Jamestown Island Holiday Rentals

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Holiday Rentals in Jamestown Island

Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (300)
"This place was perfect for me, my husband and two adult friends. The views from the kitchen and family room are beautiful and peaceful. The kitchen was well stocked, the gas fireplace worked and the hosts were very good at communicating with us. We had no issues and would highly recommend this home. Thanks Mike and Donna!!"
Cottage on a Private Island in the York River
Beach nearby, beach towels
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
10.0 out of 10, Exceptional, (118)
"We had smooth check-in, property was as described. It's a lower unit, so a bit dark, but perfect for our needs! Clean, well stocked, sofa bed was more comfy than a typical sofabed...communication was great with owners! Great property!"
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!
Fridge, microwave, oven, stovetop
Luxurious 3 Bedroom Condo Sleeps 8!
10.0 out of 10, Exceptional, (75)
"Good home base for our crew to explore the historical area and of course some time at Busch Gardens."
Luxurious 3 Bedroom Condo Sleeps 8!
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Exterior
Steps away from Gloucester Marina & Restaurant
10.0 out of 10, Exceptional, (19)
"Our company was working on a project in the Yorktown area. We needed a comfortable house to accommodate our employees for the duration. This house filled all the needs. The guys loved the house. Wonderful property and great property manager. If you need a place in this area, I highly recommend this property!"
Steps away from Gloucester Marina & Restaurant
Exterior
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
10.0 out of 10, Exceptional, (102)
"This property was one of our better experiences. It was clean, modern amenities, great location and exactly as shown in the pictures. We were centrally located within 20-25 minutes of Colonial Williamsburg, Jamestown and Yorktown. Quiet road less than 5 minutes from shopping. Plenty of dining options within 5 miles."
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6
Indoor pool, outdoor pool
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
10.0 out of 10, Exceptional, (16)
"This property was perfect for our whole family to enjoy Williamsburg/ ( about 10-15 minutes easy drive ) . Plus close to food store etc and a great playground you can drive to. We had both units upstairs and down and the space was great for our group of12 . ( age range 78- 3 months ). The kids enjoyed indoor pool , mini golf and playground. Highly recommend ."
Vacation to remember! Huge family-sized townhouse for 12 near all attractions.
Property grounds
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.8 out of 10, Exceptional, (102)
"While staying in Williamsburg we visited Jamestown & Historical Williamsburg. It was a very easy deive to both places. The host left a binder with local restaurant suggestions. We went to Maurizio's Italian restaurant. It was delicious!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Beach
Busch Gardens-Williamsburg-Fishing-Cornhole-Deck-River View- FIRE TABLE!
9.8 out of 10, Exceptional, (30)
"Get away from the hustle and bustle of Williamsburg and stay here! A very seamless and quick (free) car ferry ride across the James to get to Busch Gardens and Jamestown. This place is great for families. There is even a basketball hoops the kids enjoyed! Lots of space to move and very quiet and serene. We tried 2/3 restaurants in town, both good. Neighbors were friendly and lots of charm. Amanda was fabulous to work with during our stay."
Busch Gardens-Williamsburg-Fishing-Cornhole-Deck-River View- FIRE TABLE!
Fridge, microwave, oven, stovetop
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
9.8 out of 10, Exceptional, (6)
"This is my second time staying here and this place never disappoints. Highly recommend and would stay here again!"
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
On the beach, beach towels
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
9.8 out of 10, Exceptional, (232)
"We truly enjoyed every second that we spent here. Our 9 and 12 year old kids were even sad to leave. They were so skeptical about spending a week without a TV or screetime, but there was never a dull moment. They spent time on the beach, doing the ninja warrior course, playing games outdoors, and my son even kayaked for a bit despite it being quite chilly during our stay. One night we used the firepit and had hot dogs and s'mores. Indoors, there were endless options of books and games. There is...
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
Interior
Relaxing 1 bedroom 2019 Camper beside the Seven River
9.8 out of 10, Exceptional, (10)
"Although the actual camper was not the one advertised, our stay was filled with all the expected amenities Kimberly described. In a previous review someone mentions the rooster, he was quite pleasant, not at all like described in their review. The camper behind ours was closer than I would expect and not in the description, but it was not a total bother, I just adjusted the shades appropriately for privacy. Kimberly & her family were AMAZINGLY FRIENDLY! My 4yo was invited to meet the children,...
The price is AU$230
per night
7 May - 8 May
Relaxing 1 bedroom 2019 Camper beside the Seven River
Property grounds
Private 5-acre Waterfront Peninsula with Beach
9.6 out of 10, Exceptional, (25)
"We had a great time staying here and will certainly look to stay again in the future! 5 stars!"
Private 5-acre Waterfront Peninsula with Beach
Private kitchen
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
9.6 out of 10, Exceptional, (4)
"Bungalow was exactly as advertised. Liked the self check in and out. 1 bed, 1 trundle, 1 bathroom. We liked that we could bring our 4-legged family members. The kitchen lacks some essential needs (like a toaster) but we ate out most meals anyway and could heat leftovers in the microwave. No place to hang a jacket for those cool outings, but we made do laying it in the unused office space. Supplied dog bowls were a treat. A hook for the leash would be a recommended addition since counter space is...
Cozy Marina Home, Pet Friendly, Free Parking, huge yard for pets and boats
Beach
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, (106)
"We all - seniors to toddlers - enjoyed our stay here! Wonderful to be on the river, and also convenient to Williamsburg!"
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Property grounds
Chickahominy River Home Close to Williamsburg
9.4 out of 10, Exceptional, (10)
"Lovely location to relax and spend time with family. The woods and water are beautiful and an easy 25 minute drive to Williamsburg. House was very clean and our teenagers loved their separate space downstairs. Owner was great to work with an responded quickly to our questions."
Chickahominy River Home Close to Williamsburg
Outdoor dining
Uncle Bill's Lodge & Soccer Pool Showdown
9.4 out of 10, Exceptional, (6)
"Perfectly clean and comfortable but no privacy. Pet friendly but neighbor allowed their dog to come to fenced yard at all hours which made my 1 dog bark. Not sure if neighbor was owner. Great fenced yard but as I stated, no privacy. Homes close by even in backyard. Fine for families who want to visit from out of town visiting Busch Gardens/Water Country and CW as backyard is entertaining and home is affordable. Just not what we were looking for. Photos and description made us feel it would be...
Uncle Bill's Lodge & Soccer Pool Showdown
Property grounds
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
9.4 out of 10, Exceptional, (23)
"The condo was well kept and clean. The furniture was comfortable and in great shape. The condo was close to Busch Gardens and Williamsburg. I would definitely recommend it to friends and family. "
Book A Piece of History at Kingsmill Resort in Williamsburg Virginia!
Exterior
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (44)
"Our grandchildren came for several visits and overnights. It was great. The cottage is very user friendly and was quiet. The surrounding areas uncluding paddock was a bonus for our Shetland sheepdogs. The walking trails were fine. We had a fantastic stay."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Beach
Golf Course Studio - Kingsmill, Minutes to Busch Gardens & Colonial Williamsburg
9.2 out of 10, Wonderful, (46)
"For the price this is a very nice deal for a get away. The bed was comfy and the location was ideal for our purpose. Would recommend for a great deal. We will be back. Thank you."
Golf Course Studio - Kingsmill, Minutes to Busch Gardens & Colonial Williamsburg
Interior
Delightful 1 Bedroom RV Near Ft. Eustis
9.0 out of 10, Wonderful, (2)
"We hadn’t stayed in an RV before, so this was a unique experience for us. Very clean & cozy accommodations and located close to many tourist attractions in the surrounding area. Easy parking out front was helpful, and the detailed & friendly communication with the host was also appreciated."
The price is AU$168
per night
7 May - 8 May
Delightful 1 Bedroom RV Near Ft. Eustis
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Jamestown Island you may be interested in

Garden
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
3.0 star property
8.8 out of 10, Excellent, (1012)
"Very convenient for Colonial Williamsburg. Rooms a bit dated. Lots of kids. Breakfast fair and very non eco friendly."
The price is AU$211
per night
14 May - 15 May
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Indoor pool, outdoor pool, pool umbrellas, pool loungers
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2356)
"This hotel/resort is amazing! Beautiful grounds to walk through, pretty lakes, lots of geese and turtles to watch. If it weren’t so hot this week we would have taken more advantage of all the activities. Having a full kitchen and two bathrooms was fantastic!"
The price is AU$131
per night
20 May - 21 May
Hilton Vacation Club The Historic Powhatan Williamsburg
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers
Vacation Village At Williamsburg
3.0 star property
8.6 out of 10, Excellent, (1007)
"I really enjoyed my mini vacation everything was wonderful I just wish the hot water for the hot tub in our room stay hot long enough to fill the tub lol but other than that my family had a great time we really enjoyed the indoor pool amd got to use the outdoor pool our first day arriving we definitely planned to revisit again!"
The price is AU$370
per night
8 May - 9 May
Vacation Village At Williamsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Jamestown Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamestown Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamestown Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jamestown Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamestown Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamestown Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamestown Island holiday rentals we have selected for you start as low as AU$168 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jamestown Island rentals

At Expedia, we put the best Jamestown Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamestown Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamestown Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamestown Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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