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South Boston Vacation Rentals

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Vacation Rentals in South Boston

2 Mi to South Boston Speedway: Cozy Tiny Home!

3.0 star property
2 Mi to South Boston Speedway: Cozy Tiny Home!

Located in Historic Old West End. Minutes from the River District and Casino.

9.6 out of 10, Exceptional, (23)
"Had a wonderful Sister getaway weekend at the Vintage Charm! The home was perfect for our weekend, so clean and comfortable! Lovely neighborhood with lots to do in the area, we can’t wait to go back!!"
The price is CA $167
CA $361 total
includes taxes & fees
Jul 22 - Jul 23
Located in Historic Old West End. Minutes from the River District and Casino.

Solar powered cottage at lake, with dock, on private 300 acre timber preserve

9.6 out of 10, Exceptional, (154)
"This is an amazing little cabin. Perfect for a couples getaway. We really enjoyed our stay. Very private!!!"
Solar powered cottage at lake, with dock, on private 300 acre timber preserve

Cute Lakefront Cottage

9.8 out of 10, Exceptional, (50)
"Loved how simple is was."
Cute Lakefront Cottage

Walking Distance to Casino

10.0 out of 10, Exceptional, (19)
"This home was great, very clean and well stocked."
Walking Distance to Casino

Hidden Haven - Hot Tub, Outdoor Shower & Firepit

9.6 out of 10, Exceptional, (18)
"Staying here in the off-season was perfection! Surrounded by beautiful trees, the lake, wildlife, and quiet was so relaxing!"
Hidden Haven - Hot Tub, Outdoor Shower & Firepit

Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool POOLS OPEN

10.0 out of 10, Exceptional, (31)
"Always a joy to stay here! We look forward to coming back again some day soon!"
Miles to VIR, Caesar's VA Casino, Martinsv'l , S.Boston, Priv. Pool POOLS OPEN

Kerr Lake waterfront home w/dock, just off main channel, close to town!

2.0 star property
10.0 out of 10, Exceptional, (5)
"This perfectly sized house overlooking a lake, was also convenient to downtown Clarksville. We would definitely stay again!"
Kerr Lake waterfront home w/dock, just off main channel, close to town!

Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

9.6 out of 10, Exceptional, (89)
"Very accommodating house, great spot on the lake"
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

Cozy Lakefront Cabin in Semora w/ Large Dock!

9.8 out of 10, Exceptional, (6)
"Awesome location"
Cozy Lakefront Cabin in Semora w/ Large Dock!

Backwoods Milton House 3BR&2bath 3 Miles from VIR

2.0 star property
9.6 out of 10, Exceptional, (10)
"Loved the location and the house was cute and furnished nicely."
Backwoods Milton House 3BR&2bath 3 Miles from VIR

Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

10.0 out of 10, Exceptional, (180)
"Great accommodations!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

Coleman 202 RD travel trailer. Located on the owner's lakefront property!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed or stay! The camper was perfect for the weekend. Hunter and his family were very nice and accommodating. The camper was well stocked and really clean. "
The price is CA $197
CA $308 total
includes taxes & fees
Jul 22 - Jul 23
Coleman 202 RD travel trailer. Located on the owner's lakefront property!

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (91)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

Cozy cabin w/ hot tub! Lake access w/ walk to pier

9.8 out of 10, Exceptional, (10)
"Beautiful home, enjoyed our family time together!"
Cozy cabin w/ hot tub! Lake access w/ walk to pier

Vacation home just 4 minutes drive to Caesars Virginia Casino

10.0 out of 10, Exceptional, (4)
"Perfect house to get a night out at the casino."
The price is CA $210
CA $401 total
includes taxes & fees
Jul 22 - Jul 23
Vacation home just 4 minutes drive to Caesars Virginia Casino

Renovated 1BR - 3 Block Walk to Casino - Clean, Quiet, Safe & Guest-Favorite

10.0 out of 10, Exceptional, (3)
"As a person who travels alot for work and normally stays in a chain hotel room, I was extremely impressed with this property - it is clean, well appointed, quite comfortable and in a convenient location. I highly recommend this property!!"
Renovated 1BR - 3 Block Walk to Casino - Clean, Quiet, Safe & Guest-Favorite

The Cedar Farm Close To VIR, Danville

10.0 out of 10, Exceptional, (33)
"Our stay was wonderful! The property was as described—clean, comfortable, and well-equipped with everything we needed. The host was responsive and made the check-in process seamless. The location was great, and we had a pleasant and relaxing experience. Would definitely stay again!"
The Cedar Farm Close To VIR, Danville

Single-Story Cabin on Hyco Lake: Swim & Unwind!

8.4 out of 10, Very good, (6)
"The property was as advertised. Therecwere two pro"
Single-Story Cabin on Hyco Lake: Swim & Unwind!

"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks

10.0 out of 10, Exceptional, (170)
"Great views, well appointed and comfy! Loved the beds and linens, the jacuzzi tub, and the PS4! The loft view was stunning and quite romantic on a rainy day. Will definitely be back!!!"
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks
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 South Boston Hotel Reviews

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near North Main Street Park, or you can select a more remote option if you want a relaxing stay. Our travelers say South Boston has a good selection of restaurants. Make sure you have time to check out the local tours and entertainment choices during your trip.

What are some of the best vacation rentals that South Boston has to offer?

Located in Historic Old West End. Minutes from the River District and Casino.: This vacation home rental near South Boston has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in South Boston?

Choose from 3 Expedia vacation rentals in South Boston for a memorable vacation.

What can I see and do in South Boston?

Family-friendly attractions include North Main Street Park and Vaughan St. Park, whereas Hudson Heritage Farms and Constitution Square are a couple of great spots to enjoy the outdoors. Downtown South Boston Farmers Market and South Boston Speedway are other places to visit while you're in town.

What are vacation rentals like in South Boston?

Vacation rentals are privately owned properties you can reserve for a short or long stay in South Boston. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for small groups.