Holiday rentals in Middlebrook

Entire Country Cottage guesthouse / Very Private

Gloriously private without feeling secluded, this charming guesthouse was totally updated in 2019. Enjoy the peace and quiet. Go for a walk or bike ride on the 28 plus acres or pretty rural lanes. 2.5 miles away is Lake Robertson for activities . Sit on the porch too! On a snowy night, enjoy the wd-burning fireplace . (We will often leave fireplace prepared to light. Gas heating also). Get cozy with the full kitchen, washer/dryer, games and books. DirecTv in the living room and bedroom. too!

Sunrise Casita: a tiny house at Cana Barn

Our 250 sq ft tiny house was built by our talented craftswoman Kara. We used wood from our property and reclaimed materials to create a cozy and unique getaway. The front porch looks out to a beautiful view of the Blue Ridge Mountains and looks up to a local vintage sign. We are LGBTQ+ welcoming. Sunrise to us is the embodiment of a fresh start and a new opportunity. It is hope and possibility, adventure and inspiration, beauty and wonder. We hope all of this for your stay in our tiny house!

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

The Laurel Hill Treehouse

Tucked away in the woods, this Scandinavian-inspired treehouse is a quiet, peaceful spot designed for a relaxed couples getaway. Surrounded by trees and overlooking beautiful woodland views, it’s an easy place to slow down and unwind. Spend your time on the wraparound porch, soak in the hot tub, cool off in the creek, or settle in by the fire at night. This is a serene, comfortable retreat where you can reset, enjoy all that nature has to offer, and simply be present.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

Big Blue #1: Spacious&Modern. Close to Downtown

We welcome you to come stay with us while visiting our small town of Staunton. The Big Blue House #1 is on the 1st floor in a Up/Down Duplex with ample parking. This century home has been updated but still has it's old fashion feel. We are in a central location in Staunton. Just minutes from our lovely downtown. Whether you are visiting Staunton, visiting family or on a work trip. Come enjoy your stay at this conveniently located, spacious and modern unit.

Travelers Nook - close to downtown

The TRAVELERS NOOK is a cute, cozy, one bedroom apartment close to downtown Staunton! It’s located on the second floor, with a private entrance. It has all the charm that you would expect to find in a cute studio apartment! Built by a local architect Tj Collins in the 1920’s. This quaint space has everything you need to enjoy your stay here in Staunton! We do accept small pets on approval with a pet cleaning charge.

Walker's dream. Close to downtown.

Centrally located near the library, Gypsy Hill Park, and downtown Staunton, our private, walkout basement apartment has individually controlled heating and air conditioning. It includes a brick patio, private rear entrance and historic details from the late 1800's. It is generally quiet, but you may sometimes hear the two adults upstairs. Come enjoy this peaceful and centrally-located space.

The Storefront: Downtown Staunton + Unique Stay

Welcome to The Storefront: A Very Small Hotel. The Storefront is located right in the heart of downtown Staunton. The Storefront was built in the early 1900's and was previously a tea shop before becoming a vacation destination. It's like having your own little townhouse in the heart of Staunton's historic district! Keep your car parked and walk everywhere you need to go.

The Stable

Our guesthouse is located in the historic Tree Streets Neighborhood of Waynesboro, VA, an official Appalachian Trail town, located at the southern end of the Shenandoah National Park. We've aptly named the guesthouse "The Stable" because it was originally built and functioned as a stable. It has since been converted into a cozy cottage for guests.

Whimsical Creekside Cabin

Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the wrap around deck, or delight in exploring your own 7 acres in the forest. Our cabin is a cheerful, clean, and private cottage to come home to- or spend your days on property splashing in the creek and sitting out by the fire pit.

The Firefly Springhouse

Private cabin, with bath, located in a quiet country setting, close to town and easy access to two Interstate highways. Comfy queen bed, Climate control with state of the art Trane system. Mini-fridge, microwave, and Keurig coffee maker are included. High speed wireless internet and basic cable TV. All varieties of people are welcome here.