A mountainous landscape with dense forests and a rocky cliff.

Search Chalets in Round Top from CA $239

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Round Top chalets

A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

1. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is CA $163
CA $276 total
includes taxes & fees
Sep 10 - Sep 11
Jessie's Harvest House
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

2. 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.
The price is CA $130
CA $239 total
includes taxes & fees
Sep 14 - Sep 15
Jessie's Harvest House Suite
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

3. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is CA $163
CA $276 total
includes taxes & fees
Sep 10 - Sep 11
Jessie's Harvest House
A log cabin with a porch, a staircase, and a garage.

4. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (31 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is CA $179
CA $302 total
includes taxes & fees
Sep 10 - Sep 11
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

5. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is CA $163
CA $276 total
includes taxes & fees
Oct 5 - Oct 6
Jessie's Harvest House
A picnic setup with a wine glass, bottle, cheese, tomatoes, and grapes on a wooden table with a view of a grassy field and hills.

6. 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.
The price is CA $328
CA $1,111 total
includes taxes & fees
Sep 10 - Sep 11
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A snowy landscape with a wooden deck and a house in the background.

7. 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.
The price is CA $542
CA $925 total
includes taxes & fees
Sep 14 - Sep 15
Beautiful Windham Chalet 2 minutes to Town and the Mountain
An outdoor dining area with a grill, wooden table, wicker chairs, and a stone wall backdrop.

8. 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, (9 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is CA $1,213
CA $2,432 total
includes taxes & fees
Sep 10 - Sep 11
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"This was an extremely delightful stay for end of summer! Great setting with beautiful grounds, easy to get anywhere in Hunter and all the other nearby towns. Stayed in a King loft which was great, lots of room to relax, very clean and well maintained. It was very handy to have a mini-fridge and microwave, but also enjoyed dinner downstairs at the Tavern. The complementary breakfast hit just right before hitting the road for the day."
Theresa 3-night trip
Posted 21 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Round Top

Round Top Chalets information

Number of reviews
59
Accommodation
42 Chalets
Lowest Price
CA $239
Highest Price
CA $2,432

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