught lots of crabs too! I was warned about nettles however did not see too much of those. Beautiful quiet place to stay. The 1950s appliances were fun to use as well. They really dont make them like they used too!

A laundry area features a washing machine set against a light-colored wall. A countertop hosts neatly arranged toiletries and soft towels. Mirrors above the sink reflect natural light from window blinds. A laundry basket is positioned near the machine, contributing to the functional design.

5 out of 5 average rating, 3 reviews

Country living

MoniqueRating, 5 stars2 months ago

A perfect place to work and relax after a long day at the boat yard.

An open-air seating area with a high wooden ceiling features comfortable furnishings, including a sofa and chairs adorned with colorful cushions. Large windows frame views of the tranquil waterfront and lush greenery, inviting light and fresh air into the space.