Holiday houses in Prospect

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Top-rated holiday rentals in Prospect

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Condo in Wintergreen Resort

4.78 out of 5 average rating, 67 reviews

Wintergreen Best location,Arcades,king bed,2 room

Enjoy this beautifull newly renovated condo in the 18th hole of wintergreen resort entirely to yourself, cozy, centrally located dont miss this unique stay, within minutes of the slopes. Be pampered with a morning Coffee or hot cocoa in the new granite kitchen with new appliances and relax in the amazing view in the terrace peaceful, surrounded with trees and birds. Sleep really well with all new memory foam mattress, central a/c, heating, fully equipped, 2 Smart Tvs and 2 Arcades NBA and Pacman

Guest favourite

Cottage in Covesville

5 out of 5 average rating, 112 reviews

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Guest favourite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 117 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Guest favourite

Cottage in Powhatan

4.9 out of 5 average rating, 136 reviews

Evening breeze cottage, nestled in the woods

Experience the perfect blend of comfort, tranquility, and tradition in this beautifully maintained home, steeped in a rich heritage of faith and family. Whether you're seeking a peaceful, cozy retreat to unwind or a welcoming base during your time in the area, this home provides an inviting atmosphere where you can truly relax. With its warm, quiet ambiance and pristine cleanliness, it offers an ideal sanctuary for both short stays and longer visits, ensuring your stay is restful and memorable.

Guest favourite

Home in Roseland

5 out of 5 average rating, 9 reviews

Hot Tub! Wintergreen Resort!

Check out our 5 star reviews on VRBO and "cozy cabin at wintergreen dot com". Prepare to escape and relax at our three bedroom, two bath cabin, nestled atop the Blue Ridge mountains, a short walk (5 Houses) to the Devils Knob Overlook. This luxury resort retreat is perfect for couples getaway, wedding, family vacation or girls weekend. Spend the day brewery hopping down the famous Route 151, where you have over twelve wineries and breweries to visit. Or enjoy hiking, skiing, spa & golfing.

Guest favourite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 122 reviews

1 bedroom condo walk to the slopes in 5 min

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the pool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace (wood provided) flat screen TV w/ streaming channels

Superhost

Home in Wintergreen Resort

4.87 out of 5 average rating, 102 reviews

Walk to Ski! HotTub PoolTable Shuffleboard Dogs OK

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

Superhost

Condo in Wintergreen Resort

4.88 out of 5 average rating, 160 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Comfortable 3-BR, 2-bath condo on Devil's Knob Golf Course. Comfortably sleeps 6-7, 2 Queen beds, 1 full bed, futon, & comfy couch. Woodburning fireplace; balcony, small newly renovated kitchen w/stove, dishwasher, microwave, Keurig, tea kettle,coffee maker, crockpot; Smart TV w/ Streaming apps(free only); Walking distance to hiking trails, nature center, DeVine Wine & Coffee shop, tennis facilities, & the lovely wintergreen spa; less than 1 mile from Mountain Inn & restaurants & shops.

Guest favourite

Condo in Wintergreen Resort

4.94 out of 5 average rating, 126 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Guest favourite

Home in Wintergreen Resort

4.94 out of 5 average rating, 54 reviews

4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

4min dive to slopes! Impressive 3-story mountain estate. Ideal for family retreats and adventurous getaways. Features HOT TUB. Wineries, breweries, farmers market, and walk to hiking trails. ★Comfortably sleeps 10: K, K, Full, Twin bunk beds, Sleeper sofa in loft ★Great room with stone fireplace ★Dining table for 8 ★FAST Wi-Fi ★Two 52" HDTVs ★Wrap around decks ★Fire Pit ★Hot Tub ★Plenty of parking Seasonal outdoor pool/tennis access. Resort access not included.

Guest favourite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 125 reviews

Slope side+Panoramic Mountain Views!

Panoramic views over Diamond Hill Ski Slope and the Blue Ridge Mountains. 2 bedroom/2 bath condo. Walk to slopes, hiking trails, and restaurants. Master w/King bed and attached bath with jetted tub. 2nd bedroom hosts 2 bunks- Twins over Double beds. Hall bath with shower and tub. Living Room with sleeper sofa, TV, and wood burning fireplace, wood included! Gated parking lot. Breathtaking Mountain Views + walking distance to the Mountain Inn! Perfection!

Guest favourite

Home in Wintergreen Resort

5 out of 5 average rating, 23 reviews

5-star Luxury 4BR/4BA Lodge w/ HotTub!

Rustic, 5-star lodge great for a Guys or Gals weekend, weddings and family gatherings. Well-appointed with 4 cozy bedrooms each with their own private en suite bathroom. Unleash your inner chef in the gourmet kitchen w/ sun-filled dining area. Spread out in the 2-story family room with gas fireplace. Head outside to the expansive deck overlooking the 14th hole on Devils Knob golf course and enjoy the hot tub and firepit.

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