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 Great Barrington
4.93 out of 5 average rating, 237 reviewsArtist Cottage
23–30 Jan
Cottage in Litchfield
4.89 out of 5 average rating, 259 reviewsLitchfield - Hot Tub - Mohawk Mountain - Fireplace
18–25 Dec
Cottage in Southwick
4.97 out of 5 average rating, 64 reviews4 Kayaks Lake View from Hot Tub Fire Pit Six Flags
30 Sep – 7 Oct
Cottage in Williamsburg
4.71 out of 5 average rating, 99 reviewsNorthampton-area Hot tub Pet Friendly
11–18 Sep
Cottage in Burlington
5.0 out of 5 average rating, 43 reviewsCozy Cottage w/Lakefront Views, Swim Spa & Firepit
27 Nov – 4 Dec
Cottage in Eastford
4.89 out of 5 average rating, 75 reviewsSerenity Ashford Lake
17–24 Jul
Cottage in Lanesborough
5.0 out of 5 average rating, 11 reviewsNorte Maison 2 beds 2 Baths Minutes to Jiminy Peak
9–16 May
Cottage in Rindge
4.79 out of 5 average rating, 53 reviewsWaterfront Cottage with a HOT TUB
8–15 Apr
Pet-friendly cottage rentals
Cottage in Windsor
4.89 out of 5 average rating, 164 reviewsIn-law apartment in Farmington River Cottage
3–10 Jun
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
12–19 Feb
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
12–19 Apr
Cottage in Sheffield, The Berkshires
4.93 out of 5 average rating, 105 reviewsCheerful 3-bedroom cottage with woodstove.
10–17 Apr
Cottage in North Bennington
4.9 out of 5 average rating, 292 reviewsRomantic Private Vermont Cottage - Waterfront
Cottage in Cornwall
4.94 out of 5 average rating, 116 reviewsNewly Built Cottage in Housatonic Valley
24 Sep – 1 Oct
Cottage in Canaan
4.9 out of 5 average rating, 126 reviewsPlan your Berkshires by the lake
24 Sep – 1 Oct
Cottage in Monroe
4.89 out of 5 average rating, 83 reviewsPumpkin Pine Cottage: your next adventure awaits!
13–20 Mar
Private cottage rentals
Cottage in Goshen
4.98 out of 5 average rating, 103 reviewsCountry Cottage in Goshen
28 Jan – 4 Feb
Cottage in Chaplin
4.88 out of 5 average rating, 129 reviewsClark Cottage in the historic village in Chaplin
30 Nov – 7 Dec
Cottage in New Lebanon
4.94 out of 5 average rating, 176 reviewsThe Writer's Cottage
8–15 Feb
Cottage in West Stockbridge
4.98 out of 5 average rating, 107 reviewsHistoric 1810 Farmhouse - Fully Renovated
30 May – 6 Jun
Cottage in Hinsdale
4.99 out of 5 average rating, 141 reviewsCozy Cottage in the Berkshires
1–8 Apr
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone School Cottage
21–28 Sep
Cottage in Collinsville
4.96 out of 5 average rating, 112 reviewsThe Carriage House
11–18 Mar
Cottage in Dover
4.84 out of 5 average rating, 263 reviewsCozy Camp in Vermont
7–14 May
Destinations to explore
- Cottage rentals Boston
- Cottage rentals The Hamptons
- Cottage rentals New Hampshire
- Cottage rentals Massachusetts
- Rentals with lake access Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
- Rentals with beach access Pioneer Valley
- House rentals Pioneer Valley
- Cabin rentals Pioneer Valley
- Private suite rentals Pioneer Valley
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- Pet-friendly rentals Pioneer Valley
- Rentals with outdoor seating Pioneer Valley
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- Monthly Rentals Pioneer Valley
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- Rentals with a kayak Pioneer Valley
- Condo rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Rentals with a fire pit Pioneer Valley
- Rentals with pools Pioneer Valley
- Rentals with a washing machine and dryer Pioneer Valley
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