Photo by Caitlin Reese

Holiday rentals near Monument Mountain Reservation

We found 473 holiday rentals — enter your dates for availability

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November 2025

December 2025

Find the perfect private holiday rental within easy reach of Monument Mountain Reservation. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Monument Mountain Reservation

Showing deals for:6 Feb - 13 Feb

Exceptional

(27 reviews)

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington, MA

8% off

for 7 nights, 1 home

AU$1,312 per night

includes taxes & fees

Exceptional

(7 reviews)

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge, MA

8% off

for 7 nights, 1 room

AU$1,874 per night

includes taxes & fees

Exceptional

(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington, MA

8% off

for 7 nights, 1 cottage

AU$552 per night

includes taxes & fees

Exceptional

(9 reviews)

Cozy retreat in beautiful country setting

Lee, MA

8% off

for 7 nights, 1 apartment

AU$536 per night

includes taxes & fees

Exceptional

(110 reviews)

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA

8% off

for 7 nights, 1 home

AU$2,043 per night

includes taxes & fees

Wonderful

(32 reviews)

Amore Estate - beautiful room with many places to explore and relax in.

Lenox, MA

8% off

for 7 nights, 1 home

AU$1,637 per night

includes taxes & fees

Ultimate Relaxation! The hot tub will be warm and waiting for your arrival

Exceptional

(7 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, MA

11% off

for 7 nights, 1 home

AU$694 per night

includes taxes & fees

Exceptional

(43 reviews)

Jaw dropping mountain & lake views in this stylish mountain home….

Monterey, MA

8% off

for 7 nights, 1 home

AU$1,189 per night

includes taxes & fees

Recharge with family and friends, this relaxing lounging area features leather couch that seats up to 10-12, a gas fireplace, and a 65 inch UHD smart TV.

Exceptional

(45 reviews)

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, MA

16% off

for 7 nights, 1 home

AU$855 per night

includes taxes & fees

Amazing views from your private city escape.

Wonderful

(7 reviews)

Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!

Austerlitz, NY

8% off

for 7 nights, 1 cabin

AU$1,295 per night

includes taxes & fees

Exceptional

(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox, MA

11% off

for 7 nights, 1 home

AU$825 per night

includes taxes & fees

You will love dining and working in this rich and colorful room

Exceptional

(29 reviews)

An In-Town Beauty with Late Checkout

Great Barrington, MA

11% off

for 7 nights, 1 home

AU$675 per night

includes taxes & fees

Exceptional

(28 reviews)

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Great Barrington, MA

7% off

for 7 nights, 1 home

AU$1,093 per night

includes taxes & fees

Exceptional

(49 reviews)

Berkshire Mountain Cottage: in the Heart of the Berkshires

Great Barrington, MA

5% off

for 7 nights, 1 cottage

AU$419 per night

includes taxes & fees

Exceptional

(30 reviews)

Stockbridge Home, Come Experience The Berkshires!

Glendale, MA

14% off

for 7 nights, 1 home

AU$656 per night

includes taxes & fees

Exceptional

(7 reviews)

Catamount, Zip Line, Private Setting, Book Now!

Great Barrington, MA

7% off

for 7 nights, 1 home

AU$758 per night

includes taxes & fees

Cozy living room nestled between the oversized kitchen and four-season porch.

Exceptional

(10 reviews)

4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee

Lee, MA

8% off

for 7 nights, 1 home

AU$555 per night

includes taxes & fees

Exceptional

(62 reviews)

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

Lenox, MA

8% off

for 7 nights, 1 home

AU$902 per night

includes taxes & fees

Find spaces that suit your style

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Find properties near top attractions in Monument Mountain Reservation

Monument Mountain Reservation

Find the best place to stay - Monument Mountain Reservation

Showing deals for: 31 Jan - 3 Feb

The Ponds at Foxhollow

Sleeps 4 · 1 bedroom

for 3 nights, 1 apartment

AU$248 per night

includes taxes & fees

Premier Host

Great Barrington, Cabin Sleeps 14, Walk To Town

Sleeps 14 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 home

AU$1,058 per night

includes taxes & fees

Premier Host

Amore Estate - beautiful room with many places to explore and relax in.

Sleeps 12 · 6 bedrooms · 4 bathrooms

for 3 nights, 1 home

AU$1,884 per night

includes taxes & fees

Breakfast Nook - wake up to the best sunshine ever!

Premier Host

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Sleeps 8 · 4 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$781 per night

includes taxes & fees

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Enjoy full kitchens, laundry, pools, gardens and more
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