Western Massachusetts holiday rentals

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

Living area
Interior
Dining
Property grounds
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
AU$3,794
for 7 nights, 1 chalet
AU$542 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Dining
Outdoor dining
Property grounds
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

21% off
AU$5,360
for 7 nights, 1 home
AU$766 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Summer view from the lake
A beautiful brook that runs through our lot
Enjoy chess, checkers or backgammon
Master 2 Second Floor
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
AU$5,827
for 7 nights, 1 chalet
AU$832 per night
includes taxes & fees
New Lakefront Log Home
Property grounds
Terrace/patio
Screened in porch
Queen bedroom
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,894
for 7 nights, 1 home
AU$556 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Living area
Living area
Exterior
Private kitchen
Exceptional
(22 reviews)

Brimfield Waterfront cottage

Brimfield

6% off
AU$2,655
for 7 nights, 1 cottage
AU$379 per night
includes taxes & fees
Brimfield Waterfront cottage
Pool
Interior
Interior
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,814
for 7 nights, 1 home
AU$688 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Dining
Private kitchen
Property grounds
Private kitchen
Exceptional
(5 reviews)

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

Hancock

20% off
AU$2,859
for 7 nights, 1 room
AU$408 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Interior
Pool
Exterior detail
Private kitchen
Exceptional
(77 reviews)

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

Barre

13% off
AU$12,094
for 7 nights, 1 home
AU$1,728 per night
includes taxes & fees
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
Room
Exterior
Interior
Outdoor spa tub
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,144
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Interior
Pool
Dining
Exterior
Exceptional
(6 reviews)

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

Colrain

8% off
AU$9,070
for 7 nights, 1 home
AU$1,296 per night
includes taxes & fees
1770 House - An end of a dirt road hideaway where you can relax and unwind.
Gourmet kitchen has everything you need to prepare delicious meals
Beautiful period woodwork and Victorian details
Huge wraparound porch is perfect for visiting with family and friends
Walk to Spring Street and brand new Williams Bookstore
Exceptional
(154 reviews)

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

Williamstown

7% off
AU$8,221
for 7 nights, 1 home
AU$1,174 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
View from Kitchen sink
Exceptional
(242 reviews)

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

Wilmington

8% off
AU$7,350
for 7 nights, 1 home
AU$1,050 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Terrace/patio
Private kitchen
Living area
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,535
for 7 nights, 1 home
AU$1,076 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Property grounds
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
Enclosed porch- view into back yard- dining/game table
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,510
for 7 nights, 1 home
AU$787 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Living area
Outdoor dining
View from Deck to Pool
Master bedroom, great view, queen size bed
Exceptional
(73 reviews)

Awesome Strategic Location Near Smith College

Williamsburg

8% off
AU$4,765
for 7 nights, 1 home
AU$681 per night
includes taxes & fees
Awesome Strategic Location Near Smith College
Interior
Property grounds
Interior
Exterior
Exceptional
(81 reviews)

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

Craryville

8% off
AU$5,749
for 7 nights, 1 home
AU$821 per night
includes taxes & fees
Large Barn styled vacation home that fits groups with space to spare.
Dining
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

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

Williamstown

12% off
AU$4,045
for 7 nights, 1 cottage
AU$578 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Interior
Living area
Interior
Outdoor dining
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,154
for 7 nights, 1 home
AU$879 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Exterior
walking distance private beach at lake
Living area
walking distance private beach at lake
Exceptional
(8 reviews)

Lake Congamond Cozy Stylish Comfortable House

Suffield

7% off
AU$3,097
for 7 nights, 1 home
AU$442 per night
includes taxes & fees
Lake Congamond Cozy Stylish Comfortable House
Add a touch of warmth and charm to your dining experience!
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
AU$7,874
for 7 nights, 1 home
AU$1,125 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Property grounds
Interior
Dining
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,737
for 7 nights, 1 cabin
AU$534 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View of the lower deck from the sunroom
View from the lawn by the water
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,773
for 7 nights, 1 home
AU$968 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior
Interior
Interior
Room
Exceptional
(40 reviews)

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

Stephentown

8% off
AU$2,378
for 7 nights, 1 home
AU$340 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Exterior
Interior
Dining
Living area
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$5,582
for 7 nights, 1 cabin
AU$797 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? Stayz 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 Stayz 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 Stayz. 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 Stayz 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 Stayz 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 Stayz, 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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