Holiday homes & B&B in Pittsfield
Choose the right place for you
FACILITIES
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Wi-Fi
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Non Smoking Only
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Pets Allowed
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
DISTANCE FROM CENTRE
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Less than 1 km
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Less than 3 km
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Less than 5 km
Holiday rental deals in Pittsfield
We have selected the best vacation rentals in Pittsfield. Save money with Bluepillow by comparing the best deals from major travel websites in Pittsfield
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Pittsfield - United States
2/BR Historic District-Long Term Rentals Welcome!
- 4 Guests 2Bedrooms
10 Exceptional (6)This apartment is located in Pittsfield. Berkshire Museum and Colonial Theater are cultural highlights, and some of the area's activities can be experienced at Bousquet Ski Area and Kennedy Park. The Bookstore ...Check Availability -
Pittsfield - United States
Apartment Newly Remodeled Super Location
- 4 Guests 2Bedrooms
10 Exceptional (5)This apartment is located in Pittsfield. Colonial Theater and Herman Melville's Arrowhead are local landmarks, and travelers looking to shop may want to visit Guido's Marketplace and Lee Premium Outlets. ...Check Availability -
Pittsfield - United States
Available for Healthcare and long term stays welcome 3 miles from Hospital
- 4 Guests 1Bedroom
10 Exceptional (3)This apartment is located in Lanesborough. Crane Museum of Papermaking and Barrington Stage Company are cultural highlights, and some of the area's attractions include Berkshire Museum and Bousquet Ski ...Check Availability -
Pittsfield - United States
MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!!
- 6 Guests 3Bedrooms
10 Exceptional (9)Located in Pittsfield, MEMORIAL DAY WEEK THRU 6/30 AVAILABLE!!! is in the mountains. Herman Melville's Arrowhead and Colonial Theater are local landmarks, and some of the area's activities can be experienced ...Check Availability -
Pittsfield - United States
2/BR Historic District Apartment
- 4 Guests 2Bedrooms
9 Exceptional (2)This apartment is located in Pittsfield. Colonial Theater and Herman Melville's Arrowhead are local landmarks, and some of the area's activities can be experienced at Bousquet Ski Area and Kennedy Park. ...Check Availability -
Pittsfield - United States
Apartment Newly Remodeled Super Location
- 4 Guests 2Bedrooms
10 Exceptional (10)This apartment is located in Pittsfield. Colonial Theater and Herman Melville's Arrowhead are local landmarks, and travelers looking to shop may want to visit Guido's Marketplace and Lee Premium Outlets. ...Check Availability -
Pittsfield - United States
Available for Winter Rental, Healthcare, Central
- 6 Guests 2Bedrooms
8.6 Fabulous (12)This apartment is located in Lanesborough. Crane Museum of Papermaking and Barrington Stage Company are cultural highlights, and some of the area's landmarks include Colonial Theater and Crane Museum of ...Check Availability -
Pittsfield - United States
Berkshire Mountain Lodge
- Hotel
6.8 Pleasant (881)Featuring an indoor swimming pool and a fitness centre, Berkshire Mountain Lodge is located in Pittsfield. Free WiFi access is available in this lodge. A full kitchen, sofa bed and flat-screen cable TV ...Check Availability -
Pittsfield - United States
Condo Resort in Cultural Art Haven, Berkshire
- 4 Guests 1Bedroom
This condo is located in Pittsfield. Herman Melville's Arrowhead and Arrowhead Museum are cultural highlights, and travelers looking to shop may want to visit Guido's Marketplace and Lee Premium Outlets. ...Check Availability -
Pittsfield - United States
Family Vacation Mountain Lodge for all seasons...
- 4 Guests 1Bedroom
This lodge is located in Pittsfield. Norman Rockwell Museum and Arrowhead Museum are cultural highlights, and some of the area's attractions include Bousquet Ski Area and Berkshire Museum. Traveling with ...Check Availability -
Pittsfield - United States
Lakeside Berkshires Home Near Hiking and Skiing!
- 30 Guests 10Bedrooms
5.3 Pleasant (9)Check Availability -
Pittsfield - United States
Perfect for Winter Skiing!!
- 8 Guests 4Bedrooms
This condo is located in Pittsfield. Bousquet Ski Area and Berkshire Museum are local attractions and those in the mood for shopping can visit Guido's Marketplace and Lee Premium Outlets. The Bookstore ...Check Availability -
Pittsfield - United States
Berkshire Cottage
- 12 Guests 4Bedrooms
Berkshire Cottage is located in Lanesborough and offers barbecue facilities. The property has mountain views. The holiday home is fitted with 5 bedrooms, a kitchen with a dishwasher and an oven, and ...Check Availability -
Pittsfield - United States
Charming Historic Home Close to Downtown and Skiing!
- 10 Guests 5Bedrooms
7.6 Very Good (26)Charming Historic Home Close to Downtown and Skiing! is situated in Pittsfield, 12 km from Tanglewood, 13 km from Cranwell Spa & Golf Club, as well as 13 km from Tanglewood Musical Center. ...Check Availability -
Pittsfield - United States
Charming Apartment In Berkshire Victorian Home
- 7 Guests 3Bedrooms
Located in Pittsfield, this apartment is in the city center and in the mountains. Berkshire Museum and Colonial Theater are cultural highlights, and some of the area's attractions include Bousquet Ski ...Check Availability -
Pittsfield - United States
Spacious Historic Home in the Berkshires!
- 9 Guests 5Bedrooms
Set in Pittsfield, 12 km from Tanglewood, 13 km from Cranwell Spa & Golf Club and 13 km from Tanglewood Musical Center, Spacious Historic Home in the Berkshires! offers accommodation with a balcony and ...Check Availability -
Pittsfield - United States
Serene Retreat in the Scenic Berkshire Mountains
- 4 Guests 1Bedroom
Located in Pittsfield, this condo is in the mountains. Arrowhead Museum and Herman Melville's Arrowhead are cultural highlights, and travelers looking to shop may want to visit Guido's Marketplace and ...Check Availability -
Pittsfield - United States
Berkshire Mountainside Condo
- 8 Guests 3Bedrooms
Berkshire Mountainside Condo is located in Pittsfield. Guido's Marketplace and Lee Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural ...Check Availability -
Pittsfield - United States
Cozy Renovated with 1 parking space
- 2 Guests 1Bedroom
This apartment is located in Pittsfield. Guido's Marketplace and Lee Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can ...Check Availability -
Pittsfield - United States
Beautiful, Newly Renovated Apartment in a Great Location
- 2 Guests 1Bedroom
This apartment is located in Pittsfield. Berkshire Museum and Colonial Theater are cultural highlights, and some of the area's attractions include Bousquet Ski Area and The Bookstore. Berkshire Scenic ...Check Availability
Hotels in Pittsfield, our top selection just for you
Are you looking for hotels in Pittsfield? Here is a selection of the best hotels in Pittsfield
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Pittsfield - United States
Hampton Inn & Suites Berkshires-Lenox
- Hotel
9.2 Exceptional (2862)Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Arrowhead Museum. This hotel is 4.5 mi (7.3 km) from Tanglewood Music ...Check Availability -
Pittsfield - United States
The Weathervane Motel
- Hotel
7.1 Very Good (256)The Weathervane Motel is located in Lanesborough. Berkshire Athenaeum and Berkshire Museum are cultural highlights, or if an activity is on the agenda, check out Bousquet Ski Area. Spend some time exploring ...Check Availability -
Pittsfield - United States
Knights Inn Lenox
- Hotel
8 Fabulous (8)Ideally located in the East Lenox area, Knights Inn Lenox promises a relaxing and wonderful visit. The property offers a wide range of amenities and perks to ensure you have a great time. Service-minded ... -
Pittsfield - United States
The Yankee, Trademark Collection by Wyndham
- Hotel
8.9 Fabulous (2556)Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in October ... -
Pittsfield - United States
Best Western Plus Berkshire Hills Inn & Suites
- Hotel
8.3 Fabulous (2585)Located off Route 20, this Pittsfield hotel is 3.6 miles from Lichtenstein Center for the Arts. The hotel features a hydromassage tub and a gym as well as traditional rooms with free WiFi. ... -
Pittsfield - United States
Hilton Garden Inn Lenox Pittsfield
- Hotel
9.2 Exceptional (1138)Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodation in Pittsfield. The hotel has a fitness centre and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar. All ... -
Pittsfield - United States
Berkshire Inn
- Hotel
7.6 Very Good (1425)Located in the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi. The Bousquet Ski Area is only an 8-minute drive away. ... -
Pittsfield - United States
Howard Johnson by Wyndham Lenox
- Hotel
5.4 Pleasant (1783)This Lenox, Massachusetts hotel is just one mile from Bousquet Ski Area. Howard Johnson Lenox offers an outdoor pool, mountain views and guest rooms with free Wi-Fi and cable TV. Rooms are furnished with ... -
Pittsfield - United States
The Central Downtown Inn Suites
- Hotel
8.9 Fabulous (28)Offering suites with a deck or patio, this hotel is located in the heart of the Pittsfield city centre, walking distance from numerous shops and restaurants. The Berkshire Museum is 350 metres away. ... -
Pittsfield - United States
Wagon Wheel Inn
- Hotel
7.4 Very Good (1201)This Massachusetts motel offers rooms with free Wi-Fi and a 24-hour front desk. The motel is within a 5-minute drive of the Arrowhead Museum, former home of Herman Meville. ... -
Pittsfield - United States
Lenox Inn
- Hotel
7.2 Very Good (116)This Lenox motel offers free Wi-Fi and rooms equipped with a refrigerator and cable TV. A table with chairs is also included. Bousquet Ski Area is 1 miles away. A hair dryer and a telephone are offered ... -
Pittsfield - United States
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
- Hotel
7.6 Very Good (1103)Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts. We are 10 minutes driving time to many corporations such as General Dynamics, Lenco Armored ... -
Pittsfield - United States
Econo Lodge Pittsfield
- Hotel
5.3 Pleasant (1662)Econo Lodge Pittsfield is located in the heart of Pittsfield near several major highways, including Route 90. This hotel offers easy access to Berkshire Opera Co. and Battle Brook Park. ... -
Pittsfield - United States
Knights Inn Lenox
- Hotel
5.9 Pleasant (872)This hotel in Lenox, Massachusetts is a 10-minute drive to the Edith Wharton Estate-The Mount. The hotel has free Wi-Fi and on-site parking. Rooms at Knights Inn Lenox include cable TV, ironing facilities ... -
Pittsfield - United States
HOTEL ON NORTH
- Hotel
9.4 Exceptional (1022)Hotel on North is a 45-room boutique hotel elegantly transformed within a pair of historic buildings. Filled with custom furniture from local artisans and craftspeople Hotel on North celebrates the creative ...Check Availability -
Pittsfield - United States
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Pittsfield - United States
Weathervane Motel Lanesboro
- Hotel
Set in a prime location of Lanesboro (MA), Weathervane Motel Lanesboro puts everything the city has to offer just outside your doorstep. Offering a variety of facilities and services, the hotel provides ...Check Availability
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Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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![Farmstays in Pittsfield]()
Farmstays in Pittsfield -
![Hotels in Pittsfield]()
Hotels in Pittsfield
The best hotels with swimming pool in Pittsfield
Book your relaxing holiday, by choosing the best deals at hotels with swimming pools in Pittsfield
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Pittsfield - United States
Hampton Inn & Suites Berkshires-Lenox
- Hotel
9.2 Exceptional (2862)Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Arrowhead Museum. This hotel is 4.5 mi (7.3 km) from Tanglewood Music ...Check Availability -
Pittsfield - United States
The Weathervane Motel
- Hotel
7.1 Very Good (256)The Weathervane Motel is located in Lanesborough. Berkshire Athenaeum and Berkshire Museum are cultural highlights, or if an activity is on the agenda, check out Bousquet Ski Area. Spend some time exploring ...Check Availability -
Pittsfield - United States
Knights Inn Lenox
- Hotel
8 Fabulous (8)Ideally located in the East Lenox area, Knights Inn Lenox promises a relaxing and wonderful visit. The property offers a wide range of amenities and perks to ensure you have a great time. Service-minded ... -
Pittsfield - United States
The Yankee, Trademark Collection by Wyndham
- Hotel
8.9 Fabulous (2556)Nestled on a 111-acre wildlife sanctuary and surrounded by the beauty of the Berkshires, The Yankee, Trademark Collection by Wyndham provides a welcoming stay by the famous Appalachian Trail in October ... -
Pittsfield - United States
Best Western Plus Berkshire Hills Inn & Suites
- Hotel
8.3 Fabulous (2585)Located off Route 20, this Pittsfield hotel is 3.6 miles from Lichtenstein Center for the Arts. The hotel features a hydromassage tub and a gym as well as traditional rooms with free WiFi. ... -
Pittsfield - United States
Hilton Garden Inn Lenox Pittsfield
- Hotel
9.2 Exceptional (1138)Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodation in Pittsfield. The hotel has a fitness centre and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar. All ... -
Pittsfield - United States
Berkshire Inn
- Hotel
7.6 Very Good (1425)Located in the heart of the Berkshire Mountains, this family-owned motel features an outdoor pool and free Wi-Fi. The Bousquet Ski Area is only an 8-minute drive away. ... -
Pittsfield - United States
Howard Johnson by Wyndham Lenox
- Hotel
5.4 Pleasant (1783)This Lenox, Massachusetts hotel is just one mile from Bousquet Ski Area. Howard Johnson Lenox offers an outdoor pool, mountain views and guest rooms with free Wi-Fi and cable TV. Rooms are furnished with ... -
Pittsfield - United States
The Central Downtown Inn Suites
- Hotel
8.9 Fabulous (28)Offering suites with a deck or patio, this hotel is located in the heart of the Pittsfield city centre, walking distance from numerous shops and restaurants. The Berkshire Museum is 350 metres away. ... -
Pittsfield - United States
Wagon Wheel Inn
- Hotel
7.4 Very Good (1201)This Massachusetts motel offers rooms with free Wi-Fi and a 24-hour front desk. The motel is within a 5-minute drive of the Arrowhead Museum, former home of Herman Meville. ... -
Pittsfield - United States
Lenox Inn
- Hotel
7.2 Very Good (116)This Lenox motel offers free Wi-Fi and rooms equipped with a refrigerator and cable TV. A table with chairs is also included. Bousquet Ski Area is 1 miles away. A hair dryer and a telephone are offered ... -
Pittsfield - United States
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
- Hotel
7.6 Very Good (1103)Welcome to the Holiday Inn and Suites Pittsfield-Berkshires Centrally located in downtown Pittsfield Massachusetts. We are 10 minutes driving time to many corporations such as General Dynamics, Lenco Armored ... -
Pittsfield - United States
Econo Lodge Pittsfield
- Hotel
5.3 Pleasant (1662)Econo Lodge Pittsfield is located in the heart of Pittsfield near several major highways, including Route 90. This hotel offers easy access to Berkshire Opera Co. and Battle Brook Park. ... -
Pittsfield - United States
Knights Inn Lenox
- Hotel
5.9 Pleasant (872)This hotel in Lenox, Massachusetts is a 10-minute drive to the Edith Wharton Estate-The Mount. The hotel has free Wi-Fi and on-site parking. Rooms at Knights Inn Lenox include cable TV, ironing facilities ... -
Pittsfield - United States
HOTEL ON NORTH
- Hotel
9.4 Exceptional (1022)Hotel on North is a 45-room boutique hotel elegantly transformed within a pair of historic buildings. Filled with custom furniture from local artisans and craftspeople Hotel on North celebrates the creative ...Check Availability -
Pittsfield - United States
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Pittsfield - United States
Weathervane Motel Lanesboro
- Hotel
Set in a prime location of Lanesboro (MA), Weathervane Motel Lanesboro puts everything the city has to offer just outside your doorstep. Offering a variety of facilities and services, the hotel provides ...Check Availability
B&Bs and holiday homes Pittsfield: the best accommodation solutions
Pittsfield is a very appreciated destination by the world's tourists. The 9,337 reviews written for all the accommodation in the area are the proof: 3,409 reviews with a score of 10.0 Excellent and 1,411 reviews with a score of 8.0 Very Good. Reading these opinions you can learn which are the best accommodations with the best reviews in Pittsfield.
The best solutions for accommodation available in the area are many. Over a total of 165 accommodation, it is possible to distinguish 119 apartments, 26 hotels, 2 b&bs, 89 independent homes, 13 villas and much more. Amongst these you will be able to find the best offers for the best solution for your needs, wether you decide to go alone, for a romantic get-away, or with a group of friends. The end goal is an unforgettable holiday in Pittsfield.
Every type of accommodation at this destination displays a range of services that will adapt perfectrly to your needs: Pets Allowed, Pool, Kitchen, Spa, Parking and much more. The choice is yours.
- Here you can find the best accommodation in Pittsfield
- The best apartments in Pittsfield
- The best B&Bs in Pittsfield
- The best hotels in Pittsfield
- The best independent houses in Pittsfield
- The best holiday farm houses in Pittsfield
- The best villas in Pittsfield
- The best low cost tariffs in Pittsfield
Pittsfield: How much does accommodation cost?
How much does holiday accommodation cost in Pittsfield? On average in Pittsfield it is possible to find accommodation solutions for an average cost of 243 pounds per night.
The main interest points and what to see in Pittsfield during your stay
The best accommodation in Pittsfield can be found near the main interest points.
Not far from the centre you can find 165 accommodation available with the best offers: 119 Apartments, 2 B&Bs, 26 Hotels, and much more.
Below you can find the best apartments near the centre.
Pittsfield: Which is the ideal month for a holiday?
Pittsfield: when to go? Whether you love the heat or the cold, if you're planning a trip here, it could be useful for you to know: July, has temperatures that can reach 26°C, it's the hottest month at this touristic destination. January instead is the coldest month, where temperatures can trop to -1°C.
