Cottage vacation 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.
Vacation 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 Lanesborough
5.0 out of 5 average rating, 11 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
May 10 – 17
Cottage in Rindge
4.79 out of 5 average rating, 53 reviewsWaterfront Cottage with a HOT TUB
Apr. 10 – 17
Cottage in Eastford
4.89 out of 5 average rating, 75 reviewsSerenity Ashford Lake
Jun. 20 – 27
Cottage in Williamsburg
4.71 out of 5 average rating, 99 reviewsNorthampton-area Hot tub Pet Friendly
Jul. 1 – 8
Cottage in Southwick
4.97 out of 5 average rating, 65 reviews4 Kayaks Lake View from Hot Tub Fire Pit Six Flags
Dec. 10 – 17
Cottage in Monterey
4.88 out of 5 average rating, 8 reviewsmountain refuge
Sep. 16 – 23
Cottage in Coventry
4.82 out of 5 average rating, 17 reviewsLakefront Connecticut Retreat Near UConn
Jun. 29 – Jul. 6
Cottage in Otis
4.96 out of 5 average rating, 28 reviewsBerkshire lakefront cabin with modern luxuries
Jun. 12 – 19
Pet-friendly cottage rentals
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
Apr. 25 – May 2
Cottage in Monroe
4.89 out of 5 average rating, 84 reviewsPumpkin Pine Cottage: your next adventure awaits!
Mar. 2 – 9
Cottage in Warwick
5.0 out of 5 average rating, 19 reviewsBy Still Waters Cottage
Apr. 22 – 29
Cottage in Winchester
4.93 out of 5 average rating, 27 reviewsStorybook Lake Front Villa with Private Beach!
Aug. 30 – Sep. 6
Cottage in Guilford
4.97 out of 5 average rating, 67 reviewsThe Blacksmith Shop
Jun. 25 – Jul. 2
Cottage in Brimfield
5.0 out of 5 average rating, 31 reviewsCheerful 2 bedroom cottage with lake access.
Jul. 22 – 29
Cottage in Becket
4.76 out of 5 average rating, 139 reviewsPrivate Lake Cottage on 3 acres w/350 sq. ft. deck
Sep. 28 – Oct. 5
Cottage in Pittsfield
4.9 out of 5 average rating, 69 reviewsCottage Getaway - access all the Berkshires offer!
Sep. 5 – 12
Private cottage rentals
Cottage in Chaplin
4.88 out of 5 average rating, 130 reviewsClark Cottage in the historic village in Chaplin
Mar. 19 – 26
Cottage in Hinsdale
4.99 out of 5 average rating, 141 reviewsCozy Cottage in the Berkshires
Dec. 30 – Jan. 6
Cottage in Guilford
4.97 out of 5 average rating, 105 reviewsGreen River Cottage Retreat
Oct. 24 – 31
Cottage in Sturbridge
4.96 out of 5 average rating, 123 reviewsCedar Sunrise
Oct. 6 – 13
Cottage in Enfield
4.87 out of 5 average rating, 145 reviewsHilda’s Riverside Retreat
Feb. 18 – 25
Cottage in New Marlborough
4.96 out of 5 average rating, 104 reviewsConverted Berkshire schoolhouse on a quiet river
Dec. 15 – 22
Cottage in Deerfield
4.97 out of 5 average rating, 90 reviewsDreamy Guesthouse: sauna and private deck
Jan. 3 – 10
Cottage in Wendell
4.98 out of 5 average rating, 60 reviewsCozy Scenic Cottage on Small Pond, Near Lake Wyola
Sep. 7 – 14
Destinations to explore
- Cambridge Vacation rentals
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- Rentals with a kayak Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Waterfront rentals Pioneer Valley
- Rentals with a firepit Pioneer Valley
- Kid-friendly rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Rentals with outdoor seating Pioneer Valley
- Bed and breakfasts Pioneer Valley
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- House rentals Pioneer Valley
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- Apartment rentals Pioneer Valley
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- Rentals with a fireplace Pioneer Valley
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- Rentals with an EV charger Pioneer Valley
- Private suite rentals Pioneer Valley
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- Rentals with lake access Pioneer Valley
- Rentals with a washer and dryer Pioneer Valley
- Pet-friendly rentals Pioneer Valley
- Monthly Rentals Pioneer Valley
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