Find hotels with pools in Chestnut Springs, Roseland from $355

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Check availability on Chestnut Springs Hotels with a Pool

Top Chestnut Springs Hotels with a Pool

Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room
Terrace/patio

Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room

10.0 out of 10, Exceptional, (13)
"We enjoyed the space, amenities and location!"
$396 nightly
The price is $445
Oct 15 - Oct 16
Total with taxes and fees
Wintergreen Retreat: Cabin with Hot Tub, Nestled in Woods, Hiking, Game Room
4 BR cabin mins to trails & breweries pets welcome
Property grounds

4 BR cabin mins to trails & breweries pets welcome

9.6 out of 10, Exceptional, (28)
"Perfect location and a great house "
$537 nightly
The price is $603
Nov 11 - Nov 12
Total with taxes and fees
4 BR cabin mins to trails & breweries pets welcome
Highridge Court 24 with Wintergreen Advantage
Pool

Highridge Court 24 with Wintergreen Advantage

8.0 out of 10, Very Good, (1)
"Nice place with a great view. Take your own Keurig machine though."
$316 nightly
The price is $355
Oct 20 - Oct 21
Total with taxes and fees
Highridge Court 24 with Wintergreen Advantage
Highridge Place 43 with Wintergreen Advantage
Pool

Highridge Place 43 with Wintergreen Advantage

$319 nightly
The price is $359
Oct 22 - Oct 23
Total with taxes and fees
Highridge Place 43 with Wintergreen Advantage
Three Ridges 64 With Wintergreen Advantage
Pool

Three Ridges 64 With Wintergreen Advantage

$378 nightly
The price is $425
Oct 19 - Oct 20
Total with taxes and fees
Three Ridges 64 With Wintergreen Advantage
Highridge Court 08 with Wintergreen Advantage
Pool

Highridge Court 08 with Wintergreen Advantage

2.0 star property
$448 nightly
The price is $503
Nov 4 - Nov 5
Total with taxes and fees
Highridge Court 08 with Wintergreen Advantage
Wintergreen 5BR with Hot Tub, Sauna, Firepit
Terrace/patio

Wintergreen 5BR with Hot Tub, Sauna, Firepit

10.0 out of 10, Exceptional, (4)
"Loved that everything was provided! We were very appreciative of the shampoo, soap, body wash, paper towels and toilet paper provided. It was all good quality and sufficient for our entire stay. We had a great stay!"
$964 nightly
The price is $1,083
Oct 15 - Oct 16
Total with taxes and fees
Wintergreen 5BR with Hot Tub, Sauna, Firepit
Three Ridges 05 With Wintergreen Advantage
Indoor pool

Three Ridges 05 With Wintergreen Advantage

$448 nightly
The price is $503
Oct 19 - Oct 20
Total with taxes and fees
Three Ridges 05 With Wintergreen Advantage
New Build! Log Cabin with Hot Tub in Wintergreen
Terrace/patio

New Build! Log Cabin with Hot Tub in Wintergreen

10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
$1,144 nightly
The price is $1,284
Oct 16 - Oct 17
Total with taxes and fees
New Build! Log Cabin with Hot Tub in Wintergreen
Highridge Court 30 with Wintergreen Advantage
Pool

Highridge Court 30 with Wintergreen Advantage

$319 nightly
The price is $359
Oct 19 - Oct 20
Total with taxes and fees
Highridge Court 30 with Wintergreen Advantage
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 Chestnut Springs Hotel Reviews

Hotel 24 South

Hotel 24 South

10/10 Excellent
"Very nice, quiet, comfortable room. Town and restaurants were walkable and breakfast was great"
Theresa 2-night trip
Posted 5 days ago
Hotel 24 South

Frequently asked questions

What are some hotels with pools in Chestnut Springs?
New Build! Log Cabin with Hot Tub in Wintergreen: Features complimentary wireless internet access, a communal pool, and kitchens. Modern Luxury Mountain Home within Wintergreen Retreat Collection: Vacation home, 1-minute walk from Wintergreen Resort. Offers complimentary wireless internet access, a communal pool, and kitchens. 4 BR cabin mins to trails & breweries pets welcome: Vacation home, 1-minute walk from Wintergreen Resort. Provides kitchens, a communal pool, and Smart TVs. Hotel 24 South: Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Motel 6 Staunton, VA: Features daily, a seasonal outdoor pool, and free self parking.
What is there to see and do in Chestnut Springs?
Make a point to visit attractions like Sherando Lake Recreation Area and Wildlife Center of Virginia. Discover sights such as Wintergreen Resort during your stay.
When is the best time to book a hotel with a pool in Chestnut Springs?
You may want to consider a place to stay that has an outdoor pool if you're planning to visit in the hottest months of July, August, or June when the average temperature is 73°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 38°F.

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