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House holiday rentals in Pittsfield

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Top-rated house rentals in Pittsfield

Guests agree: These houses are highly rated for location, cleanliness and more.

Guest favourite
Home in Canaan
Country Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
23 – 30 Jan
Guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!
10 – 17 Feb
Guest favourite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
Enjoy a retreat in a home full of history - it was a tavern/stage coach stop in the 1800's. Today we have added modern comfort while keeping the charm. We are centrally located in the Berkshires making it easy to enjoy -ski Jiminy, hike Mt. Greylock, and enjoy the culture. Or stay in and unwind. Play games on the flat 3-acre yard or try yoga surrounded by nature. Work remotely in our library. Walk down our country road and enjoy the farms. Most of all, reconnect with family/friends.
11 – 18 Sept

Popular amenities for Pittsfield house rentals

House rentals with a pool

Guest favourite
Home in Ghent
Modern Barn on 12 acres w Sauna, FirePit+swimming
18 – 25 Sept
Guest favourite
Home in Saugerties
Wilderkill Catskill Retreat, Mountain Modern Barn
29 Apr – 6 May
Guest favourite
Home in Hudson
Casa Luna Country Retreat with Pool, Hudson, NY
14 – 21 Oct
Guest favourite
Home in Woodstock
Woodstock Mediterranean Retreat: Heated Pool
23 – 30 Apr
Guest favourite
Home in Cottekill
Peace & Privacy - High Falls (hot tub & salt pool)
5 – 12 Mar
Guest favourite
Home in Rhinebeck
On The Hill in Rhinebeck
24 – 31 Mar
Guest favourite
Home in Colrain
The 1770 House
30 Nov – 7 Dec
Superhost
Home in Deerfield
Perfectly Polished Deerfield Home 5 min to I-91
25 Apr – 2 May
Guest favourite
Home in Wilmington
4 bedroom Ski House 15 min to Mount Snow
31 Oct – 7 Nov
Guest favourite
Home in Catskill
The Grandview | Catskill, NY
20 – 27 Mar
Guest favourite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
4 – 11 Sept
Guest favourite
Home in Pittsfield
Stunning Berkshires Retreat, Large and Private
7 – 14 Dec

Weekly house rentals

Guest favourite
Home in New Lebanon
The old sawmill from 1771
20 – 27 Aug
Guest favourite
Home in Lee
Cozy Berkshires Cottage
22 – 29 May
Guest favourite
Home in Pownal
Cozy Vermont mini-house
7 – 14 May
Guest favourite
Home in Chester
Riverfront Getaway
23 – 30 Aug
Guest favourite
Home in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
5 – 12 Nov
Guest favourite
Home in Lee
1817 Berkshire Farmhouse- Close to Everything.
23 – 30 June
Guest favourite
Home in Pittsfield
Dancing Horse Lodge
10 – 17 Feb
Guest favourite
Home in Bennington
Cozy Modern Sugar House with spectacular views.
28 Dec – 4 Jan
Guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
17 – 24 Sept
Guest favourite
Home in Lenox
The Berkshire Quintessential Cape downtown Lenox
4 – 11 Feb
Guest favourite
Home in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
16 – 23 Aug
Superhost
Home in Lenox
Berkshire, MA Getaway! Mile to town
15 – 22 Mar

Private house rentals

Guest favourite
Home in Ghent
Stylish Hawthorne Valley Farmhouse Retreat
29 June – 6 July
Guest favourite
Home in Catskill
HEAVEN ON EARTH - Hudson Riverfront Home
7 – 14 Jan
Guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
8 – 15 Apr
Guest favourite
Home in Cheshire
Ski at 19th c. Barn in The Berkshires
9 – 16 May
Guest favourite
Home in North Adams
The Lodge @ America’s Switzerland
7 – 14 Nov
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
21 – 28 Sept
Guest favourite
Home in Richmond
LUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
7 – 14 May
Guest favourite
Home in Adams
Mountain View Hideaway
1 – 8 Apr
Guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
28 Apr – 5 May
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires-Near Skis!
16 – 23 Jan
Guest favourite
Home in Pittsfield
Lake/Mountain View Getaway
11 – 18 Aug
Guest favourite
Home in Lee
GreenHouse
6 – 13 May

Quick stats about house rentals in Pittsfield

Total rentals

80 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

2.3K reviews

Nightly prices starting at

$46 AUD before taxes and fees

Destinations to explore