Town of Southeast ski-in/ski-out rentals

We found 2 ski-in/ski-out rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Town of Southeast

Showing deals for: 1 Feb - 4 Feb

Charming Grand View/Lake Loft in Brewster with WiFi, AC

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 room

AU$329 per night

includes taxes & fees

Premier Host

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Sleeps 16 · 11 bedrooms · 5 bathrooms

for 3 nights, 1 villa

AU$1,838 per night

includes taxes & fees

Top rated rentals - Town of Southeast

Premier Host

Lovely and homey

Kim and Kevin were super communicative and friendly, and the home was clean and beautifully decorated. The coffee cake was the cherry on top. Perfect for our group! Would absolutely stay again.

Emily H.

Stayed May 2025

Spiral staircase leading to the mezzanine where the bedroom is located.

Cute!

Sitting outside the cottage overlooking the reservoir (on other side of road) was superb after being in hectic New York. The bed was comfy but located up a steep, narrow spiral staircase. Small bathroom downstairs. Eclectic furnishings. Very clean. Would recommend seniors opt for house option rather than cottage. Host very pleasant.

Deborah W.

Stayed Sept 2024