Vacation rentals near Jamestown Settlement
We found 1,667 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Jamestown Settlement, take a look at vacation rentals to find the perfect home base for your trip. Whether you're staying in a vacation rental with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Jamestown Settlement
Showing deals for:Nov 14 - Nov 21
Image gallery for Lovely 2 BR Condo in 4💎 Historic Golf Resort
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Lovely 2 BR Condo in 4💎 Historic Golf Resort
Williamsburg, VA
10% off
Price is CA $370
CA $370
CA $3,359 total
CA $3,359 total
includes taxes & fees
Image gallery for Historic Yorktown Waterfront Home
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Historic Yorktown Waterfront Home
Yorktown, VA
10% off
Price is CA $356
CA $356
CA $3,299 total
CA $3,299 total
includes taxes & fees
Image gallery for ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
9.89.8 out of 10 rating
Exceptional
(241 reviews)
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest
Spring Grove, VA
15% off
Price is CA $518
CA $518
CA $4,424 total
CA $4,424 total
includes taxes & fees
Image gallery for The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
1010 out of 10 rating
Exceptional
(62 reviews)
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Williamsburg, VA
10% off
Price is CA $446
CA $446
CA $4,021 total
CA $4,021 total
includes taxes & fees
Image gallery for Squeaky Shores Gloucester, VA Waterfront York River Oasis
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Squeaky Shores Gloucester, VA Waterfront York River Oasis
Gloucester, VA
5% off
Price is CA $678
CA $678
CA $6,234 total
CA $6,234 total
includes taxes & fees
Image gallery for Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.49.4 out of 10 rating
Exceptional
(124 reviews)
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Hayes, VA
10% off
Price is CA $403
CA $403
CA $3,424 total
CA $3,424 total
includes taxes & fees
Image gallery for The Inn at Woodmont Plantation, Gauthier Vineyard's Winery & Event Center
9.89.8 out of 10 rating
Exceptional
(26 reviews)
The Inn at Woodmont Plantation, Gauthier Vineyard's Winery & Event Center
Barhamsville, VA
10% off
Price is CA $929
CA $929
CA $7,692 total
CA $7,692 total
includes taxes & fees
Image gallery for James River Waterfront with spectacular views across the river from Williamsburg
1010 out of 10 rating
Exceptional
(137 reviews)
James River Waterfront with spectacular views across the river from Williamsburg
Surry, VA
10% off
Price is CA $432
CA $432
CA $3,692 total
CA $3,692 total
includes taxes & fees
Image gallery for Private Beach & Pier - James River Beach Cottage - Jamestown & Williamsburg
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Private Beach & Pier - James River Beach Cottage - Jamestown & Williamsburg
Surry, VA
23% off
Price is CA $318
CA $318
CA $2,837 total
CA $2,837 total
includes taxes & fees
Image gallery for Farm-stay, Diversified Working Farm, Agrarian Setting
1010 out of 10 rating
Exceptional
(18 reviews)
Farm-stay, Diversified Working Farm, Agrarian Setting
Wakefield, VA
15% off
Price is CA $293
CA $293
CA $2,540 total
CA $2,540 total
includes taxes & fees
Image gallery for Relax And Reconnect With Expansive Views Of The Historic James River
1010 out of 10 rating
Exceptional
(51 reviews)
Relax And Reconnect With Expansive Views Of The Historic James River
Claremont, VA
25% off
Price is CA $336
CA $336
CA $2,938 total
CA $2,938 total
includes taxes & fees
Image gallery for Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area
Surry, VA
17% off
Price is CA $303
CA $303
CA $2,721 total
CA $2,721 total
includes taxes & fees
Image gallery for Secluded Riverfront Home + Deep Water Boat Dock - Between Williamsburg-Richmond
1010 out of 10 rating
Exceptional
(10 reviews)
Secluded Riverfront Home + Deep Water Boat Dock - Between Williamsburg-Richmond
Charles City, VA
20% off
Price is CA $448
CA $448
CA $4,733 total
CA $4,733 total
includes taxes & fees
Image gallery for Riverfront Cottage w/ Private Beach Near Wmsburg
1010 out of 10 rating
Exceptional
(20 reviews)
Riverfront Cottage w/ Private Beach Near Wmsburg
Surry, VA
10% off
Price is CA $367
CA $367
CA $3,088 total
CA $3,088 total
includes taxes & fees
Image gallery for Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
1010 out of 10 rating
Exceptional
(34 reviews)
Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
Toano, VA
10% off
Price is CA $410
CA $410
CA $3,870 total
CA $3,870 total
includes taxes & fees
Image gallery for Cozy Cabin Getaway with Beautiful Sunsets on York River, minutes from Yorktown
9.89.8 out of 10 rating
Exceptional
(391 reviews)
Cozy Cabin Getaway with Beautiful Sunsets on York River, minutes from Yorktown
Gloucester Point, VA
10% off
Price is CA $217
CA $217
CA $1,855 total
CA $1,855 total
includes taxes & fees
Image gallery for Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
9.89.8 out of 10 rating
Exceptional
(138 reviews)
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!
Williamsburg, VA
10% off
Price is CA $133
CA $133
CA $1,396 total
CA $1,396 total
includes taxes & fees
Image gallery for TOWN + COUNTRY 4 BR House on Capital Trail - Charles City, Williamsburg
9.89.8 out of 10 rating
Exceptional
(29 reviews)
TOWN + COUNTRY 4 BR House on Capital Trail - Charles City, Williamsburg
Williamsburg, VA
10% off
Price is CA $446
CA $446
CA $4,022 total
CA $4,022 total
includes taxes & fees
Image gallery for Historic B&B located walking distance to the Williamsburg and The College of W&M
1010 out of 10 rating
Exceptional
(43 reviews)
Historic B&B located walking distance to the Williamsburg and The College of W&M
Williamsburg, VA
20% off
Price is CA $1,440
CA $1,440
CA $12,485 total
CA $12,485 total
includes taxes & fees
Image gallery for Williamsburg Vacation Villages 4BR, 4BA
8.88.8 out of 10 rating
Excellent
(5 reviews)
Williamsburg Vacation Villages 4BR, 4BA
Williamsburg, VA
33% off
Price is CA $290
CA $290
CA $2,640 total
CA $2,640 total
includes taxes & fees
Image gallery for Tour Historic Gloucester Courthouse - walk to Main Street!
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Tour Historic Gloucester Courthouse - walk to Main Street!
Gloucester, VA
5% off
Price is CA $190
CA $190
CA $1,718 total
CA $1,718 total
includes taxes & fees
Image gallery for Perfect for long-term workers & short stays—comfort, style & convenience await!
8.48.4 out of 10 rating
Very good
(16 reviews)
Perfect for long-term workers & short stays—comfort, style & convenience await!
Gloucester, VA
10% off
Price is CA $219
CA $219
CA $2,123 total
CA $2,123 total
includes taxes & fees
Image gallery for Renovated 3BR home across from Williamsburg Winery with great outdoor space!
1010 out of 10 rating
Exceptional
(17 reviews)
Renovated 3BR home across from Williamsburg Winery with great outdoor space!
Williamsburg, VA
10% off
Price is CA $589
CA $589
CA $5,335 total
CA $5,335 total
includes taxes & fees
Image gallery for Gorgeous River Views/Private Beach - Peaceful Country Home close to Williamsburg
1010 out of 10 rating
Exceptional
(138 reviews)
Gorgeous River Views/Private Beach - Peaceful Country Home close to Williamsburg
Surry, VA
10% off
Price is CA $477
CA $477
CA $4,054 total
CA $4,054 total
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Jamestown Settlement
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Find the best place to stay - Jamestown Settlement
Enjoy our Colonial Style Resort in Williamsburg with Free parking, pool access, mini golf and tennis
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
272 reviews(272 reviews)
Private Cottage on Horse Farm in Williamsburg!
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Private Beach & Pier - James River Beach Cottage - Jamestown & Williamsburg
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
The Cracker Jack House: A Military Salute & Arcade!
Sleeps 12 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Uncle Bill's Lodge & Soccer Pool Showdown
Sleeps 12 · 3 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
King’s Creek Resort by Spinnaker
Sleeps 6 · 2 bedrooms
8.68.6 out of 10
Excellentexcellent
76 reviews(76 reviews)
Top rated rentals - Jamestown Settlement
Excellent Experience
1010 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Panorama james river
1010 out of 10
Exceptionalexceptional
197 reviews(197 reviews)
Thanks Jaymie and Mike
1010 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value