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Vacation Rentals in Southampton County

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Top Vacation Rentals in Southampton County

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

9.8 out of 10, Exceptional, (33)
"Great little home "
The price is ¥16,615
¥23,688 total
includes taxes & fees
Jul 27 - Jul 28
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

The "KINGSDALE" 2 Bedrooms

10.0 out of 10, Exceptional, (5)
"The property felt like my home! Absolutely wonderful! I will be back! 😊"
The price is ¥26,473
¥40,346 total
includes taxes & fees
Jul 28 - Jul 29
The "KINGSDALE" 2 Bedrooms

The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

10.0 out of 10, Exceptional, (59)
"This was a great rental! Clean, well-furnished and fun. It was quiet and comfortable but close to downtown and busch gardens for xmastown!"
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

Relax And Reconnect With Expansive Views Of The Historic James River

10.0 out of 10, Exceptional, (51)
"Lovely stay in a well-appointed home. Perfect for a group, family, or couple."
Relax And Reconnect With Expansive Views Of The Historic James River

History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

10.0 out of 10, Exceptional, (134)
"A group of 9 of us stayed. We enjoyed the historical vibes and secluded peaceful setting. Host was very responsive to questions. "
History, Art, Nature. Built in 1760, 110 Acres of Ancient Woodland Preserve

ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

9.8 out of 10, Exceptional, (241)
"Have an amazing time unwinding!!"
ANALOG - Private Beach & Acres of exclusive sanctuary set in a peaceful forest

Renovated 3BR home across from Williamsburg Winery with great outdoor space!

10.0 out of 10, Exceptional, (16)
"This house is perfect for a visit to Jamestown and Williamsburg. The interior is modern and clean, and we had a wonderful stay! "
Renovated 3BR home across from Williamsburg Winery with great outdoor space!

Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

10.0 out of 10, Exceptional, (120)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Busch Gardens-Williamsburg-Fishing-Cornhole-Deck-River View- FIRE TABLE!

9.6 out of 10, Exceptional, (40)
"Our trip was wonderful, and the rental home exceeded our expectations. It was a perfect fit for my large family, and everyone truly enjoyed their stay. The home was clean, well-stocked, and incredibly comfortable.We especially appreciated the thoughtful touches—upon arrival.The children also had a fantastic time riding the ferry—it was a highlight of the trip.The home was beautiful and we hope to return in the future!"
Busch Gardens-Williamsburg-Fishing-Cornhole-Deck-River View- FIRE TABLE!

Gorgeous model single family home, fully renovated and ready for you.

The price is ¥46,522
¥108,339 total
includes taxes & fees
Jul 28 - Jul 29
Gorgeous model single family home, fully renovated and ready for you.

Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area

9.8 out of 10, Exceptional, (68)
"The cottage is obviously well cared for. Its location is great - right next to the river ferry - and the small beach is a great place to relax. Homeowner was very attentive to every need."
Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (197)
"Great place and location "
Beachfront House on James River. Near Historic Jamestowne and Williamsburg

The Cracker Jack House: A Military Salute & Arcade!

9.4 out of 10, Exceptional, (13)
"Our stay was excellent. We really enjoyed the game room and firepit. The house was very clean and comfortable. We also had lots of fun listening to music on the jukebox. "
The Cracker Jack House: A Military Salute & Arcade!

James River Waterfront with spectacular views across the river from Williamsburg

10.0 out of 10, Exceptional, (136)
"Lovely house with beautiful sunrise. Close to attractions but away from hustle and bustle of big city."
James River Waterfront with spectacular views across the river from Williamsburg

The Great Gatsby: Pink Flamingo Lounge Retreat!

2.0 star property
9.0 out of 10, Wonderful, (8)
"The property was clean and well-maintained, and in a convenient location near Williamsburg, Smithfield and other historic locations. Access to the Jamestowne-Scotland ferry was great."
The Great Gatsby: Pink Flamingo Lounge Retreat!

Dock & Kayaks: Lakefront Roanoke Rapids Home

10.0 out of 10, Exceptional, (29)
"Great location enjoyed our stay."
Dock & Kayaks: Lakefront Roanoke Rapids Home

Large House/8 beds/ Pool table

3.4 out of 10, (3)
"The property was filthy! The carpets were stained there was foreclosure as well as abandoned/vacant property tag the washer had stagnant water in it where there was an awful Oder when try to crime on water went everywhere. Trash all outside the house and under carport. Lawn had not been maintained could not go outside in backyards room had trash from previous tenants also showers backed up when contacting the host response either was delayed or issue never addressed once we told them about...
The price is ¥8,714
¥33,211 total
includes taxes & fees
Aug 4 - Aug 5
Large House/8 beds/ Pool table

Uncle Bill's Lodge & Soccer Pool Showdown

8.6 out of 10, Excellent, (8)
"The home was very comfortable for 5 of us with room to spare. Located in a friendly small town. Many extras included. There are many activities for kids. Our grandchildren had a great time, they would have liked to just stay at the property!. The ferry to Jamestown is very convenient and there is much to see on that side. We also visited the town of Smithfield which is only 20 minutes away. We were looking for a nice slow and relaxing pace and found it. "
Uncle Bill's Lodge & Soccer Pool Showdown

King Suite Retreat with private Pool cottage home Smithfield Virginia

King Suite Retreat with private Pool cottage home Smithfield Virginia

Charming 2800 sq.ft 4-bedroom home with AC and WiFi in Suffolk

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was spotless! Great linens, tvs in every room. We went here for business and the house was 100x better than a hotel. "
Charming 2800 sq.ft 4-bedroom home with AC and WiFi in Suffolk
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.
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Top Southampton County Hotel Reviews