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Featured Villas in Pittsfield and around

Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.
Pool

Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.

10.0 out of 10, Exceptional, (2)
"great room. clean. there is everything you need for a comfortable stay. definitely 5 stars. We'll be back."
Pinnacle D02, Lovely 2 bedroom, 2 bath unit with shuttle to the slopes everyday of the week. The outdoor pool, hot tub and tennis courts are open during summer only.
Hakuna Matata - GetAway
Townhome, 3 Bedrooms, Mountain View, Mountainside | Private kitchen

Hakuna Matata - GetAway

3.5 star property
6.0 out of 10, (1)
Hakuna Matata - GetAway
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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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Frequently asked questions

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