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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!

Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

10.0 out of 10, Exceptional, (94)
"We enjoyed our stay and loved the cabin."
Lakefront Log Cabin on Beautiful Kerr Lake in downtown Clarksville VA

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

9.8 out of 10, Exceptional, (156)
"Great location. Atmosphere. And overall vibe. Cant wait to Hopefully Go Again!"
Solar powered cottage at lake, with dock, on private 300 acre timber preserve

Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

9.8 out of 10, Exceptional, (30)
"Beautiful home, comfortable beds, spacious kitchen/living area. Great location! We plan to book again!"
Bring YOUR BOAT- Private Dock, Deep Water, Gameroom and Firepit

H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa

9.8 out of 10, Exceptional, (93)
"Beautiful location on the lake!!"
H2O-FRONT Chef’s_Kitchen Gig-WiFi DogsOK EV-Charger Alexa

Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!

2.0 star property
9.8 out of 10, Exceptional, (6)
"This perfectly sized house overlooking a lake, was also convenient to downtown Clarksville. We would definitely stay again!"
Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!

Walking Distance to Casino

10.0 out of 10, Exceptional, (23)
"Fantastic two bedroom house, up to date, extremely clean, great televisions, well stocked. Highly recommend! "
The price is CA $263
CA $681 total
includes taxes & fees
Sep 8 - Sep 9
Walking Distance to Casino

Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great getaway place for couples or small families. "
The price is CA $193
CA $243 total
includes taxes & fees
Sep 7 - Sep 8
Log Cabin Retreat/Pet Friendly: Lake, Golf & Wine

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

10.0 out of 10, Exceptional, (183)
"Great accommodations!"
Kerr Lake Log Cabin On Calm Cove With Gentle Slope To Water, Nearby Sandy Beach

Historic 2 br & 2 ba On the River

9.6 out of 10, Exceptional, (41)
"Pleasant experience."
Historic 2 br & 2 ba On the River

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

9.8 out of 10, Exceptional, (27)
"Perfect location to the casino and restaurants. We loved our stay. "
The price is CA $168
CA $361 total
includes taxes & fees
Sep 7 - Sep 8
Located in Historic Old West End. Minutes from the River District and Casino.

Cozy retreat with lots of room for outdoor activities.

10.0 out of 10, Exceptional, (11)
"The place was very nice and clean. "
Cozy retreat with lots of room for outdoor activities.

Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

10.0 out of 10, Exceptional, (2)
"The property was nice and clean. It’s future, three bedrooms, one bathroom, living room, space, laundry area, and kitchen. I rented this home for three nights and it was comfortable. I would stay here again."
The price is CA $206
CA $267 total
includes taxes & fees
Sep 8 - Sep 9
Home featuring 3 Rooms 1 Bath Sleeps 6 Guest

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

10.0 out of 10, Exceptional, (171)
"Absolutely fabulous views of the lake and well furnished both inside and out. Comfortable furniture and excellent mattresses and pillows. Hosts were easy to communicate with and very responsive. We will definitely stay again!"
"Cottage On The Cove" Private Lakefront Paradise with Paddleboards & Kayaks

Historic 2 br & 1 ba On the River

9.6 out of 10, Exceptional, (45)
"This is a lovely property. We gladly recommend to travelers"
Historic 2 br & 1 ba On the River

Vacation home just 4 minutes drive to Caesars Virginia Casino

10.0 out of 10, Exceptional, (5)
"Perfect house to get a night out at the casino."
The price is CA $211
CA $401 total
includes taxes & fees
Sep 7 - Sep 8
Vacation home just 4 minutes drive to Caesars Virginia Casino

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

9.6 out of 10, Exceptional, (90)
"Went with family a friends. Lovely house, two docks were nice just a little bit of a walk to get to them but there was a nice cleared path way to get to them. Would definitely stay again. "
Private dock/beach on quiet cove - Lake house w/ king beds. Pet-friendly

WATERFRONT LOG HOME! HOT TUB/2 FIREPLACES/FIRE PIT/LARGE DECK/77" TV SUR. SOUND!

9.6 out of 10, Exceptional, (70)
"We really enjoyed our stay and liked being so close to the water."
WATERFRONT LOG HOME! HOT TUB/2 FIREPLACES/FIRE PIT/LARGE DECK/77" TV SUR. SOUND!

Cute Lakefront Cottage

9.8 out of 10, Exceptional, (54)
"Great place for our needs. Host is very accommodating. "
Cute Lakefront Cottage

Rustic Red Cabin on Kerr Lake

10.0 out of 10, Exceptional, (1)
"Enjoyed this place...rustic but has lots of great views, comfort and places to chill. Dog friendly, too but don't trust GPS. Go right at dumpster...not left and don't turn on Stuckornot Rd! Honestly, I hated to leave...and the OBX us my home! LolIf you enjoy a woodsy escape, this is your place."
Rustic Red Cabin on Kerr Lake
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

Find out more about South Boston

Find out more about South Boston

Everything you need to know about South Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Boston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Boston vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Boston vacation rentals we have selected for you start as low as CA $168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near Vaughan St. 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?

Kerr/Buggs Island Lake waterfront home w/dock, just off main channel!: This vacation home rental near South Boston is located on a lake and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Vaughan St. Park and North Main Street 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.