Diamond Hill holiday homes
We found 62 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Diamond Hill
Showing deals for:7 Nov - 14 Nov
Image gallery for Dobie condo
9.69.6 out of 10 rating
Exceptional
(64 reviews)
Dobie condo
Wintergreen, VA
8% off
Price is NZ$4,167
NZ$4,167
NZ$595 per night
includes taxes & fees
Image gallery for Slopeside Wintergreen - Modern Luxury Ski-In / Ski-Out Condo - Sleeps 8
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Slopeside Wintergreen - Modern Luxury Ski-In / Ski-Out Condo - Sleeps 8
Nellysford, VA
14% off
Price is NZ$3,525
NZ$3,525
NZ$504 per night
includes taxes & fees
Image gallery for Ski-In/Ski-Out Wintergreen Resort Condo w/ Patio!
1010 out of 10 rating
Exceptional
(13 reviews)
Ski-In/Ski-Out Wintergreen Resort Condo w/ Patio!
Wintergreen, VA
10% off
Price is NZ$3,933
NZ$3,933
NZ$562 per night
includes taxes & fees
Image gallery for Stylish-Updated-Central -Walk to Slopes-Dogs OK!
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Wintergreen, VA
7% off
Price is NZ$2,329
NZ$2,329
NZ$333 per night
includes taxes & fees
Image gallery for Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
1010 out of 10 rating
Exceptional
(5 reviews)
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Wintergreen, VA
7% off
Price is NZ$2,374
NZ$2,374
NZ$339 per night
includes taxes & fees
Image gallery for Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
Wintergreen, VA
16% off
Price is NZ$1,709
NZ$1,709
NZ$244 per night
includes taxes & fees
Image gallery for Wintergreen Condo -Steps to Ski and restaurants
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Wintergreen Condo -Steps to Ski and restaurants
Wintergreen, VA
7% off
Price is NZ$1,835
NZ$1,835
NZ$262 per night
includes taxes & fees
Image gallery for New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂
9.69.6 out of 10 rating
Exceptional
(10 reviews)
New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂
Wintergreen, VA
8% off
Price is NZ$6,284
NZ$6,284
NZ$898 per night
includes taxes & fees
Image gallery for Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
1010 out of 10 rating
Exceptional
(321 reviews)
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen, VA
7% off
Price is NZ$1,696
NZ$1,696
NZ$242 per night
includes taxes & fees
Image gallery for Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK
9.89.8 out of 10 rating
Exceptional
(179 reviews)
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK
Nellysford, VA
16% off
Price is NZ$3,244
NZ$3,244
NZ$463 per night
includes taxes & fees
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Find the best place to stay - Diamond Hill
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Walk to activities / Slopeside! Gated community.
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Dobie condo
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Dobie 54 with Wintergreen Advantage
Sleeps 6 · 3 bedrooms · 3 bathrooms
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Best True "Ski-In, Ski-Out" 2 Bedroom Condo at Wintergreen, Beautiful, like new.
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value