Chalets in Sullivan County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Sullivan County chalets

Terrace/patio

Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front
Jamaica
9.4 out of 10, Exceptional, (81 reviews)
"This place was just what we need to get away from big-city living for a week."
United States
Scott P.
Two Bedroom Chalet, Charming, Quiet, River Front
Exterior

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Ludlow
9.6 out of 10, Exceptional, (38 reviews)
"Great stay"
United States
ali m.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Exterior

Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.

Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
Windham
9.8 out of 10, Exceptional, (8 reviews)
Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
Exterior

Peaceful Nest / Nirvana Amidst Trees

Peaceful Nest / Nirvana Amidst Trees
Hill
9.8 out of 10, Exceptional, (119 reviews)
"The host was very welcoming and accommodating with last-minute changes.The place was absolutely beautiful. The views were amazing peace and quiet just what we needed. All I can say is amazing. Amazing amazing would love to go back and stay again."
United States
Michele M.
Peaceful Nest / Nirvana Amidst Trees
Property grounds

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Ludlow
10.0 out of 10, Exceptional, (47 reviews)
"Excellent home & host. Thanks !"
United States
Sam F.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Property grounds

Best value on Newfound Lake NH 2 day min

Best value on Newfound Lake NH 2 day min
Bristol
8.8 out of 10, Excellent, (26 reviews)
"Perfect stay! Exactly as described, great little cabin and was perfect for a family weekend "
United States
Kasey C.
Best value on Newfound Lake NH 2 day min
Exterior detail

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Plymouth
9.8 out of 10, Exceptional, (30 reviews)
"Great pet friendly property perfectly located between Woodstock and Killington. "
United States
Norman Y.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

Stratton Mountain Escape w Hot Tub|Deck|Projector

Stratton Mountain Escape w Hot Tub|Deck|Projector
East Jamaica
10.0 out of 10, Exceptional, (6 reviews)
"This is a beautiful place. Has everything you need for an enjoyable stay. Watching the firefly show at night from the deck was amazing. "
United States
Christopher V.
Stratton Mountain Escape w Hot Tub|Deck|Projector
Exterior

Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
ludlow
10.0 out of 10, Exceptional, (30 reviews)
"Our stay was great! House was excellent, location was perfect, and Dave was super accommodating!"
United States
Anna B.
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
Exterior

3-bedroom chalet next to skiing, hiking, boating and breweries

3-bedroom chalet next to skiing, hiking, boating and breweries
Bradford
10.0 out of 10, Exceptional, (11 reviews)
"The house was great. Plenty of room to spread out and great views from the living room and deck. The fire pit was an added bonus and all the necessary wood, kindling & lighters were all provided. Well appointed kitchen and the house was clean. Would definitely stay again!"
United States
Ben G.
3-bedroom chalet next to skiing, hiking, boating and breweries
Property grounds

Mountain chalet

Mountain chalet
Londonderry
10.0 out of 10, Exceptional, (45 reviews)
"Amazing house and location. Thank you!"
United States
John A.
Mountain chalet
Terrace/patio

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great space for large family gathering! "
United States
ted d.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Terrace/patio

Amazingly Beautiful Waterfalls Getaway

Amazingly Beautiful Waterfalls Getaway
Hill
10.0 out of 10, Exceptional, (98 reviews)
"Great experience, the owners are really friendly, great views we definitely thinking about coming back eventually."
United States
Ian v.
Amazingly Beautiful Waterfalls Getaway
Exterior

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Ludlow
9.8 out of 10, Exceptional, (133 reviews)
"It was exactly as described. The host was very helpful and responsive. It was perfect for our family getaway!!!! "
United States
Jeannine F.
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (15 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior

Cozy 2-bedroom A Frame chalet in delightful Danbury NH with WiFi and AC

Cozy 2-bedroom A Frame chalet in delightful Danbury NH with WiFi and AC
Danbury
10.0 out of 10, Exceptional, (13 reviews)
"This place is so beautiful."
United States
Andena T.
Cozy 2-bedroom A Frame chalet in delightful Danbury NH with WiFi and AC
Property grounds

Direct Waterfront, Year-Round, A-Frame Cabin

Direct Waterfront, Year-Round, A-Frame Cabin
Antrim
10.0 out of 10, Exceptional, (10 reviews)
"Perfect place for a quick getaway! Lovely house in a great location!"
United States
Johnna P.
Direct Waterfront, Year-Round, A-Frame Cabin
Outdoor spa tub

Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village

Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
Ludlow
9.4 out of 10, Exceptional, (27 reviews)
"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "
United States
Tom G.
Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
Exterior

Silver Birch Chalet: Mountain Apt w/ Hot Tub

Silver Birch Chalet: Mountain Apt w/ Hot Tub
Londonderry
Silver Birch Chalet: Mountain Apt w/ Hot Tub
Terrace/patio

Okemo Mountain Chalet W/ Hot Tub and Game Room

Okemo Mountain Chalet W/ Hot Tub and Game Room
Ludlow
9.8 out of 10, Exceptional, (164 reviews)
"Perfect for our multi-generational family get together!"
United States
Michael B.
Okemo Mountain Chalet W/ Hot Tub and Game Room
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sullivan County Hotel Reviews

Six South St Hotel

Six South St Hotel

8/10 Good
"Room was clean but allergies acted up once inside room. Nice touch of supplying bottles of water and ice packages in each lobby. "
Christian or Andrea 1-night trip
Posted 2 hours ago
Six South St Hotel