A mountainous landscape with dense forests and a rocky cliff.

Round Top Chalets

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Round Top chalets

Outdoor dining

Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (2 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$238 nightly
The price is $253
Jul 28 - Jul 29
Total with taxes and fees
Jessie's Harvest House
Outdoor dining

Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
$180 nightly
The price is $190
Aug 20 - Aug 21
Total with taxes and fees
Jessie's Harvest House Suite
Exterior

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.2 out of 10, Wonderful, (27 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
$200 nightly
The price is $216
Jul 26 - Jul 27
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Outdoor dining

Jessie's Harvest House

Jessie's Harvest House
Tannersville
$238 nightly
The price is $253
Jul 28 - Jul 29
Total with taxes and fees
Jessie's Harvest House
Property grounds

Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors
Hensonville
10.0 out of 10, Exceptional, (3 reviews)
"Great house and great host! Very convenient location particularly to Windham Mountain. "
United States
Kyrill A.
$580 nightly
The price is $627
Jul 26 - Jul 27
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors
Outdoor dining

Jessie's Harvest House

Jessie's Harvest House
Tannersville
$238 nightly
The price is $253
Jul 28 - Jul 29
Total with taxes and fees
Jessie's Harvest House
Exterior

2 Bedrooms 1 Mile to Ski Slope and Festivals - Privately Secluded Yet Convenient

2 Bedrooms 1 Mile to Ski Slope and Festivals - Privately Secluded Yet Convenient
Hunter
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Trish's chalet! The home is beautifully decorated with a zen, artistic style that feels both cozy and thoughtfully curated. Every room was comfortable and well-appointed, making it easy to relax and settle in from the moment we arrived.The beds were especially comfortable, which made for a great night of sleep. The outdoor spaces were really lovely. There were plenty of places out back to gather, relax, and enjoy the beauty of the surrounding woods. The fact that...
United States
Deborah K.
$620 nightly
The price is $670
Jul 24 - Jul 25
Total with taxes and fees
2 Bedrooms 1 Mile to Ski Slope and Festivals - Privately Secluded Yet Convenient
Property grounds

Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
$648 nightly
The price is $700
Jul 28 - Jul 29
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Exterior

Modern Mountain View Chalet in Windham

Modern Mountain View Chalet in Windham
Windham
10.0 out of 10, Exceptional, (7 reviews)
"Highly recommend staying here. The house is beautiful, spacious yet cozy, very clean, and well stocked with everything you need. We really enjoyed our stay and would stay again! "
United States
Charles C.
$897 nightly
The price is $969
Jul 27 - Jul 28
Total with taxes and fees
Modern Mountain View Chalet in Windham
Outdoor dining

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
10.0 out of 10, Exceptional, (8 reviews)
"We had an amazing get away! Yasmin is a great host very informative. The house is well stocked and the views were amazing. Quick trip to town and the mountain."
United States
Babette n.
$1,667 nightly
The price is $1,800
Jul 26 - Jul 27
Total with taxes and fees
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Property grounds

Luxe Party Retreat: Ski Pool Karaoke Game Movie

Luxe Party Retreat: Ski Pool Karaoke Game Movie
Jewett
10.0 out of 10, Exceptional, (2 reviews)
"Super fun home with a lot of bells and whistles!"
United States
Bennett Z.
$2,292 nightly
The price is $2,475
Jul 31 - Aug 1
Total with taxes and fees
Luxe Party Retreat: Ski Pool Karaoke Game Movie
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 Round Top Hotel Reviews

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

8/10 Good
"$75 pet fee too expensive however everything else was just fine"
Sal 1-night trip
Posted less than an hour ago
Spark by Hilton West Coxsackie

Find out more about Round Top

Round Top Chalets information

Number of reviews
61
Accommodation
51 Chalets
Lowest Price
$190
Highest Price
$2,475

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