Vacation rentals in Jamestown Island

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Top-rated vacation rentals in Jamestown Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 203 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Dec 2 – 9

G$23,688 GYD per night

Guest favorite

Condo in Williamsburg

4.95 out of 5 average rating, 129 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Oct 13 – 20

G$32,189 GYD per night

Guest favorite

Guest suite in Williamsburg

4.92 out of 5 average rating, 127 reviews

Fun and Open Space Near Everything w/ Hot Tub

Come for the fun to a spacious 1st floor walkout basement just 1 mile from Busch Gardens & Water Country and just 3 miles from Colonial Williamsburg & William and Mary. You'll have a large pool table, bar area, private entrance, hot tub, firepit, coffee bar, and free parking in a quiet neighborhood. The space is part of our home (the bottom floor) w/ private entry. We would love to share anything you want to know about the area, and surrounding cities. Jamestown and Yorktown are also close by.

Jan 11 – 18

G$23,319 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 360 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Nov 8 – 15

G$20,493 GYD per night

Guest favorite

Home in Charles City

4.99 out of 5 average rating, 229 reviews

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Apr 14 – 21

G$56,011 GYD per night

Guest favorite

Guesthouse in Williamsburg

4.98 out of 5 average rating, 302 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

The Freedom Cottage is a charming little cottage comfortable for four can fit six with the sofa bed. You're minutes away from Freedom Park, The Premium Outlets, Jamestown Settlement and 15 minutes from Colonial Williamsburg, Busch Gardens and Water Country. The Williamsburg Winery is also well within reach of our home! Our place offers maximum utility and privacy! We ensure to sanitize every surface, wash every towel and replace every sheet after each guest.

Sep 16 – 23

G$32,059 GYD per night

Guest favorite

Farm stay in Williamsburg

4.96 out of 5 average rating, 315 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Mar 25 – Apr 1

G$40,417 GYD per night

Guest favorite

Home in Williamsburg

4.97 out of 5 average rating, 177 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

Apr 4 – 11

G$26,908 GYD per night

Guest favorite

Farm stay in Toano

4.94 out of 5 average rating, 180 reviews

Farm Stay - Guest Suite w/ Private Entrance

Why not add a little adventure to your trip to the Williamsburg area? Spend your days exploring all the area has to offer and then relax in our cozy retreat. Take a break and stay with us on our homestead. Sit outside on the patio with your cup of coffee (or wine) and enjoy the sights and sounds. We have chickens, geese and some crazy goats that are sure to keep you entertained. All this and less than 15 min to Williamsburg.

Jul 9 – 16

G$18,924 GYD per night

Guest favorite

Guest suite in Richmond

4.97 out of 5 average rating, 587 reviews

Forest Hill Modern Guest House

Located in Richmond's charming and historic Forest Hill neighborhood just blocks from the James River Park and next door to Forest Hill Park. A modern studio space with a queen-size bed and a comfy couch in a private guest house. 1 bath with a spacious shower and simple kitchenette. A great overnight space or comfortable stay for those wanting to explore the cities great food, breweries, parks, and trails!

Oct 10 – 17

G$25,153 GYD per night

Guest favorite

Home in Williamsburg

5.0 out of 5 average rating, 203 reviews

Cozy Single Family Home

Enjoy a little bit of home away from home in our 120 year old fully refurbished house. Property is centrally located with just an 8 minute drive to Historic Colonial Williamsburg, 2 minute drive to Route 199 access, 2 minute drive to the Williamsburg Winery, and 15 minute drive to Busch Gardens. Have morning coffee on the front porch or a BBQ on the back.

Mar 28 – Apr 4

G$35,550 GYD per night

Guest favorite

Guest suite in Williamsburg

4.99 out of 5 average rating, 250 reviews

*Charming 2BR *Patio *Prime Location *Family Fun!

Come relax in our charming guest suite! Perfect for families, we are minutes from the Jamestown Settlement, Colonial Williamsburg, Busch Gardens, and much more. The guest suite is attached to the main house, but has private entry, patio, driveway, and parking. The home sits on 2 acres, and is surrounded by majestic oak trees.

Feb 7 – 14

G$33,364 GYD per night