Pittsfield Chalets
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Compare 30 Chalets in Pittsfield with updated reviews, rates, and availability.
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
9.0 out of 10, Wonderful, (6)
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
9.8 out of 10, Exceptional, (37)
Save an average of 15% on thousands of hotels when you're signed in
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
9.8 out of 10, Exceptional, (13)
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
South View Chalet!
South View Chalet!
9.2 out of 10, Wonderful, (25)
Tree Top Home with Hot Tub Near Killington & Okemo
Tree Top Home with Hot Tub Near Killington & Okemo
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
9.8 out of 10, Exceptional, (19)
BearHaus- Central AC, HUGE Hot Tub, FirePit
BearHaus- Central AC, HUGE Hot Tub, FirePit
10.0 out of 10, Exceptional, (1)
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
10.0 out of 10, Exceptional, (2)
Dreamy Artist Chalet in Secluded Historic Village
Dreamy Artist Chalet in Secluded Historic Village
8.0 out of 10, Very Good, (4)
The price is $300
$465 total
includes taxes & fees
Jun 2 - Jun 3
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort, Dog Friendly
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort, Dog Friendly
9.4 out of 10, Exceptional, (10)
BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf
BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf
10.0 out of 10, Exceptional, (9)
Secluded 2600 sqft home 15 min from Okemo and Killington
Secluded 2600 sqft home 15 min from Okemo and Killington
10.0 out of 10, Exceptional, (3)
Gnome Home Mountain Ski Chalet w/Sauna Killington
Gnome Home Mountain Ski Chalet w/Sauna Killington
10.0 out of 10, Exceptional, (2)
The price is $179
$447 total
includes taxes & fees
May 30 - May 31
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
10.0 out of 10, Exceptional, (3)
New Construction Timber Frame / Mins to mountain and restaurants / Amazing views
New Construction Timber Frame / Mins to mountain and restaurants / Amazing views
10.0 out of 10, Exceptional, (2)
Romantic Cozy Mountain Retreat near Killington
Romantic Cozy Mountain Retreat near Killington
10.0 out of 10, Exceptional, (6)
The Overlook - Hot Tub, Game Room, 5min to MTN
The Overlook - Hot Tub, Game Room, 5min to MTN
10.0 out of 10, Exceptional, (1)
Country house minutes from Killington and Okemo
Country house minutes from Killington and Okemo
10.0 out of 10, Exceptional, (5)
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.
Other property types in Pittsfield
Killington area home - 4-seasons & hot tub. Sleeps 12+
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
Cozy Loft for two with Hot Tub
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
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.
Pittsfield Chalets information
Number of reviews | 263 |
---|---|
Accommodation | 30 Chalets |
Lowest Price | $179 |
Highest Price | $300 |
Recent reviews of Pittsfield hotelsExpedia verified reviews
5/5 Excellent
"Late season stay, great price and service. "
A verified traveler stayed at North Star Lodge and Resort
Posted 14 hours ago
Popular Destinations
More Accommodation Types in Pittsfield
- Vacation Homes in Pittsfield (471)
- Condo Rentals in Pittsfield (453)
- Apartments in Pittsfield (81)
- Cabin Rentals in Pittsfield (54)
- Cottages in Pittsfield (33)
- Lodges in Pittsfield (31)
- B&B in Pittsfield (17)
- Aparthotels in Pittsfield (13)
- Motels in Pittsfield (9)
- Farmstay in Pittsfield (8)
- Guest Houses in Pittsfield (5)
- Resorts in Pittsfield (4)
- Villas in Pittsfield (2)
- Hotels (1,605)
All Accommodation Types
Be inspired: Top Chalets destinations in 2024
- Gatlinburg Chalets
- Pigeon Forge Chalets
- Switzerland Chalets
- Mont-Tremblant Chalets
- Val-d'Isere Chalets
- Chamonix-Mont-Blanc Chalets
- France Chalets
- Zermatt Chalets
- Pine Mountain Chalets
- Quebec Chalets
- Austria Chalets
- Killington Chalets
- Lake Arrowhead Chalets
- Whistler Chalets
- Banff Chalets
- Megeve Chalets
- Morzine Chalets
- Colorado Chalets
- Singapore Chalets
- Cooperstown Chalets
Most searched themes and destinations in 2024
- Ski Resorts in Taos Ski Valley
- Ski Resorts in Park City
- Ski Resorts in Whistler
- Ski Resorts in Denver
- Ski Resorts in Big Bear Lake
- Ski Resorts in Vail
- Ski Resorts in Steamboat Springs
- Ski Resorts in Breckenridge
- Ski Resorts in New York
- Ski Resorts in Copper Mountain
- Ski Resorts in Mammoth Lakes
- Ski Resorts in Aspen
- Ski Resorts in Stowe
- Ski Resorts in Banff
- Ski Resorts in Killington
- Ski Resorts in Mont Tremblant
- Ski Resorts in Beech Mountain
- Ski Resorts in Salt Lake City
- Ski Resorts in Key West
- Ski Resorts in Crested Butte
Expedia's Latest Trends
Hotels
Hotels in BarreHotels in StoweHotels in RutlandHotels in BenningtonHotels in BrattleboroHotels in WaterburyHotels in StrattonHotels in St. JohnsburyStowe Cheap HotelsHotels in South BurlingtonBurlington Cheap HotelsHotels in Essex JunctionHotels in White River JunctionHotels in St. AlbansHotels in MontpelierHotels in ColchesterHotels in WoodstockHotels in WillistonHotels in KillingtonHotels in BurlingtonHotels in MiddleburyBurlington Hotels with Free Airport ShuttleHotels in LudlowBurlington Pet-friendly Hotels
Packages
General