Esmont Holiday Rentals

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Holiday Rentals in Esmont

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (293)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
The price is NZ$420
includes taxes & fees
30 Sept - 1 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

9.8 out of 10, Exceptional, (159)
"Cute cottage, clean, very convenient location. Everything we needed!"
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is NZ$1,236
includes taxes & fees
27 Oct - 28 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is NZ$415
includes taxes & fees
30 Sept - 1 Oct
The Modern Mountain Condo

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (49)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (53)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

Loveshack, a charming tiny house on a 5 acre farm

9.6 out of 10, Exceptional, (7)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is NZ$452
includes taxes & fees
30 Sept - 1 Oct
Isolated cottage with good view close to many winery and Brewers.

Downtown Carriage House | 1 BR Loft close to the historic downtown mall

9.4 out of 10, Exceptional, (77)
"Great Quite getaway near down town"
Downtown Carriage House | 1 BR Loft close to the historic downtown mall

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (136)
"Very clean place and very accommodating host"
The price is NZ$426
includes taxes & fees
30 Sept - 1 Oct
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

10.0 out of 10, Exceptional, (119)
"This is the perfect location, very clean, fabulous hosts, and nice, quiet neighborhood."
The price is NZ$420
includes taxes & fees
1 Oct - 2 Oct
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

9.0 out of 10, Wonderful, (120)
"Close to good food and attractions in the area. Monticello, Trump Winery, Downtown CVille. "
The price is NZ$365
includes taxes & fees
30 Sept - 1 Oct
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Lotus View Retreat in Yogaville, Chalet with WiFi and AC

10.0 out of 10, Exceptional, (4)
"The view really is that beautiful! It's rural and peaceful! The check-in and check-out was easy and the owners pleasant to work with. The house is very comfortable and open."
The price is NZ$469
includes taxes & fees
30 Sept - 1 Oct
Lotus View Retreat in Yogaville, Chalet with WiFi and AC

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (62)
"House was very nice. Great set up for family."
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (60)
"Loved staying here!"
The price is NZ$599
includes taxes & fees
30 Sept - 1 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (16)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
The price is NZ$485
includes taxes & fees
30 Sept - 1 Oct
Mechum Hill Cottage: Central to Crozet & Cville

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Esmont Hotel Reviews

Find out more about Esmont

Find out more about Esmont

Everything you need to know about Esmont holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Esmont holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Esmont holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Esmont holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Esmont. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Esmont holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Esmont holiday rentals we have selected for you start as low as NZ$365 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Esmont rentals

At Expedia, we put the best Esmont holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Esmont rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Esmont holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Esmont. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Esmont?

Yes, there are holiday rentals close to the most popular sights in Esmont, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Esmont has to offer?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This holiday home rental outside of Esmont is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Esmont?

James River and Simpson Park are a couple of lovely local spots to get outside and enjoy nature. Caromont Farm and Walton's Mountain Museum are a couple of places you'll find in the wider area.

What are holiday rentals like in Esmont?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Esmont. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a small group gathering.