Holiday houses in Gloucester Point

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!

4.99 out of 5 average rating, 183 reviews

Home in Gloucester Point

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

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.

Cottage in Gloucester Point

4.99 out of 5 average rating, 140 reviews

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

Cottage in Gloucester Point

4.94 out of 5 average rating, 255 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.

4.96 out of 5 average rating, 264 reviews

Home in Yorktown

Modern-farmhouse Retreat

Beautifully updated home nestled among the trees just along the edges of Colonial National Historic Park. Great location to everything you might want to see! A few minutes bike ride to the gorgeous Colonial Parkway; go shopping at the Outlets; explore historic Williamsburg, Jamestown and Yorktown; spend the day at the beach, or just rest in this quiet haven! High Speed Internet and cozy atmosphere... put your feet up and relax!

4.99 out of 5 average rating, 134 reviews

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.

Superhost

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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Gloucester Point holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Gloucester Point

4.98 out of 5 average rating, 64 reviews

Loft in Poquoson

Bull Island Getaway!

AaronRating, 5 stars5 days ago

My wife and I were in Poquoson for our step daughters HS graduation. I had been stationed at Langley from 2006-2010 so it was like a trip down memory lane. Gabby’s accommodations were perfect as it was about 2 miles from our step daughter’s home. It does not have a full kitchen, but get out and explore the area to eat!!!! 10/10!!!!

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.

4.99 out of 5 average rating, 76 reviews

Welcome to this Waterfront Home with Amazing Views

KyleighRating, 5 stars1 month ago

Our crew stayed here for work and had no complaints! They loved the area and loved the hosts!! They all said it was supper clean and would stay again!!

Superhost

Holiday home in Gloucester County

4.8 out of 5 average rating, 44 reviews

Waterfront 4 bedroom home with marina facilities

ShawnRating, 5 stars2 weeks ago

We had a great vacation! It was a beautiful location that was peaceful and restful. The house was exactly like the pictures and description. We liked having all the games for our family time.

4.93 out of 5 average rating, 14 reviews

Home in Port Haywood

Relax & Heal Cottage Near Ocean & Forest Retreat

CalebRating, 5 stars4 days ago

I think this is the best Airbnb we have ever stayed at. the house was spotless, it had an amazing shower, and had everything we needed. Elenny was so accommodating with our dog as well, and was flexible with check in and check out. this was a great experience and we would recommend this spot and host to anyone looking for a relaxing place to stay!

4.95 out of 5 average rating, 42 reviews

Guesthouse in Poquoson

The Retreat at Lamb's Point

KendallRating, 5 stars4 days ago

Beautiful and serene location on the water! Watching the sunset every night from the chairs outside was so peaceful. The space is comfy n cozy (especially the couch) and has everything you might need! We stayed there a week while handling some personal family affairs and Pam was so accommodating. It was so relaxing to have her space to come back to: we made meals, used the grill, fire pit, and played games! 10/10 recommend. :)

5 out of 5 average rating, 48 reviews

Apartment in Yorktown

Granny-Chic Suite: King Bed & Washer/Dryer

EllenRating, 5 stars2 weeks ago

Beautiful, clean, peaceful - everything I needed for my stay in the area. Great hosts, excellent bed, pillows and linens. The plush bathrobe was a nice touch! I felt like a queen in a castle. Would definitely come back!