Cottage holiday rentals in Pioneer Valley
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Top-rated cottage rentals in Pioneer Valley
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pioneer Valley cottage rentals
Cottage rentals with a hot tub
Cottage in Pownal
5 out of 5 average rating, 29 reviewsBeautiful, 100 Acre Retreat, Williamstown 10 Mins
Cottage in Lanesborough
5 out of 5 average rating, 14 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
Cottage in Southwick
4.98 out of 5 average rating, 92 reviewsPrivate Hot Tub with Lake Views Fire Pit & Kayaks
Cottage in Monterey
4.71 out of 5 average rating, 14 reviewsmountain refuge
Cottage in Norfolk
4.92 out of 5 average rating, 12 reviewsThe Cottage at Blackberry River Inn
Cottage in Williamsburg
4.71 out of 5 average rating, 117 reviewsNorthampton-area Hot tub Pet Friendly
Cottage in Becket
4.65 out of 5 average rating, 165 reviewsA Magical Spot on Little Robin Lake
Cottage in Otis
4.98 out of 5 average rating, 43 reviewsBerkshire lakefront cabin with modern luxuries
Pet-friendly cottage rentals
Cottage in Williamstown
4.89 out of 5 average rating, 179 reviewsCute Cozy Comfy Cottage in the Berkshires
Cottage in Great Barrington
4.92 out of 5 average rating, 66 reviewsCarriage house with Chef's Kitchen, close to town
Cottage in Warwick
4.94 out of 5 average rating, 31 reviewsBy Still Waters Cottage
Cottage in Becket
4.77 out of 5 average rating, 156 reviewsTranquil Lake Cottage on 3 Acres with Large Deck
Cottage in Williamsburg
4.77 out of 5 average rating, 71 reviewsA Place for Peace - perfectly imperfect!
Cottage in Windsor
4.9 out of 5 average rating, 172 reviewsIn-law apartment in Farmington River Cottage
Cottage in Brimfield
4.98 out of 5 average rating, 61 reviewsCheerful 2 bedroom cottage with lake access.
Cottage in Winchester
4.92 out of 5 average rating, 48 reviewsStorybook Lake Front Villa with Private Beach!
Private cottage rentals
Cottage in Lee
4.99 out of 5 average rating, 100 reviewsCharming Renovated Berkshire Home
Cottage in Guilford
4.96 out of 5 average rating, 118 reviewsGreen River Cottage
Cottage in Lanesborough
4.93 out of 5 average rating, 237 reviewsStone School Cottage
Cottage in Hinsdale
4.99 out of 5 average rating, 152 reviewsCozy Cottage in the Berkshires
Cottage in Vernon
4.97 out of 5 average rating, 108 reviewsVintage Bolton Lake
Cottage in Williamstown
4.99 out of 5 average rating, 105 reviewsCharming Williamstown Cottage
Cottage in Amherst
4.99 out of 5 average rating, 76 reviewsSerene Modern Country Cottage near Amherst Center
Cottage in Sturbridge
4.96 out of 5 average rating, 140 reviewsCedar Sunrise
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- Cottage rentals The Hamptons
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