Holiday rentals with breakfast in Gloucester County

4.99 out of 5 average rating, 73 reviews

Aldrich House B&B Lewis Room

A spacious & unpretentious atmosphere serving a full hot breakfast & located just outside the historic area. Tom,a licensed tour guide of CW,Jamestown & Yorktown, loves history & manages the B&B while Sue works at The Cheese Shop. Enjoy our hospitality & home as a myriad of guests have done with delight through our 20yrs of sharing our home. CW(2 blocks),William & Mary(1.25 miles),Restaurants(.25 mile),Busch Gardens(3 miles), shopping & golfing nearby.B&B is available for weekly rental(call us).

4.94 out of 5 average rating, 82 reviews

Aldrich House B&B Anderson Room

4.94 out of 5 average rating, 34 reviews

Aldrich House B&B Patton Room

A great, spacious place to stay with uncluttered rooms. We offer an unpretentious atmosphere serving a full hot breakfast & located just outside the east end of the historic area. Tom, a licensed tour guide of CW, Jamestown & Yorktown, loves history & manages the B&B while Sue works at The Cheese Shop. Enjoy our hospitality & home as a myriad of guests have done with delight through our 20yrs of sharing our home. CW(2 blocks), W&M College(1.25 miles) B&B is available for weekly rental(call us)

4.5 out of 5 average rating, 4 reviews

Virginia Retreat | Gym. Pool. Free Breakfast.

At Best Western Williamsburg Historic District, colonial charm meets modern comfort. The hotel immerses you in a history-loaded location while offering modern amenities like an indoor pool, fitness center, and on-site dining. Perfect for history buffs and families alike, the property is close to Busch Gardens and Water Country USA. It’s the ideal spot for exploring Virginia’s rich past while enjoying creature comforts. ✔ Pool ✔ Free breakfast ✔ Fitness room ✔ Free parking ✔ Nearby golf

Private room in Yorktown

5 out of 5 average rating, 9 reviews

Marl Inn Bed and Breakast - Butterfly Room

Our cozy bed and breakfast is located in the historic village of Yorktown. The inn is only two blocks from Yorktown Beach. This room has a small refrigerator and a Keurig machine. A full breakfast ($17 plus tax/person) or a continental breakfast ($10 plus tax/person) is available onsite for an extra fee. Please message us when you book to let us know if you will be adding breakfast. Museums, restaurants and retail shops are all within walking distance from the inn. CGTC is 2 miles away.

Historic Haven! 3 Spacious Units, Pool, Parking

Positioned right next to a beautiful golf course and in the heart of the city center. Enjoy the convenience of being just a short walk away from excellent shopping opportunities in the vibrant Merchants Square. For thrill-seekers, Water Country USA and Busch Gardens Williamsburg are accessible and offer a day of excitement for all ages. Don't miss the chance to visit the renowned Colonial Williamsburg Visitor Center, highly recommended for immersing yourself in the rich history of the area.

5 out of 5 average rating, 123 reviews

Home in Deltaville

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Guest house in Cobbs Creek

5 out of 5 average rating, 16 reviews

Piankatank Riverfront Perch in Mathews County, VA

Make peaceful & playful memories on the Piankatank River in Mathews County VA. Cozy Condo-style riverfront space with enclosed breezeway, fenced yard, paved access to sandy beach waterfront & covered dock where you can catch crabs and fish, or catch some sun kisses. Fully equipped for your River Escape with family and/or friends. Sleeps up to 6 with queen bed, twin trundle & bunk beds. Access to 2+ acre property and waterfront “crabshack”. Explore & Enjoy at your own pace.

Guest suite in Gloucester Courthouse

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.

Townhouse in Williamsburg

4.33 out of 5 average rating, 15 reviews

Beautiful 1 bedroom accommodations Kings Creek

King’s Creek Plantation is set apart from other resorts, offering large, luxury, vacation homes. They feature decor and details expected in deluxe accommodations with decks for optimal outdoor enjoyment. Large jetted tubs adorn the master bedroom suite. There are fireplaces, beautiful tile and plush carpet, laundry washers and dryers, and kitchens featuring granite counter tops and top grade appliances. For vacations with only the finest, enjoy Kings Creek!

Private room in Gloucester

5 out of 5 average rating, 35 reviews

Serenity’s Porch Queen, Historic Gloucester VA

Stay in an upscale place that’s near everything you want to visit. The Porch Queen features a first-floor queen bed with sliding to walk out onto the beautifully landscaped patio and gardens. You will have access to a shared first-floor half bath and a full bath and common areas on the second floor, including a den and kitchenette with complimentary daily snacks, coffee, and tea. Enjoy pasture and garden views from every window in the house.

4.98 out of 5 average rating, 168 reviews

Home in Gloucester

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for rentals with breakfast in Gloucester County

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with breakfast

Private room in Newport News

4.96 out of 5 average rating, 131 reviews

Private Bedroom & Bath Suite for Females Only

MelissaRating, 5 stars7 months ago

This is a great host family who went above and beyond to make my stay comfortable, enjoyable and safe. They went from being hosts to friends during my stay.

Private room in Newport News

KarlRating, 5 stars44 months ago

Lee Hall

Renee was a very kind, helpful, and accommodating host, for our family of six. The location is super convenient to Busch Gardens. This was my first time staying at a property which was not one where you get the "entire home". My expectations were met in terms of that, and her descriptions of the property and the experience were accurate. I wish her the best of luck in her future endeavors on Airbnb.

Private room in Kilmarnock

MargueriteRating, 5 stars110 months ago

Private Suite ~ sleeps up to 4 guests

Lovely setting and very comfortable accommodations. Am hoping to go back again soon.

5 out of 5 average rating, 5 reviews

Home in Lancaster

The Perfect View Virginia Tiny Home

JenRating, 5 stars4 weeks ago

This adorable tiny home is just a perfect getaway, but with a super comfortable bed, and very peaceful surroundings. Brenda couldn't have been nicer! We thoroughly enjoyed our very low-key time and will definitely return.

Home in Cape Charles

Sweet Bay | Chesapeake Properties

EricRating, 5 stars5 months ago

Fantastic property in the private Bay Creek community that I have to come to love as one my favorite vacation destinations. A treasure of a home that made my annual New Year's vacation getaway another memorable one.

Home in Cape Charles

ThomasRating, 5 stars9 months ago

Pebble Beach East | Chesapeake Properties

Chesapeake Properties was such a wonderful host/manager. Quick responses, great recommendations, and extremely helpful. The house was spotless and comfortable. It was steps to the life center and few more to the beach. Just such an enjoyable stay. Thank you for all you did!!

Private room in Newport News

4.67 out of 5 average rating, 72 reviews

Comfortable place to stay in a quiet neighborhood

JasonRating, 5 stars23 months ago

I take this like home, the floors needs sweeping i sweep trash needs taking out I takes. Wherever you sleep to me it's home.

Private room in West Point

4.76 out of 5 average rating, 160 reviews

Near Ground Zero of US History

Belle ERating, 5 stars2 weeks ago

Bret is a marvelous host with an excellent library in the guest room! The bed was extremely comfortable and it was nice to have a porch to sit on and gaze at the garden. Bret brought us coffee and a light breakfast each morning. He’s a lovely person and very gracious.

Show all

Bed and breakfast rentals with breakfast

4.96 out of 5 average rating, 52 reviews

Williamsburg Sampler - Lord Nelson Chamber

LauraRating, 5 stars2 weeks ago

My fiancé and I had a wonderful stay at this charming bed and breakfast in Colonial Williamsburg. From start to finish, the experience was top-notch. The host was incredibly communicative and made sure everything was smooth and stress-free. The room was beautifully decorated, spotlessly clean, and had all the amenities I needed for a comfortable stay. The rest of the house was just as lovely—warm, welcoming, and tastefully furnished, with a cozy outdoor space perfect for relaxing. The innkeeper was so kind and hospitable, and the breakfasts each morning were absolutely delicious—clearly made with care and attention to detail. I highly recommend staying here if you’re visiting the area. It’s a perfect blend of comfort, charm, and hospitality.

Bed and breakfast in Williamsburg

4.71 out of 5 average rating, 7 reviews

Private 2BR Cottage with Breakfast - Cedars B&B

MihaiRating, 5 stars21 months ago

We've had a great time. The place has a wonderful location and we've had a great time in our (brief) stay. We hope to get there for a longer visit someday soon.

4.93 out of 5 average rating, 72 reviews

Williamsburg Manor - Russel House Green Room

RikkiRating, 5 stars1 month ago

Exterior is more beautiful in person! Very convenient location to colonial Williamsburg and shopping. If you are looking for a historical experience feel, this is the place you should stay.

5 out of 5 average rating, 3 reviews

Washington Suite - A Williamsburg White House

SaraRating, 5 stars23 months ago

Wonderful stay!! My flight was canceled and I needed a place to stay last minute! They were flexible. I got in right away. They had wine and treats ready for guests. It truly was a gem of a stay. I’m so glad my flight got canceled. Best hospitality!! And met incredible people at breakfast. Which btw was also amazing!! Quiche with baked oatmeal and a side of ice cream.

DanielleRating, 5 stars3 months ago

The Rhododendren-King-Luxury-Ensuite with Shower-G

Absolutely loved our stay! Karen was amazing and so helpful. Our room was one of the cleanest airbnbs I e been in yet! The most comfortable bed and pillows. We slept amazing and felt right at home. The breakfast was so delicious and she was able to accommodate my gf requirements. We will definitely be coming back!

5 out of 5 average rating, 3 reviews

Sunny Queen Room with Breakfast - Cedars B&B

MichelineRating, 5 stars3 months ago

Alex and staff are great hosts, we frequently stay here we love it that much! I’ve taken my boys and their friend or have just stayed with my finance. Already browsing my next stay 💕💕

Private room in Kilmarnock

4.75 out of 5 average rating, 28 reviews

Elegance Room - Back INN Time

LeighRating, 5 stars3 weeks ago

My mom and I had a lovely night away at Lisette’s place. The room was perfect for 2 people for the night and was very comfortable. We really enjoyed the delicious breakfast made by Lisette before we checked out. The grounds were very peaceful, and I was able to enjoy a little time on the front porch to have a glass of wine and read (while mom napped). The Inn is convenient to everything we wanted to do and not far from the shops and restaurants In Kilmarnock. I’m already planning a return trip!