Chestnut Springs holiday homes
We found 283 holiday rentals — enter your dates for availability
Select from 37 houses, 16 flats and other holiday rentals to find the perfect place for your stay in Chestnut Springs. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Chestnut Springs
Showing deals for:18 Jul - 25 Jul
Image gallery for Luxury Designer Home, Dome and Top amenities

1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Home, Dome and Top amenities
Nellysford, VA
8% off
Price is NZ$10,632
NZ$10,632
NZ$1,519 per night
includes taxes & fees
Image gallery for Modern Wintergreen Cabin with Hot Tub, Sauna

1010 out of 10 rating
Exceptional
(23 reviews)
Modern Wintergreen Cabin with Hot Tub, Sauna
Roseland, VA
7% off
Price is NZ$7,831
NZ$7,831
NZ$1,119 per night
includes taxes & fees
Image gallery for Zero step entry- EV charger- 2 King suites

1010 out of 10 rating
Exceptional
(5 reviews)
Zero step entry- EV charger- 2 King suites
Nellysford, VA
8% off
Price is NZ$5,232
NZ$5,232
NZ$747 per night
includes taxes & fees
Image gallery for Golden Tee 60"TV Fireplace Deck Grill Pool Tennis

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
Roseland, VA
7% off
Price is NZ$5,011
NZ$5,011
NZ$716 per night
includes taxes & fees
Image gallery for 180 Degree Breathtaking Views

1010 out of 10 rating
Exceptional
(14 reviews)
180 Degree Breathtaking Views
Nellysford, VA
24% off
Price is NZ$4,324
NZ$4,324
NZ$618 per night
includes taxes & fees
Image gallery for Luxe Private Getaway in the Heart of Wintergreen!

8.48.4 out of 10 rating
Very good
(8 reviews)
Luxe Private Getaway in the Heart of Wintergreen!
Nellysford, VA
7% off
Price is NZ$8,509
NZ$8,509
NZ$1,216 per night
includes taxes & fees
Image gallery for Marley's Cabin - a five star getaway on Wintergreen mountain

1010 out of 10 rating
Exceptional
(69 reviews)
Marley's Cabin - a five star getaway on Wintergreen mountain
Nellysford, VA
8% off
Price is NZ$8,546
NZ$8,546
NZ$1,221 per night
includes taxes & fees
Image gallery for Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly
Nellysford, VA
7% off
Price is NZ$3,389
NZ$3,389
NZ$484 per night
includes taxes & fees
Image gallery for Luxurious Family Friendly Mountain Home! Great Location on Devils Knob

1010 out of 10 rating
Exceptional
(94 reviews)
Luxurious Family Friendly Mountain Home! Great Location on Devils Knob
Nellysford, VA
8% off
Price is NZ$4,223
NZ$4,223
NZ$603 per night
includes taxes & fees
Image gallery for Hiker’s paradise plus NEW HOT TUB!

1010 out of 10 rating
Exceptional
(32 reviews)
Hiker’s paradise plus NEW HOT TUB!
Nellysford, VA
8% off
Price is NZ$8,547
NZ$8,547
NZ$1,221 per night
includes taxes & fees
Image gallery for Spectacular mountain home perfect for multiple families! Just added '80s arcade!

9.69.6 out of 10 rating
Exceptional
(57 reviews)
Spectacular mountain home perfect for multiple families! Just added '80s arcade!
Nellysford, VA
7% off
Price is NZ$3,940
NZ$3,940
NZ$563 per night
includes taxes & fees
Image gallery for Amazing Views! Hot Tub - Gazebo - Pool Table - Arcade - Grill - WIFI - Fireplace

1010 out of 10 rating
Exceptional
(12 reviews)
Amazing Views! Hot Tub - Gazebo - Pool Table - Arcade - Grill - WIFI - Fireplace
Nellysford, VA
8% off
Price is NZ$6,994
NZ$6,994
NZ$999 per night
includes taxes & fees
Image gallery for Kick back at Virginia’s premier ski and golf resort

1010 out of 10 rating
Exceptional
(134 reviews)
Kick back at Virginia’s premier ski and golf resort
Nellysford, VA
9% off
Price is NZ$5,490
NZ$5,490
NZ$784 per night
includes taxes & fees
Image gallery for Wintergreen Resort Home, @ top of mountain with shuttle acces to Ski Lifts

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Wintergreen Resort Home, @ top of mountain with shuttle acces to Ski Lifts
Nellysford, VA
11% off
Price is NZ$3,263
NZ$3,263
NZ$466 per night
includes taxes & fees
Image gallery for 5min to Ski! DogsOK PAC-MAN Fireplace Pack 'n Play

9.69.6 out of 10 rating
Exceptional
(17 reviews)
5min to Ski! DogsOK PAC-MAN Fireplace Pack 'n Play
Nellysford, VA
7% off
Price is NZ$3,481
NZ$3,481
NZ$497 per night
includes taxes & fees
Image gallery for Serene Wintergreen Retreat, Nestled in the Trees

9.69.6 out of 10 rating
Exceptional
(12 reviews)
Serene Wintergreen Retreat, Nestled in the Trees
Nellysford, VA
7% off
Price is NZ$7,797
NZ$7,797
NZ$1,114 per night
includes taxes & fees
Image gallery for Luxury Condo in the Sky! Finest in Wintergreen!

1010 out of 10 rating
Exceptional
(21 reviews)
Luxury Condo in the Sky! Finest in Wintergreen!
Nellysford, VA
8% off
Price is NZ$3,870
NZ$3,870
NZ$553 per night
includes taxes & fees
Image gallery for Whispering Creek Hot Tub Pool TennisGolf King Beds

9.29.2 out of 10 rating
Wonderful
(11 reviews)
Whispering Creek Hot Tub Pool TennisGolf King Beds
Nellysford, VA
7% off
Price is NZ$4,020
NZ$4,020
NZ$574 per night
includes taxes & fees
Image gallery for Dobie condo

9.69.6 out of 10 rating
Exceptional
(59 reviews)
Dobie condo
Wintergreen, VA
8% off
Price is NZ$8,359
NZ$8,359
NZ$1,194 per night
includes taxes & fees
Image gallery for Book Now for Spring and Summer....Awesome Views and 5-Star Amenities

1010 out of 10 rating
Exceptional
(172 reviews)
Book Now for Spring and Summer....Awesome Views and 5-Star Amenities
Nellysford, VA
8% off
Price is NZ$4,535
NZ$4,535
NZ$648 per night
includes taxes & fees
Image gallery for Open floor plan close to skiing, hiking, and dining.

1010 out of 10 rating
Exceptional
(22 reviews)
Open floor plan close to skiing, hiking, and dining.
Nellysford, VA
8% off
Price is NZ$7,218
NZ$7,218
NZ$1,031 per night
includes taxes & fees
Image gallery for Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf
Nellysford, VA
7% off
Price is NZ$3,718
NZ$3,718
NZ$531 per night
includes taxes & fees
Image gallery for Ski-In/Out, Beautiful Mountain & Valley Views

9.89.8 out of 10 rating
Exceptional
(91 reviews)
Ski-In/Out, Beautiful Mountain & Valley Views
Nellysford, VA
12% off
Price is NZ$3,571
NZ$3,571
NZ$510 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
(177 reviews)
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK
Nellysford, VA
16% off
Price is NZ$3,277
NZ$3,277
NZ$468 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chestnut Springs
Hilltop Escape At Wintergreen
Sleeps 14 · 4 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
Stunning newly rebuilt home! Perfect peaceful getaway that sleeps 14!
Sleeps 14 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Golf Course Views Golden Tee Pool Tennis Golf Hike
Sleeps 12 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
Sleeps 14 · 5 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Golden Tee 60"TV Fireplace Deck Grill Pool Tennis
Sleeps 14 · 6 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
Sleeps 11 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 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
Frequently asked questions
What is the most popular type of holiday home accommodation in Chestnut Springs?
Houses are the most popular kind of holiday home in Chestnut Springs, according to our data. Even if you have a different idea about what you’d like, Bookabach has properties in many shapes and sizes. Look over our options to find your perfect fit.
How much does it cost to rent a holiday home in Chestnut Springs?
The average price for a holiday home in Chestnut Springs is determined by several factors, like time of year, length of stay and property type. Whether you prefer a sprawling house with room for friends and family or a cosy cabin just enough for two, just add your dates of travel to find stays with unbeatable value.
How much does it cost to rent a beach house in Chestnut Springs?
The average price for a holiday home near the beach in Chestnut Springs will depend on when you’re going and the size and style of property you want. You can find prices quickly and easily on Bookabach by entering the dates you’ll be travelling. Then use the handy filters to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in Chestnut Springs?
Yes. There are. You’ll have your pick of 57 holiday homes that cater to pets in Chestnut Springs. Many of our pet-friendly holiday homes come with an area outdoors for your furry friend to have fun in, complimentary treats, special dog beds and proximity to parks or green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Bookabach.
Can I rent a house with a pool in Chestnut Springs?
Add a whole new level of fun to your holiday by booking one of the 36 houses with a private pool in Chestnut Springs. Use our search filter to find the kind of property you want on Bookabach, and then spend leisurely days playing and splashing in a swimming pool that’s exclusively for you.
What are popular home amenities in Chestnut Springs?
When it comes to home amenities that people are searching for in Chestnut Springs, mountain views, a nearby river and nearby museums are the most popular. With Bookabach holiday homes, there are options to match your taste and style, whether you’re going away with relatives, friends or even pets.
Are there large group holiday homes in Chestnut Springs?
With 25 holiday homes that can sleep 10 or more guests in Chestnut Springs, you don’t have to keep your invite list short. From fun family holidays to events like weddings and birthday parties, Bookabach can help you find a large group home to suit the occasion.
Are there holiday homes in Chestnut Springs that welcome kids?
Bring the entire group together for a memorable adventure in Chestnut Springs at one of our 57 family-friendly holiday homes. A lot of these stays offer conveniences that are suitable for trips with the kids, including dining rooms, living rooms and entertainment units. Simply check the “Properties good for families” filter and pick your favourite.
What are the top attractions for families in Chestnut Springs?
Have a fun day out with the family at Stoney Creek Golf Course. This top attraction is close to the centre of Chestnut Springs.
Can I find two-bedroom holiday homes in Chestnut Springs?
You can pick from 11 two-bedroom holiday homes in Chestnut Springs. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There’s enough space for whoever’s fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Chestnut Springs?
Chestnut Springs has 27 holiday homes with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming TV shows with the family to writing and sending emails, these Bookabach homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Chestnut Springs?
You’ll have your pick of 53 holiday homes with air conditioning in Chestnut Springs offering that cooling breeze and extra bit of comfort. Enter your preferred dates of travel and then use our handy filter tool to help you book stays with air conditioning.
How old do you have to be to rent a holiday home in Chestnut Springs?
We recommend checking with the Chestnut Springs holiday home you’d like on Bookabach as the age limit differs. However, it’s normally 16, 18 or 21.
How long can I rent a holiday home in Chestnut Springs for?
It all depends on the Chestnut Springs property. To look at a list of options offering extended stays, simply enter your dates and number of guests into Bookabach’s search page. Enjoy having the entire property to yourself, along with home comforts like air conditioning, a kitchen and a yard to run around in. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.