Chalet holiday rentals in Massachusetts
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Top-rated chalet rentals in Massachusetts
Guests agree: These chalets are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Massachusetts chalet rentals
Family-friendly chalet rentals
Chalet in Lee
4.81 out of 5 average rating, 59 reviewsWaterfront lakehouse in Berkshires
8–15 May
Chalet in Stockbridge
4.6 out of 5 average rating, 5 reviewsThe Millhouse
9–16 Jan
Chalet in West Tisbury
4.63 out of 5 average rating, 16 reviewsStay Cool in West Tisbury (Lambert's Cove Beach!)
31 Aug – 7 Sep
Chalet in Otis
4.94 out of 5 average rating, 350 reviewsMid-Century Glass Octagon in the Berkshires
10–17 Dec
Chalet in Monterey
4.97 out of 5 average rating, 73 reviewsCozy French Country chalet
23–30 Jan
Chalet in New Marlborough
4.92 out of 5 average rating, 50 reviewsModern & Secluded on 40 Acres - Fast Wi-fi
5–12 Dec
Chalet in Peru
4.92 out of 5 average rating, 252 reviewsSwiss Chalet Style Timberframe Home in Berkshires
9–16 Jan
Chalet in West Stockbridge
4.8 out of 5 average rating, 15 reviewsTranquility Glade - Tanglewood in minutes
8–15 Aug
Luxury chalet rentals
Chalet in Monterey
5.0 out of 5 average rating, 10 reviewsStunning Log Cabin
13–20 Jun
Room in Taunton
The Bay Chalet with Game Room and Bar
11–18 May
Chalet in New Marlborough
4.92 out of 5 average rating, 50 reviewsModern & Secluded on 40 Acres - Fast Wi-fi
5–12 Dec
Chalet in Otis
4.89 out of 5 average rating, 35 reviewsLake, Kayaks & Sauna - Family & Wellness
24–31 Dec
Chalet in West Stockbridge
4.8 out of 5 average rating, 15 reviewsTranquility Glade - Tanglewood in minutes
8–15 Aug
Destinations to explore
- Chalet rentals United States
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