Holiday Rentals in Whispering Pines

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Holiday Rentals in Whispering Pines

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (288)
"Very clean"
The price is €147
includes taxes & fees
29 Nov - 30 Nov
Clear Lake Cottages & Marina

Secluded home with private saltwater pool, spa & amazing view - dog-friendly

8.8 out of 10, Excellent, (21)
"Nice, clean house, great views"
Secluded home with private saltwater pool, spa & amazing view - dog-friendly

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

10.0 out of 10, Exceptional, (153)
"The cottage and the grounds are absolutely gorgeous! We loved the way the cottage was decorated, so cozy! Everything was well appointed. There are multiple places on the grounds to sit and enjoy a glass of wine and the scenery. It is the perfect size for two couples. The location is close to downtown Healdsburg, Dry Creek wineries and a five-minute walk to the Dry Creek General Store! Napa is only a little over an hour away. The owners and property manager responded quickly when we had...
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Cottage home near the Russian River; county parks; numerous wineries

10.0 out of 10, Exceptional, (91)
"The property was very good and met all our needs with a couple of exceptions. The bathroom towels were not good, a little smelly and really need to be upgraded along with the toilet paper!"
Cottage home near the Russian River; county parks; numerous wineries

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

10.0 out of 10, Exceptional, (19)
"We were in Napa Valley for a special event with Truffle Shuffle at the Charles Krug vineyard. This home was in the perfect location to attend our event. Everything was as stated in the listing, and Arturo was very responsive to all our needs. We had one minor issue; he was all over it and corrected it immediately. I highly recommend this location. We had three couples, and this home accommodated us perfectly."
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (39)
"Great place to stay. Conveniently located for our needs."
The price is €221
includes taxes & fees
1 Dec - 2 Dec
Comfort and Style in Our Queen Cottage

Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

10.0 out of 10, Exceptional, (122)
"Casa Loma is a spectacular property. Definitely the best vrbo propert I have experienced."
Casa Loma - THE best Napa Valley Views at an amazing, modern 35 acre estate

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (228)
"a"
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

10.0 out of 10, Exceptional, (143)
"We got our family together to celebrate a 60th birthday at this perfect spot, and as my children described it was Idyllic! Such a comfortable home, the property is so well kept, the location was perfect. The property management was very quick to support us, we appreciate being able to enjoy such a treat!"
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (27)
"Adorable, comfortable, neat and clean. It had everything we needed except a crab claw cracker. Loved the outdoor seating areas, especially the fire pit area. A true home away from home. "
Chalk Hill Cottage Close to Wineries

Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

10.0 out of 10, Exceptional, (23)
"An incredible weekend. We absolutely loved our stay and this was the perfect place for our family to celebrate a big milestone birthday!"
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!

Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries

9.2 out of 10, Wonderful, (88)
"Cleanliness could have been better ( lots of cobwebs and dead flies in the tub) but we enjoyed the property."
Stunning Home with Pool, Hot Tub, Decks, & Gourmet Kitchen - Close to Wineries

Newly Refurbished! Nest Cottage at ru's Farm.

9.8 out of 10, Exceptional, (156)
"This property is exactly as promised. It’s located in such a beautiful area of Healdsburg. If you’re looking for a quiet getaway this is the place for you!"
Newly Refurbished! Nest Cottage at ru's Farm.

Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

9.0 out of 10, Wonderful, (8)
"Very nice location and amenities. Horrible Wi-Fi and TV. Very bad lighting in kitchen area. No wine opener in home so needed to go out and get one. Overall though we enjoyed our stay. "
Gable by AvantStay | Beautiful 3.5 Acre Oasis w/ Gorgeous Views, Pool & Hot Tub

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (38)
"This is the second time that we have stayed at Chanric and we have really enjoyed it both times. It is beautiful, updated, clean, well equipped, and well managed. The property manager was accessible, friendly, and helpful. We have been to Napa with various groups many times, but this is where we will stay on future trips!"
The price is €1,825
includes taxes & fees
3 Dec - 4 Dec
Luxury Napa Estate With Pool/Hot-tub/Concierge

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (55)
"Huge house and the views are incredible along with all the amenities. Alexa was amazing for all our needs! "
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Cobb Mountain Chalet King Size Suite

10.0 out of 10, Exceptional, (13)
"Perfect place to stay, nice and cozy!"
The price is €157
includes taxes & fees
18 Dec - 19 Dec
Cobb Mountain Chalet King Size Suite

Pool heating available!

9.8 out of 10, Exceptional, (28)
"The property was perfect for a weekend getaway with some friends. The outdoor space was beautiful and easily useable. I enjoyed the gardens and the natural beauty of the area. The accommodations were clean and comfortable. I hope to be able to rent this property again "
Pool heating available!

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

10.0 out of 10, Exceptional, (60)
"What a lovely little property! The location was great and a very short drive into town and close to many wineries. We spent every morning sitting out on the cute patio drinking coffee and listening to the birds under the beautiful trees. And it was the best stocked house we have ever stayed in! Great selection of spices for cooking and all the other essentials. Fantastic!"
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

Luxury Estate – Views, Pool, 100 Yard Golf Hole

9.6 out of 10, Exceptional, (15)
"Great property for our group. "
Luxury Estate – Views, Pool, 100 Yard Golf Hole
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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Other types of properties in Whispering Pines you may be interested in

UpValley Inn & Hot Springs, Ascend Hotel Collection

2.5 star property
9.0 out of 10, Wonderful, (797)
"The room and pools were clean and well-equipped. The environment was quiet and we loved the availability of the morning coffee. We had a very nice stay."
The price is €147
includes taxes & fees
16 Dec - 17 Dec
UpValley Inn & Hot Springs, Ascend Hotel Collection

Solage, Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (615)
"Beautiful property. Wonderful restaurants on site. Fire pits, lit up palm trees, pool and hot tub just gorgeous "
The price is €950
includes taxes & fees
12 Dec - 13 Dec
Solage, Auberge Resorts Collection

Mount View Hotel & Spa

3.5 star property
9.0 out of 10, Wonderful, (944)
"Nice place. Grear location "
The price is €200
includes taxes & fees
1 Dec - 2 Dec
Mount View Hotel & Spa
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.

Frequently asked questions

Are there holiday rentals in Whispering Pines?

Yes, there are holiday rentals close to the most popular sights in Whispering Pines, 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 Whispering Pines has to offer?

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views: This holiday home rental outside of Whispering Pines is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private balcony, a private garden and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Whispering Pines?

While exploring the area, visit family-friendly sights like SingleThread Farm at Dry Creek, or get outside and enjoy nature at Cobb Mountain. In the wider area, you’ll find Twin Pine Casino and Redbud Park.

What’s a holiday rental in Whispering Pines like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Whispering Pines. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.