Vacation rentals in Gloucester

Guesthouse in Gloucester County

4.98 out of 5 average rating, 162 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, 142 reviews

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, 225 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!

4.95 out of 5 average rating, 184 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

4.98 out of 5 average rating, 121 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

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

4.94 out of 5 average rating, 256 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, 169 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.

Loft in Gloucester Courthouse

4.98 out of 5 average rating, 325 reviews

Marshfield Guesthouse on river near Williamsburg

Marshfield Guesthouse is the perfect place for a getaway on the river, a home base for those exploring the historic Colonial Triangle and a unique experience for those looking for an alternative to hotel lodging. Come enjoy the beautiful sunsets on the river! The guesthouse is located a short drive (30 miles) from Williamsburg, Yorktown and Jamestown!

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Popular amenities for Gloucester vacation rentals

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BBQ grill

Laptop-friendly workspace

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Other great vacation rentals in Gloucester

4.9 out of 5 average rating, 92 reviews

Severnly Pointe Cottage Waterfront Retreat

HayleyRating, 5 stars1 month ago

This is the second time I've stayed at Tamara's place and I would absolutely stay again. The place is exactly what you expect and they have excellent instructions. Wonderful people, peaceful location, and you always know what to expect.

Superhost

Home in North

4.77 out of 5 average rating, 22 reviews

Lazy Day Getaway in Mathews

JasmineRating, 5 stars2 weeks ago

My family and I enjoyed this place very much and plan to come back for our anniversary . It was very peaceful although some of the neighbors were doing some type of drill work late at night and startled our sleeping 2 year old . Other than that I felt at home #countrygirl

Guesthouse in Gloucester Point

4.92 out of 5 average rating, 92 reviews

BlueBird Nest

SavannahRating, 5 stars1 week ago

Dawn and Rich knew that we were going to be spending our wedding night at their place and left us a sweet little card to congratulate us on this special event. My new husband and I appreciated this sentiment. The place was very clean and welcoming. I would highly recommend!

4.95 out of 5 average rating, 19 reviews

Cabin in Gloucester

Bill's Island

GeorgiaRating, 5 stars3 weeks ago

'A diamond in the ruff'. Our first AirBnB and we absolutely loved the cabin. Had everything we needed & very clean. We had wonderful weather, nice breeze off the water. Fish were biting. Very quiet . A great getaway cabin. Our hostess Lorena was great, checked on us to see if we needed anything. Well stocked kitchen. Thank You Lorena!

Superhost

Villa in Williamsburg

4.89 out of 5 average rating, 19 reviews

Quiet Villa with Access to Amazing Amenities

LauraRating, 5 stars1 month ago

It was a quiet and lovely space with a ton of amenities (pool, mini golf) and close to downtown Williamsburg and local and state parks. The kitchen was great! Some of the other appliances inside were less quiet (vacuum, washing machine, dryer), but it was nice to have the appliances!

4.89 out of 5 average rating, 94 reviews

Farm stay in Gloucester

Historic Farmhouse. Peace & Quiet on 5 acres

RodneyRating, 5 stars1 week ago

Dream weaver farmhouse was great! Loved the tree swings, fire pit, and the nice relaxing nature.

4.97 out of 5 average rating, 95 reviews

Charming Waterfront Home on Piankatank River!

AnnRating, 5 stars1 month ago

This adorable home was just what we were looking for....a place to get away from the noise and business of life. The views of the water from the house and the pier were the highlight. The whole family sat out on the pier/deck overlooking the beautiful, quiet river taking turns on the kayaks and stand up board. We watched birds, gazed at the ever changing skies, and talked and laughed. Later in the evening, we sat by the fire pit and roasted marshmallows. The house is really cute with the kitchen in the center. It had all of the pots, pans, gadgets, etc we needed to prepare our meals. I loved how there were several rooms (sunroom, living room, and screened porch) for us to hang out which provided a space for all of our needs. Many thanks to Elizabeth for sharing this lovely home with us.