Pittsfield holiday rentals

We found 1,006 holiday rentals — enter your dates for availability
Discover a selection of 37 homes and other holiday rentals in Pittsfield that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Pittsfield

Showing deals for:18 Dec - 25 Dec

Exterior
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
AU$3,409
for 7 nights, 1 cottage
AU$487 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
View from the lawn by the water
view from the 2nd bedroom
Workstation with a view!
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$7,969
for 7 nights, 1 home
AU$1,138 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Dining
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,462
for 7 nights, 1 home
AU$923 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Kitchen open to living room
Kitchen
2nd bedroom
Patio off kitchen
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
AU$2,327
for 7 nights, 1 cottage
AU$332 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Terrace/patio
Private kitchen
Living area
Property grounds
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,893
for 7 nights, 1 home
AU$1,128 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Walk to Spring Street and brand new Williams Bookstore
Beautiful period woodwork and Victorian details
Gourmet kitchen has everything you need to prepare delicious meals
Huge wraparound porch is perfect for visiting with family and friends
Exceptional
(157 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
AU$8,383
for 7 nights, 1 home
AU$1,198 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Interior
Living area
Interior
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,320
for 7 nights, 1 home
AU$903 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Living area
Terrace/patio
Dining
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

16% off
AU$4,391
for 7 nights, 1 cottage
AU$627 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Reading nook with natural lighting
Fully screened porch!
Kitchen with stainless steel appliances
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$5,158
for 7 nights, 1 home
AU$737 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Property grounds
Interior
Exterior
Dining
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,784
for 7 nights, 1 cabin
AU$541 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Staircase
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
Outdoor dining and grill on the 16' x 20' wooden deck.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$5,458
for 7 nights, 1 home
AU$780 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Second story deck with lake views, dining table for 8, sitting area and grill
Open and bright main floor living space with stunning views of Laurel Lake.
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,447
for 7 nights, 1 home
AU$778 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
View of the river.
Porch opens up from dining room. Ceiling fan and lights above.
Entrance view.
Game, puzzle and play table - plenty of chairs.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
AU$2,828
for 7 nights, 1 home
AU$404 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Dining
Outdoor dining
Interior
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
AU$5,899
for 7 nights, 1 home
AU$843 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Living area
Interior
Interior
Exterior
Exceptional
(42 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
AU$2,392
for 7 nights, 1 home
AU$342 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Screened in porch
Terrace/patio
Dining room with butcher block table
Property grounds
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
AU$3,966
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Large Smart HDTV with electric fireplace in living room, showing dining room
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Views from the back of the 16 acres on the property
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
AU$3,548
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Private kitchen
Outdoor dining
Exterior detail
Room
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$4,022
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Alfresco dining
River view from window
Blue House side entry from driveway
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,820
for 7 nights, 1 home
AU$546 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Spring at Jiminy Peak 2019
Night skiing view from living room
Interior
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
AU$12,670
for 7 nights, 1 home
AU$1,810 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Enjoy a beautiful crisp night under the lights
After a hard day on the trails or a long day on the town, relax in this oasis
Seamless entertaining with the wide open concept, living room -kitchen- patio
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
AU$6,443
for 7 nights, 1 home
AU$920 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,414
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Terrace/patio
Living area
Living area
Private kitchen
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
AU$5,587
for 7 nights, 1 home
AU$798 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Exterior
Interior
Room
Living area
Exceptional
(61 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,647
for 7 nights, 1 apartment
AU$235 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the lakeside setting in Pittsfield

Take a holiday to Pittsfield and enjoy the area's entertainment, theatre scene and opera. This city's baseball games, museums and cycling draw many visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Pittsfield

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Pittsfield a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (2.6 mi / 4.3 km)
  • Wyndhurst Golf & Club (7.3 mi / 11.8 km)
  • Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
  • Waubeeka Golf Links (14.4 mi / 23.2 km)
  • Ski Butternut (18.7 mi / 30 km)
  • Otis Ridge (19.2 mi / 30.8 km)

Exploring the natural landscape of Pittsfield

Whether you're an active traveller or just want to take in the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Pontoosuc Lake (3.3 mi / 5.3 km)
  • Lenox Mountain (4.2 mi / 6.8 km)
  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • Wahconah Falls State Park (7.6 mi / 12.3 km)
  • The Mount (7.9 mi / 12.8 km)
  • Stockbridge Bowl (8.5 mi / 13.7 km)

Transport options to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you're travelling by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

Frequently asked questions

What is the best area to stay in Pittsfield when booking a holiday rental?
When considering a holiday rental in Pittsfield, Massachusetts, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming mix of historical architecture and modern amenities, making it a delightful base for exploring the region. You'll find a variety of properties available, from cosy apartments to more spacious homes, suiting different group sizes and preferences.Staying downtown puts you within walking distance of several attractions, such as the Berkshire Museum, which features a fascinating collection of art, history, and natural sciences. Additionally, the nearby Colonial Theatre regularly hosts a range of performances, adding to the cultural richness of the area. For those who enjoy outdoor activities, the nearby Pittsfield State Forest offers numerous hiking trails and beautiful natural scenery.Another appealing neighbourhood is the Morningside area, known for its lovely residential streets and proximity to public parks. Here, you can find properties that provide a more suburban feel while still being close to the city's amenities. The Morningside area is also near Burbank Park, which features scenic walking paths and recreational facilities.
Where are the best Pittsfield ski resort rentals?
For those seeking ski resort rentals near Pittsfield, Massachusetts, the nearby Jiminy Peak Mountain Resort is a top choice. Located just a short drive away in Hancock, this ski area offers a variety of accommodation options, including condos and chalets that cater to families and groups. Many of these properties come equipped with essential amenities, such as full kitchens, spacious living areas, and often access to communal facilities like hot tubs and heated pools, great for relaxing after a day on the slopes.In Pittsfield itself, visitors can find charming rental homes and apartments that provide a cozy base for exploring the region. Some of these properties feature amenities like fireplaces, outdoor decks, and proximity to local dining and shopping, enhancing the overall experience. The city is also known for its cultural attractions, with nearby galleries and theatres, making it an ideal spot for those who enjoy both winter sports and arts.For outdoor enthusiasts, the surrounding Berkshire Mountains offer additional hiking and recreational opportunities during the off-season, ensuring that there's plenty to explore beyond skiing.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, holiday houses are the most popular type of holiday rental, with around 136 available throughout the area. These houses typically offer spacious living environments suitable for families or groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces for relaxation. Many are located in residential neighbourhoods, providing a tranquil setting close to local attractions like the Berkshire Museum and the scenic Pittsfield State Forest. Additionally, there are about 20 apartments, which provide a more compact and convenient option for couples or solo travellers, often including amenities like kitchenettes and living areas. Condos and cottages, with around 12 each, also add variety to the rental landscape, suiting different preferences.
Are there any family house rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous family-friendly house rentals available, with around 32 options scattered throughout the city. The neighbourhoods offer a variety of accommodations, many of which feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to play. Amenities such as Wi-Fi and laundry facilities are commonly included, ensuring a comfortable stay for families.Visitors will find that Pittsfield is conveniently located near attractions like the Berkshire Museum, which offers engaging exhibits for all ages, and the nearby Bousquet Mountain, where families can enjoy outdoor activities year-round. The surrounding scenic beauty of the Berkshires also provides ample opportunities for hiking and exploring nature, making it an ideal destination for those seeking both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Pittsfield?
In Pittsfield, Massachusetts, several holiday homes are available for rent that feature pools and hot tubs, making it a delightful option for those seeking relaxation during their stay. The area offers a variety of neighbourhoods, each with its unique charm. Properties can be found in residential areas that provide a peaceful atmosphere, ideal for families or groups looking to unwind.Travellers can expect various amenities in these rentals, including private pools and hot tubs, spacious outdoor patios, and fully equipped kitchens for self-catering. Some homes may also include features such as game rooms or large gardens, enhancing the overall experience.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, there are numerous pet-friendly house rentals available, offering a variety of options for those travelling with furry companions. Many of these rentals are equipped with comfortable living spaces, fully stocked kitchens, and outdoor areas where pets can roam. The properties often feature amenities such as fenced yards, making them ideal for both relaxation and play.The city is in close proximity to several parks that welcome pets, including Burbank Park, which offers walking trails and scenic views of the water, great for leisurely strolls with your dog. Additionally, the nearby Pittsfield State Forest provides ample opportunities for hiking and exploring nature, with its extensive trails and beautiful landscapes.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Massachusetts, there are numerous remote work holiday rentals available, with around 176 options to choose from. This charming city offers a variety of accommodations that cater to those needing to balance work and leisure. Many of these properties come equipped with dedicated office spaces, high-speed internet, and amenities such as Wi-Fi in rooms and access to printers, making them ideal for remote workers.Located in the beautiful Berkshire region, these rentals often feature comfortable living areas and fully equipped kitchens, allowing for a pleasant and productive stay. The area is rich in cultural attractions, including museums and theatres, and offers outdoor activities such as hiking and skiing in the nearby mountains. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pittsfield?
In Pittsfield, popular rental amenities include kitchens, fireplaces, and onsite parking, making it convenient for guests to settle in comfortably. Many properties also feature coffee and tea makers for a warm beverage after a day of exploring the area. Additionally, outdoor spaces such as decks or patios are common, providing a pleasant spot for relaxation and enjoying the fresh air.
When is the best time to visit Pittsfield for a holiday rental?
The peak travel season in Pittsfield runs from June to August, with July being the most popular month. This vibrant period attracts visitors looking to immerse themselves in outdoor activities, cultural events, and the stunning natural beauty of the Berkshires. With warm temperatures averaging between 20 and 30 degrees Celsius, it's the superb time to explore the area's hiking trails, visit art galleries, or attend local festivals.During the summer months, you can enjoy a range of activities, from boating on nearby lakes to attending concerts in the park. The lively option makes it an ideal choice for families and groups seeking memorable experiences together.For those considering a more budget-friendly option, visiting in December can be a great choice. Although it falls outside the main tourist season, the charm of Pittsfield during the winter months offers unique attractions, such as holiday festivities and a quieter pace for exploring the town's historical sites. It's a delightful time to enjoy the beauty of the Berkshires dusted in snow.
What are the top attractions in Pittsfield?
In Pittsfield, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural heritage. The Berkshire Museum, located in the downtown area, features a diverse collection of art, science, and historical exhibits, making it a great stop for families and art enthusiasts alike. Nearby, the historic Colonial Theatre hosts various performances, including concerts and plays, contributing to the local cultural scene.For outdoor enthusiasts, the nearby Pittsfield State Forest offers an array of hiking and biking trails, as well as opportunities for fishing and wildlife observation, making it a superb destination for those looking to immerse themselves in nature. Additionally, the stunning views from the summit of Mount Greylock, the highest peak in Massachusetts, are just a short drive away, providing ample opportunities for hiking and photography.In the summer, the city's parks, such as Burbank Park on Pontoosuc Lake, offer recreational activities including swimming, boating, and picnicking.
Are all fees included in the Pittsfield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pittsfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pittsfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pittsfield holiday homes?
You can find great discounts on holiday homes in Pittsfield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pittsfield holiday home booking on Stayz?
To find Pittsfield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pittsfield?
A long-stay holiday home in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pittsfield holiday home?
Book your Pittsfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday homes in Pittsfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pittsfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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