Western Massachusetts holiday rentals

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

Dining room
Living area
Front of house
kitchen
Exceptional
(14 reviews)

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

Amherst

8% off
AU$10,408
for 7 nights, 1 home
AU$1,487 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
AU$5,670
for 7 nights, 1 home
AU$810 per night
includes taxes & fees
Hendee Mansion 5BR Historic Home
Stairway to landing with one LR couch, barstools, kitchen in background
House facing lake with deck above, canoe and kayak stored on ground level.
Property grounds
Terrace/patio
Exceptional
(170 reviews)

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

East Otis

16% off
AU$2,683
for 7 nights, 1 home
AU$383 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Dining
Private kitchen
Room
Living area
Exceptional
(12 reviews)

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

Windsor Locks

15% off
AU$2,554
for 7 nights, 1 home
AU$365 per night
includes taxes & fees
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Interior
Pool
Interior
Private kitchen
Exceptional
(80 reviews)

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

Barre

13% off
AU$12,445
for 7 nights, 1 home
AU$1,778 per night
includes taxes & fees
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
Exterior
Pool
Modern kitchen with Viking stove and extensive collection of pots and pans.
Dining
Exceptional
(9 reviews)

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

Colrain

8% off
AU$9,333
for 7 nights, 1 home
AU$1,333 per night
includes taxes & fees
1770 House - An end of a dirt road hideaway where you can relax and unwind.
Living area
Interior
Dining
Property grounds
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
AU$3,808
for 7 nights, 1 chalet
AU$544 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
Property grounds
Private kitchen
Interior
Exterior
Exceptional
(21 reviews)

Historic Stockbridge Villa on 25 acres

Stockbridge

16% off
AU$6,350
for 7 nights, 1 villa
AU$907 per night
includes taxes & fees
Historic Stockbridge Villa on 25 acres
Private kitchen
Interior
10 min. drive to American International College
Back deck and patio
Exceptional
(20 reviews)

Longmeadow Ma 3 Bedroom Ranch

Longmeadow

21% off
AU$3,515
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
Longmeadow Ma 3 Bedroom Ranch
Outdoor dining
Private kitchen
Games room
Property grounds
Exceptional
(79 reviews)

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

Suffield

8% off
AU$2,718
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Walk to Spring Street and brand new Williams Bookstore
Beautiful period woodwork and Victorian details
Build a cozy fire in our wood fireplace, watch the game or play pool!
Gourmet kitchen has everything you need to prepare delicious meals
Exceptional
(158 reviews)

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

Williamstown

7% off
AU$8,459
for 7 nights, 1 home
AU$1,208 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
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$13,093
for 7 nights, 1 home
AU$1,870 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Second Floor Bedroom #3 - Master Suite (see floor plans as reference)
Interior
Living room from back staircase
Exterior
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
AU$10,379
for 7 nights, 1 home
AU$1,483 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Dining
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
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
AU$6,697
for 7 nights, 1 home
AU$957 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Interior
Property grounds
Room
Private kitchen
Exceptional
(7 reviews)

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

Southwick

8% off
AU$2,121
for 7 nights, 1 home
AU$303 per night
includes taxes & fees
Mid-century marvelous 2-bedroom bungalow with lake views in Southwick
Interior
Living area
Living area
Lobby
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
AU$6,886
for 7 nights, 1 home
AU$984 per night
includes taxes & fees
The Race Mountain House
Living area
Interior
Exterior
Dining
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,921
for 7 nights, 1 cabin
AU$560 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Reading nook with natural lighting
Fully screened porch!
Dining Room w/ Doors to Screened Porch Dining Area
Front Staircase
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
AU$5,579
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Private kitchen
Moose Lodge
Dining
Room
Exceptional
(54 reviews)

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

Great Barrington

8% off
AU$21,532
for 7 nights, 1 room
AU$3,076 per night
includes taxes & fees
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Room
Interior
Interior
Exterior
Exceptional
(44 reviews)

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

Stephentown

8% off
AU$2,471
for 7 nights, 1 home
AU$353 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Landscaped path leading to the front door.
Main living room with soaring windows overlooking the lake and wooded grounds.
Laundry room with washer, dryer, storage, and a convenient garage entry area.
Main-level queen bedroom with four-poster bed and views of the surrounding woods
Exceptional
(32 reviews)

Lake View Berkshire Retreat – Private Setting Near Lenox

Lee

15% off
AU$5,646
for 7 nights, 1 home
AU$807 per night
includes taxes & fees
Lake View Berkshire Retreat – Private Setting Near Lenox
View from Deck to Pool
Outdoor dining
Master bedroom, great view, queen size bed
Dining
Exceptional
(77 reviews)

Awesome Strategic Location Near Smith College

Williamsburg

8% off
AU$4,903
for 7 nights, 1 home
AU$700 per night
includes taxes & fees
Awesome Strategic Location Near Smith College
Outdoor spa tub
Exterior
Living area
Room
Exceptional
(22 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,576
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Dining
Interior
Exterior
Property grounds
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$9,587
for 7 nights, 1 cabin
AU$1,370 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? 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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