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, 31 reviewsBeautiful, 100 Acre Retreat, Williamstown 10 Mins
Cottage in Lanesborough
5 out of 5 average rating, 15 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
Cottage in Southwick
4.98 out of 5 average rating, 96 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, 118 reviewsNorthampton-area Hot tub Pet Friendly
Cottage in Great Barrington
4.85 out of 5 average rating, 33 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Cottage in Becket
4.65 out of 5 average rating, 165 reviewsA Magical Spot on Little Robin Lake
Pet-friendly cottage rentals
Cottage in Orange
4.89 out of 5 average rating, 105 reviewsThe Film Shack: A Sweetwater Stay
Cottage in Woodford
4.95 out of 5 average rating, 42 reviewsHoneyBear Lake Cottage
Cottage in Orange
4.93 out of 5 average rating, 165 reviewsThe Lake Cottage: A Sweetwater Stay
Cottage in Windsor
4.89 out of 5 average rating, 174 reviewsIn-law apartment in Farmington River Cottage
Cottage in Brimfield
4.98 out of 5 average rating, 65 reviewsCheerful 2 bedroom cottage with lake access.
Cottage in Monterey
4.94 out of 5 average rating, 18 reviewsNew! Fully renovated private cottage
Cottage in Granby
4.89 out of 5 average rating, 177 reviewsThe Little Red Schoolhouse ~ Circa 1877
Cottage in New Lebanon
4.89 out of 5 average rating, 46 reviewsCozy Cottage in the Clouds With Mountain Views
Private cottage rentals
Cottage in Becket
4.88 out of 5 average rating, 91 reviewsStylish Shales Brook Cottage-Cozy up to happiness
Cottage in Hancock
4.86 out of 5 average rating, 78 reviewsBerkshire Cottage Queen Bd-Jiminy Peak 3 mi
Cottage in Becket
4.81 out of 5 average rating, 52 reviewsCozy Cottage on the Lake
Cottage in Hinsdale
4.98 out of 5 average rating, 81 reviewsBerkshires - Charming Lakefront Cottage
Cottage in Amherst
4.99 out of 5 average rating, 79 reviewsSerene Modern Country Cottage near Amherst Center
Cottage in Harwinton
4.97 out of 5 average rating, 34 reviewsNewly renovated 2 bedroom cottage on the lake!
Cottage in Wilmington
5 out of 5 average rating, 30 reviewsEmerald Cottage Mt. Snow
Cottage in Jaffrey
4.97 out of 5 average rating, 30 reviewsThe Boathouse - A rustic and cozy lakeside cottage
Destinations to explore
- Cottage rentals The Hamptons
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