
Diamond Hill vacation rentals
We found 62 vacation rentals — enter your dates for availability
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Diamond Hill
Slopeside Wintergreen - Modern Luxury Ski-In / Ski-Out Condo - Sleeps 8
Sleeps 8 · 2 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Walk to activities / Slopeside! Gated community.
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Beautifully Renovated
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
150 reviews(150 reviews)
2 minutes from the shops and activities; Cozy 1 bedroom end unit.
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
Diamond Hill Studio 09 with Wintergreen Advantage
Sleeps 2 · 1 bedroom · 1 bathroom
Ski-In/Ski-Out Wintergreen Resort Condo w/ Patio!
Sleeps 15 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Top rated rentals - Diamond Hill
Fabulous Wintergreen Stay!
1010 out of 10
Exceptionalexceptional
171 reviews(171 reviews)
Bunk movie room was such a plus for our 4 kids! View off the deck and quick walk to everything can’t be beat. Property very well taken care off!
Clara K.
Stayed Jul 2025
Lovely getaway
1010 out of 10
Exceptionalexceptional
1 review(1 review)
We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay!
Cena H.
Stayed Jul 2025
Weekend Get Away
1010 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
We needed a place to stay after visiting local wineries and breweries with friends. This was great and could walk to restaurants! Place was clean and well stocked!
Lisa B.
Stayed Jun 2025
Relaxing and quiet
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple trip, the full kitchen is an added bonus as well. We would stay again!
Madison D.
Stayed May 2025
Weekend Getaway
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Property is in a great location to relax and enjoy the mountains. The owners have thought of everything to make the stay as convenient as possible! 10 out of 10
Jeff W.
Stayed May 2025
Ski in / Ski Out Massage Chair!!
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
The nicest places we’ve stayed. Ski in / ski out. Walkable to entire village. That massage chair was a dream
Dave S.
Stayed Mar 2025
Great condo!
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
We have stayed here several times and love it! Great updated property and with fully equipped kitchen. The owners are very easy to work with, and the location is perfect for ski in/ski out with minimal stairs.
Julie S.
Stayed Feb 2025
Great experience
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Owners were great and great communication.
Charles N.
Stayed Feb 2025
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value