Fall Season in Western Massachusetts

Western Massachusetts Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Western Massachusetts holiday rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,406 reviews)
"Property is great and stay was great"
United States
Isha
The price is HK$932
HK$1,127 total
includes taxes & fees
16 Jul - 17 Jul
Vacation Village in the Berkshires
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$903
HK$1,008 total
includes taxes & fees
24 Jun - 25 Jun
Huttopia Berkshires
Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is HK$768
HK$2,116 total
includes taxes & fees
28 Jun - 29 Jun
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is HK$966
HK$1,640 total
includes taxes & fees
6 Jul - 7 Jul
Lovely 2nd Floor Apartment
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is HK$940
HK$2,221 total
includes taxes & fees
24 Jun - 25 Jun
2-Bdr Apt In Town, By the Water
Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"We had a great"
United States
Meredith B.
The price is HK$741
HK$1,904 total
includes taxes & fees
24 Jun - 25 Jun
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$964
HK$2,195 total
includes taxes & fees
29 Jun - 30 Jun
Downtown | Waterfront | Walk to Shops
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is HK$854
HK$1,069 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$910
HK$1,953 total
includes taxes & fees
23 Jun - 24 Jun
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is HK$1,023
HK$1,484 total
includes taxes & fees
23 Jun - 24 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
1 bedroom, desk, iron/ironing board, travel cot

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is HK$1,411
HK$2,197 total
includes taxes & fees
23 Jun - 24 Jun
The Creation Station is a cozy place so make yourself at home.
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is HK$635
HK$1,462 total
includes taxes & fees
23 Jun - 24 Jun
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Pool

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"Host very responsive. I gave feedback that could make stay better like more hangars and some coat hooks. Massage chair in unit was a hit with the whole family.Unit is literally the last unit in last builing of Coubtry Inn away from ski school and Express lift. Still walkable, just not in ski boots.Parking in front of unit super easy.No elevator nearby. Upstairs with luggage. "
United States
Joe C.
The price is HK$1,552
HK$2,758 total
includes taxes & fees
28 Jun - 29 Jun
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Gift shop

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$910
HK$1,953 total
includes taxes & fees
23 Jun - 24 Jun
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (30 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is HK$1,234
HK$1,678 total
includes taxes & fees
24 Jun - 25 Jun
Newly Built Barn Loft in Pioneer Valley
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is HK$952
HK$1,414 total
includes taxes & fees
23 Jun - 24 Jun
comfort, luxury, privacy
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is HK$952
HK$2,009 total
includes taxes & fees
23 Jun - 24 Jun
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (13 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$980
HK$2,168 total
includes taxes & fees
29 Jun - 30 Jun
New Studio In Town, By the Water
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,143
HK$2,913 total
includes taxes & fees
23 Jun - 24 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (2 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is HK$690
HK$2,135 total
includes taxes & fees
28 Jun - 29 Jun
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Western Massachusetts Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"I was so happy with our stay! Everyone was so helpful and nice. The hotel is new and beautiful. I didn’t want to leave!!"
Terri L 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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