Jamestown vacation rentals

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Top-rated vacation rentals in Jamestown

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

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Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 200 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.

Mar 17 – 24

G$23,726 GYD per night

Guest favorite

Guest suite in Williamsburg

4.93 out of 5 average rating, 125 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.

Sep 1 – 8

G$23,357 GYD per night

Guest favorite

Cottage in Gloucester

4.97 out of 5 average rating, 194 reviews

"Bee Haven" Cottage Retreat

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" 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.

Sep 17 – 24

G$24,906 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 359 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.

Oct 31 – Nov 7

G$20,634 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.

Feb 11 – 18

G$56,100 GYD per night

Guest favorite

Guesthouse in Williamsburg

4.98 out of 5 average rating, 300 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.

Aug 22 – 29

G$33,644 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.

Jan 14 – 21

G$40,481 GYD per night

Guest favorite

Home in Williamsburg

4.97 out of 5 average rating, 176 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.

Feb 26 – Mar 5

G$26,951 GYD per night

Guest favorite

Farm stay in Toano

4.94 out of 5 average rating, 178 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 7 – 14

G$18,954 GYD per night

Guest favorite

Guesthouse in Gloucester

5.0 out of 5 average rating, 103 reviews

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.

Dec 27 – Jan 3

G$34,483 GYD per night

Guest favorite

Cottage in Williamsburg

4.89 out of 5 average rating, 370 reviews

Colonial Cottage II old Williamsburg charm

Parties are not allowed. This is a charming historic cottage that backs up to the Colonial Pkwy. Across the road is an equestrian farm that offers a magnificent sunset view from the brick patio. The back of the property is surrounded by a fairytale wooded landscape. Minutes from Jamestown Island.. Colonial Williamsburg and much more including Busch Gardens and water country. Convenient location near William and Mary

Jun 2 – 9

G$30,640 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.

Jan 26 – Feb 2

G$35,606 GYD per night