Western Massachusetts holiday homes

We found 1,829 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Western Massachusetts

Showing deals for:20 Nov - 27 Nov

Dining
Interior
Property grounds
Living area
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
NZ$4,657
for 7 nights, 1 chalet
NZ$665 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Dining
Outdoor dining
Interior
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,529
for 7 nights, 1 home
NZ$933 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Enjoy chess, checkers or backgammon
A beautiful brook that runs through our lot
Master 2 Second Floor
Summer view from the lake
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$7,083
for 7 nights, 1 chalet
NZ$1,012 per night
includes taxes & fees
New Lakefront Log Home
Property grounds
Terrace/patio
Dining room with butcher block table
Queen bedroom
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,780
for 7 nights, 1 home
NZ$683 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Exterior
Living area
Private kitchen
Room
Exceptional
(22 reviews)

Brimfield Waterfront cottage

Brimfield

6% off
NZ$3,168
for 7 nights, 1 cottage
NZ$453 per night
includes taxes & fees
Brimfield Waterfront cottage
Private kitchen
Interior
Living area
Interior
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
NZ$5,867
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Dining
Private kitchen
Private kitchen
Property grounds
Exceptional
(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Hancock

20% off
NZ$3,414
for 7 nights, 1 room
NZ$488 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Private kitchen
Pool
Interior
Exterior detail
Exceptional
(77 reviews)

Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!

Barre

13% off
NZ$14,463
for 7 nights, 1 home
NZ$2,066 per night
includes taxes & fees
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
Living area
Exterior
Room
Interior
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
NZ$7,458
for 7 nights, 1 home
NZ$1,065 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Modern kitchen with Viking stove and extensive collection of pots and pans.
Pool
Dining
Exterior
Exceptional
(6 reviews)

1770 House - An end of a dirt road hideaway where you can relax and unwind.

Colrain

8% off
NZ$11,059
for 7 nights, 1 home
NZ$1,580 per night
includes taxes & fees
1770 House - An end of a dirt road hideaway where you can relax and unwind.
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
Build a cozy fire in our wood fireplace, watch the game or play pool!
Exceptional
(154 reviews)

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

Williamstown

7% off
NZ$10,022
for 7 nights, 1 home
NZ$1,432 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Dining area, 10 Chairs are now black, Need a new picture!
View out front door
Early morning summer view
Open Kitchen with a wide open feel
Exceptional
(242 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
NZ$8,970
for 7 nights, 1 home
NZ$1,281 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Property grounds
Private kitchen
Terrace/patio
Living area
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$9,195
for 7 nights, 1 home
NZ$1,314 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
View from entry into living room- perfect spot for relaxing!
Kitchen with counter seating for 4- door on the right to garage
Enclosed porch- view into back yard- dining/game table
Property grounds
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,705
for 7 nights, 1 home
NZ$958 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Master bedroom, great view, queen size bed
Outdoor dining
Dining
Living area
Exceptional
(73 reviews)

Awesome Strategic Location Near Smith College

Williamsburg

8% off
NZ$5,809
for 7 nights, 1 home
NZ$830 per night
includes taxes & fees
Awesome Strategic Location Near Smith College
Interior
Property grounds
Interior
Private kitchen
Exceptional
(81 reviews)

Large Barn styled vacation home that fits groups with space to spare.

Craryville

8% off
NZ$6,991
for 7 nights, 1 home
NZ$999 per night
includes taxes & fees
Large Barn styled vacation home that fits groups with space to spare.
Living area
Terrace/patio
Room
Private kitchen
Exceptional
(20 reviews)

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

Williamstown

12% off
NZ$4,963
for 7 nights, 1 cottage
NZ$709 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,468
for 7 nights, 1 home
NZ$1,067 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Private kitchen
walking distance private beach at lake
walking distance private beach at lake
Living area
Exceptional
(8 reviews)

Lake Congamond Cozy Stylish Comfortable House

Suffield

7% off
NZ$3,726
for 7 nights, 1 home
NZ$532 per night
includes taxes & fees
Lake Congamond Cozy Stylish Comfortable House
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Back patio with Hot Tub
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
NZ$9,603
for 7 nights, 1 home
NZ$1,372 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Exterior
Interior
Property grounds
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,587
for 7 nights, 1 cabin
NZ$655 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
View of the lower deck from the sunroom
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
NZ$8,205
for 7 nights, 1 home
NZ$1,172 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Living area
Interior
Room
Exterior
Exceptional
(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

8% off
NZ$2,840
for 7 nights, 1 home
NZ$406 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Dining
Interior
Property grounds
Exterior
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
NZ$6,791
for 7 nights, 1 cabin
NZ$970 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to lively Western Massachusetts

The area's live music and museums are just some of the reasons to come on holiday to Western Massachusetts. Renowned for its university setting, sporting events and hiking, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Western Massachusetts

Are you looking for attractions to visit in the area? Venture out of your holiday home and experience everything that makes Western Massachusetts a fun spot to go on holiday. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Berkshire East Ski Resort (16.8 mi / 27.1 km)
  • Elements Hot Tub Spa (17.5 mi / 28.2 km)
  • Otis Ridge (17.6 mi / 28.3 km)
  • Olympia Ice Center (20.3 mi / 32.6 km)
  • The Ranch Golf Club (20.4 mi / 32.8 km)
  • Wyndhurst Golf & Club (21.1 mi / 34 km)

Exploring the natural landscape of Western Massachusetts

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Western Massachusetts is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Chesterfield Gorge (2 mi / 3.2 km)
  • Swift River (5.6 mi / 9.1 km)
  • Glendale Falls (5.9 mi / 9.6 km)
  • Look Memorial Park (8.8 mi / 14.1 km)
  • Chapel Brook (9.2 mi / 14.9 km)
  • Smith College Botanic Garden (11.6 mi / 18.7 km)

Transport options to and around Western Massachusetts

Fly into Westfield, MA (BAF-Barnes Municipal), the closest airport, located 15.8 mi (25.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 22.5 mi (36.3 km) away.

If you're travelling by train, Northampton Station, Holyoke Station and Amherst Station are the main stations in the area.

Frequently asked questions

What is the best area to stay in Western Massachusetts when booking a holiday home?
Hancock is one of the most desirable areas to secure a holiday home in Western Massachusetts. Check out our range of comfortable stays and then prepare to discover this destination like a local.
What is the most popular type of holiday home accommodation in Western Massachusetts?
The most popular types of holiday homes in Western Massachusetts are houses. After something a little different? Bookabach has numerous options to match the unique needs of our guests, so you'll see holiday properties in all shapes and sizes. The ideal fit is ready and waiting for you — get yours today.
How much does it cost to rent a holiday home in Western Massachusetts?
A range of factors influence what you'll pay for your holiday home in Western Massachusetts, like the length of stay, type of property and season. Still, all Bookabach homes have something in common — excellent value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Western Massachusetts?
When you travel and the size and style of the property will influence the cost of your beachside stay. Type in your Western Massachusetts travel dates to see your options on Bookabach. Can't live without a hot tub, or maybe a private pool? Use the filters to choose the features and amenities you want.
What are popular home amenities in Western Massachusetts?
When it comes to home amenities that guests are searching for in Western Massachusetts, a microwave oven, a stovetop and a fridge rank the highest. With Bookabach holiday homes, you'll enjoy choices to match your taste and style, whether you're going away with relatives, friends or even pets.
Are there large group holiday homes in Western Massachusetts?
Choose from 135 holiday properties in Western Massachusetts that can accommodate a group of 10 or more people. Whether you're organising a holiday with extended family or an event like an anniversary, there's ample room to get your favourite people together under one roof.
What are the top attractions for families in Western Massachusetts?
Keep your kids busy at these fun family-friendly attractions in Western Massachusetts:
  • Six Flags New England
  • Ski Butternut
  • Jiminy Peak Mountain Resort
Can I find two-bedroom holiday homes in Western Massachusetts?
Choose from 199 two-bedroom holiday properties in Western Massachusetts. Put the kids in the second room or fill it with a couple of your favourite people. There's plenty of space for whoever's fortunate enough to be joining your adventure.
Are there holiday homes with WiFi in Western Massachusetts?
Western Massachusetts has 311 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to posting pics on social media, these Bookabach homes will keep you online.
How old do you have to be to rent a holiday home in Western Massachusetts?
The minimum required age is generally 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your preferred Western Massachusetts holiday home before booking.
How long can I rent a holiday home in Western Massachusetts for?
The length of time you can book a holiday home in Western Massachusetts differs according to the property. Simply enter your selected travel dates to see a list of options offering extended stays. With lots of creature comforts such as washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere just right to call your home away from home in Western Massachusetts.

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