House holiday rentals in Pioneer Valley
Find and book unique houses on Airbnb
Top-rated house rentals in Pioneer Valley
Guests agree: these houses 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 house rentals in Pioneer Valley
House rentals with a pool
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
14–21 Oct
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
18–25 Feb
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
1–8 Feb
Home in Chesterfield
4.98 out of 5 average rating, 44 reviewsHigh Field Farm
8–15 Dec
Home in Shelburne Falls
4.95 out of 5 average rating, 19 reviewsBeautiful home for a cozy family getaway! W/pool !
12–19 Jun
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
25 Jan – 1 Feb
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
28 Sep – 5 Oct
Home in Lenox
4.96 out of 5 average rating, 24 reviewsLenox Grand Colonial with Pool by Evergreen Home
18–25 Oct
Weekly house rentals
Home in Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
23–30 Nov
Home in Lee
4.89 out of 5 average rating, 236 reviewsCozy Berkshires Cottage
8–15 Oct
Home in Manchester
4.94 out of 5 average rating, 176 reviewsParadise On The Hill Luxury Apartment.
5–12 Nov
Home in Russell
4.96 out of 5 average rating, 227 reviewsSouth Quarter House
21–28 Dec
Home in Great Barrington
4.96 out of 5 average rating, 214 reviewsJaw dropping mountain & lake views
5–12 Apr
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
23–30 Nov
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
10–17 Mar
Home in Becket
4.86 out of 5 average rating, 290 reviewsReal Estate:Therapy - Lake, Laundry, Love it
24 Feb – 3 Mar
Private house rentals
Home in Northampton
4.95 out of 5 average rating, 59 reviewsFlorence Cottage
21–28 Nov
Home in Deerfield
4.97 out of 5 average rating, 33 reviewsLUXE Brand New Home w/ Historic Charm, SO COZY!
19–26 Sep
Home in Springfield
5.0 out of 5 average rating, 10 reviewsQuiet 2 Bedroom - near Big E, Massmutual, Six Flag
25 Dec – 1 Jan
Home in Williamsburg
5.0 out of 5 average rating, 70 reviewsThe Gate House, EV Charger, Farm View
21–28 Aug
Home in Northampton
4.98 out of 5 average rating, 99 reviewsDiscover Cozy Elegance in the Heart of Northampton
29 Mar – 5 Apr
Home in Belchertown
5.0 out of 5 average rating, 19 reviewsMoonstone n' Lucy's Lake House – romantic, serene
16–23 Oct
Home in Becket
4.95 out of 5 average rating, 38 reviewsNerd Preservation Sanctuary
14–21 Dec
Home in Pelham
4.95 out of 5 average rating, 20 reviewsAmherst/Pelham getaway with a view!
7–14 Nov
Destinations to explore
- Guest house rentals United States
- House rentals United States
- Earth house rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals Boston
- Beach house rentals Boston
- Townhouse rentals Boston
- Guest house rentals Boston
- Guest house rentals The Hamptons
- Beach house rentals The Hamptons
- House rentals The Hamptons
- Tiny house rentals New Hampshire
- Beach house rentals New Hampshire
- House rentals New Hampshire
- Lakehouse rentals New Hampshire
- Townhouse rentals New Hampshire
- Guest house rentals New Hampshire
- Townhouse rentals Massachusetts
- Lakehouse rentals Massachusetts
- Tiny house rentals Massachusetts
- House rentals Massachusetts
- Beach house rentals Massachusetts
- Guest house rentals Massachusetts
- Apartment rentals Pioneer Valley
- Fitness-friendly rentals Pioneer Valley
- Rentals with a firepit Pioneer Valley
- Rentals with a patio Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with beach access Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Rentals with pools Pioneer Valley
- Private suite rentals Pioneer Valley
- Waterfront rentals Pioneer Valley
- Flat rentals Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
- Rentals with an EV charger Pioneer Valley
- Monthly Rentals Pioneer Valley
- Rentals with outdoor seating Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Rentals with a washing machine and dryer Pioneer Valley
- Rentals with a fireplace Pioneer Valley
- Pet-friendly rentals Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Cottage rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Cabin rentals Pioneer Valley
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom