Location - Location - Location! In the heart of Downtown and nestled at the back of the main residence, Sienna Cottage at The Shire 255 is the perfect home away from home for your next trip to Southern Pines. Fully equipped kitchen, spacious living room and table for four, this property can sleep up to four guests. Enjoy easy access from the blue stone gravel drive, as well as dedicated parking for Airbnb guests conveniently located behind the main home - with plenty of auxiliary parking if you have more than one vehicle, and street parking available in case you need it.
Sienna is the perfect retreat for couples or traveling professionals looking to be in a lively and walkable area. When we say walking distance from downtown, we mean it! Below are a few of our favorite local spots worth checking out.
- 400` to The Jefferson Inn (live music on the weekends) - 0.2 miles to Southern Pines Brewing Company (frosé and local beer on tap) - 0.2 miles to Ashtens - 0.2 miles to The Bell Tree Tavern - 0.3 miles to Southern Pines Growler - 0.3 miles to So Pines Pizza - 0.4 miles to Southern Prime Steakhouse (fancy dinner) - 0.7 miles to Betsy`s Crepes (the best breakfast spot around, in our humble opinion) - 0.9 miles to Sly Fox (the butter chicken dish is to die for - don`t take my word for it) - Carolina Horse Park Foundation (12.7 miles) - The list goes on and on...
EV Charging is available just a short walk (0.2 miles) from the property at the Southern Pines Library.
The Shire 255 is managed by Stay Well Vacation Rentals, a locally owned company offering a personalized experience and deep knowledge of the area. We live and work right here in Moore County and love interacting with our guests. As local Realtors, we`re happy to offer insights or recommendations about the area. Feel free to reach out anytime – we`re just a message away! Out of respect for other guests and due to shared walls in The Shire 255, pets are not allowed. Any unauthorized pets will incur a $250 fee. Please check Unit D, a detached cottage, availability for all reservations with pets including service animals.
Our prices include all fees. No hidden fees.
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Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Parking available
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Out of respect for other guests and due to shared walls in The Shire 255, pets are not allowed. Any unauthorized pets will incur a $250 fee.
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Southern Pines
Located in Southern Pines, this apartment is in the city centre. Southern Pines Golf Club and Pine Needles Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Weymouth Woods-Sandhills Nature Preserve and Reservoir Park. Malcolm Blue Farm and Hillcrest Park are also worth visiting.
Weymouth Woods-Sandhills Nature Preserve - 15 min walk - 1.3 km
Campbell House Galleries - 15 min walk - 1.3 km
Southern Pines Golf Club - 2 min drive - 1.6 km
Getting around
Southern Pines Station - 4 min walk
Restaurants
Chapman's Food and Spirits - 5 min walk
Busaba Cafe - 3 min walk
Betsy's Crepes - 6 min walk
Hatchet Brewing Compan - 12 min walk
Red’s Corner - 20 min walk
Frequently asked questions
Is Sienna at The Shire 255 - Unit B - Downtown! pet-friendly?
No, only service animals are welcome at the property.
How much does it cost to stay at Sienna at The Shire 255 - Unit B - Downtown!?
As of 14 Apr 2026, prices found for a 1-night stay for 2 adults at Sienna at The Shire 255 - Unit B - Downtown! on 26 Jun 2026 start from £161, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Sienna at The Shire 255 - Unit B - Downtown!?
On-site parking is available at the property.
What time is check-in at Sienna at The Shire 255 - Unit B - Downtown!?
Check-in begins at 4:00 PM.
What time is check-out at Sienna at The Shire 255 - Unit B - Downtown!?
Checkout is at 10:00 AM.
Where is Sienna at The Shire 255 - Unit B - Downtown! located?
Located in the heart of Southern Pines, this apartment building is within a 10-minute walk of Sunrise Theater and Hyland Hills Golf Club. Campbell House Galleries and Weymouth Woods-Sandhills Nature Preserve are also within 1 mile (2 km). Southern Pines Station is only a 4-minute walk.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Fantastic accommodations! A great place right off downtown…but just far enough away from the hustle & bustle. A cozy and comfortable home away from home. The host was super attentive and made sure we had a great stay. Can’t wait to go back!
Check in was super easy. New appliances in the kitchen and laundry room. Great Wi-Fi! We also got to watch baby birds in their nest on the Wreath hanging on the front door! We loved that it was close to town within walking distance! We would definitely stay here again!
Paula M.
Stayed 4 nights in Jul 2025
Response from VrboOwner on 6 Aug 2025
Paula, thank you for the wonderful 5-star review! We’re so glad you enjoyed the easy check-in, updated appliances, and reliable Wi-Fi. Watching the baby birds is such a sweet bonus! We love that you enjoyed being within walking distance to town. We’d be delighted to host you again at Stay Well!
Great rate, close walking distance to everything. Unit was clean and modern. Major upgrade over a hotel. Perfect setup for a weekend visit.
James A.
Stayed 2 nights in Apr 2025
Response from VrboOwner on 14 Apr 2025
Thanks for the glowing review, James! We’re so glad Sienna at The Shire 255 was the perfect fit for your weekend visit. It’s great to hear you enjoyed the clean, modern space and walkable location—and that it felt like a major upgrade from a hotel! We’d love to welcome you back anytime.
After staying here for her last horse show, my daughter suggested we do it again. Such a convenient location for enjoying the shops & restaurants in SoPi and for me to grab a morning run. Everything you need & spotless. 20 minutes to Carolina Horse Park.
Joy S.
Stayed 3 nights in Oct 2024
Response from VrboOwner on 11 Apr 2025
Thank you so much for the kind review! We love hearing that your daughter wanted to stay again—that’s the best compliment. We’re glad the location worked well for both the show and your morning runs, and that everything was spotless and just what you needed. We’d be happy to host you again anytime you’re back for another horse show or SoPi getaway!
Unit B was nicely decorated. The reason for my rating was because the shower was too short for me. It's less private than I thought as well. It has more listings surrounding than just the above unit.
Katlin K.
Stayed 2 nights in Oct 2025
About the host
Hosted by Spartan Property Management
Premier Host
They consistently provide great experiences for their guests