Western Massachusetts holiday homes

We found 1,856 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Western Massachusetts

Showing deals for:8 Jan - 15 Jan

Front of house
Living area
fire pit, bistro lights
Dining room
Exceptional
(14 reviews)

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Amherst

8% off
NZ$13,523
for 7 nights, 1 home
NZ$1,932 per night
includes taxes & fees
Spacious 5-bedroom house steps from UMass Campus, with large backyard.
Interior
Exterior
Interior
Interior
Exceptional
(22 reviews)

Hendee Mansion 5BR Historic Home

Springfield

8% off
NZ$7,160
for 7 nights, 1 home
NZ$1,023 per night
includes taxes & fees
Hendee Mansion 5BR Historic Home
Terrace/patio
House facing lake with deck above, canoe and kayak stored on ground level.
Stairway to landing with one LR couch, barstools, kitchen in background
Property grounds
Exceptional
(170 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis

16% off
NZ$3,324
for 7 nights, 1 home
NZ$475 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Dining
Private kitchen
Interior
Room
Exceptional
(12 reviews)

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

15% off
NZ$3,165
for 7 nights, 1 home
NZ$452 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Exterior detail
Pool
Private kitchen
Interior
Exceptional
(80 reviews)

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

Barre

13% off
NZ$15,438
for 7 nights, 1 home
NZ$2,205 per night
includes taxes & fees
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
Dining
Pool
Exterior
Modern kitchen with Viking stove and extensive collection of pots and pans.
Exceptional
(9 reviews)

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

Colrain

8% off
NZ$11,804
for 7 nights, 1 home
NZ$1,686 per night
includes taxes & fees
1770 House - An end of a dirt road hideaway where you can relax and unwind.
Living area
Interior
Interior
Dining
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
NZ$4,848
for 7 nights, 1 chalet
NZ$693 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Interior
Private kitchen
Exterior
Property grounds
Exceptional
(21 reviews)

Historic Stockbridge Villa on 25 acres

Stockbridge

16% off
NZ$7,933
for 7 nights, 1 villa
NZ$1,133 per night
includes taxes & fees
Historic Stockbridge Villa on 25 acres
10 min. drive to American International College
Interior
Back deck and patio
Private kitchen
Exceptional
(20 reviews)

Longmeadow Ma 3 Bedroom Ranch

Longmeadow

21% off
NZ$4,386
for 7 nights, 1 home
NZ$627 per night
includes taxes & fees
Longmeadow Ma 3 Bedroom Ranch
Independent entrance
Private kitchen
Outdoor dining
Games room
Exceptional
(79 reviews)

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Suffield

8% off
NZ$3,370
for 7 nights, 1 apartment
NZ$481 per night
includes taxes & fees
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Huge wraparound porch is perfect for visiting with family and friends
Beautiful period woodwork and Victorian details
Gourmet kitchen has everything you need to prepare delicious meals
Walk to Spring Street and brand new Williams Bookstore
Exceptional
(158 reviews)

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

Williamstown

7% off
NZ$10,698
for 7 nights, 1 home
NZ$1,528 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Interior
Spring at Jiminy Peak 2019
Night skiing view from living room
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Exceptional
(46 reviews)

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

Hancock

13% off
NZ$16,248
for 7 nights, 1 home
NZ$2,321 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Living room from back staircase
Interior
Second Floor Bedroom #3 - Master Suite (see floor plans as reference)
Exterior
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

7% off
NZ$13,487
for 7 nights, 1 home
NZ$1,927 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Sunroom has Queen pull out sofa bed
The great room with wonderful water views and working fireplace
Hot tub overlooking the lake
Open kitchen to great room, wonderful for cooking and entertaining
Exceptional
(87 reviews)

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

Lee

8% off
NZ$8,366
for 7 nights, 1 home
NZ$1,195 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Interior
Property grounds
Room
Interior
Exceptional
(7 reviews)

Mid-century marvelous 2-bedroom bungalow with lake views in Southwick

Southwick

8% off
NZ$2,588
for 7 nights, 1 home
NZ$370 per night
includes taxes & fees
Mid-century marvelous 2-bedroom bungalow with lake views in Southwick
Living area
Living area
Living area
Interior
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
NZ$8,657
for 7 nights, 1 home
NZ$1,237 per night
includes taxes & fees
The Race Mountain House
Living area
Interior
Dining
Exterior
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,896
for 7 nights, 1 cabin
NZ$699 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Kitchen with stainless steel appliances
Fully screened porch!
Reading nook with natural lighting
Front Staircase
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
NZ$6,970
for 7 nights, 1 home
NZ$996 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Living area
Moose Lodge
Private kitchen
Dining
Exceptional
(54 reviews)

Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge

Great Barrington

8% off
NZ$26,953
for 7 nights, 1 room
NZ$3,850 per night
includes taxes & fees
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Snow-covered house surrounded by evergreens and winter woods.
Main living room with soaring windows overlooking the lake and wooded grounds.
Laundry room with washer, dryer, storage, and a convenient garage entry area.
Landscaped path leading to the front door.
Exceptional
(32 reviews)

Lake View Berkshire Retreat – Private Setting Near Lenox

Lee

15% off
NZ$7,053
for 7 nights, 1 home
NZ$1,008 per night
includes taxes & fees
Lake View Berkshire Retreat – Private Setting Near Lenox
Interior
Interior
Exterior
Room
Exceptional
(44 reviews)

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

Stephentown

8% off
NZ$3,063
for 7 nights, 1 home
NZ$438 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Living area
Outdoor dining
Master bedroom, great view, queen size bed
Dining
Exceptional
(77 reviews)

Awesome Strategic Location Near Smith College

Williamsburg

8% off
NZ$6,201
for 7 nights, 1 home
NZ$886 per night
includes taxes & fees
Awesome Strategic Location Near Smith College
Room
Exterior
Outdoor spa tub
Interior
Exceptional
(22 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
NZ$8,215
for 7 nights, 1 home
NZ$1,174 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Dining
Interior
Living area
Property grounds
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
NZ$12,132
for 7 nights, 1 cabin
NZ$1,733 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)
  • Maple Corner Farm Cross Country Ski Area (17.9 mi / 28.8 km)
  • Olympia Ice Center (20.3 mi / 32.6 km)
  • The Ranch Golf Club (20.4 mi / 32.8 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:

  • 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)
  • Mount Tom (13.9 mi / 22.3 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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