Great Barrington, MA
Woodland
Sparkling Renovation, top to bottom, on quiet cul-du-sac: 5 bedrooms, 3.5 baths, sleeps 14 in beds. Max of 9 adults, preferred. Amenities: AC throughout, Spectrum internet, all new stainless appliances, wood stove (w/ wood) propane grill, umbrella and seating, fenced back yard, outdoor tether-ball, attached 2 car garage, fitness room, game room: air hockey, gaming center and convertible billiard table (ping-pong and pool). Blackout shades and all linens included! Well trained pets welcome, with pet fee. No cats, due to severe allergy. No Smoking.
Woodland offers guests a wonderful rental experience with a beautifully renovated house - everything new, privacy and quiet - tucked deep into a wooded cul-du sac, less than 10 minutes to the center of Great Barrington!
Main Floor:
Family room with large smart TV
Living room with wood stove
Open concept light-filled Kitchen and Dining
Access to Sun Deck with grill and outdoor seating
TV Den
Guest room (#5) with Queen bed
1/2 bath (powder room)
Laundry Room
Oversized 2 car garage with direct entry thru laundry
Second Floor:
Primary with King bed, floor-to-ceiling windows, blackout shades + TV lounge, walk in closet
Primary bathroom en suite with oversized shower and two shower heads!
Guest Room (#2) with Queen bed
Second bathroom with all new tiled tub/ shower
Guest room (#3) with Queen bed
Guest room (#4) with 3 Twin Beds - sleeps 6 children or 3 adults
Lower Level:
Bonus area with gaming center, billiards, ping-pong, air hockey
Fitness room
1/2 bath (sink and toilet)
Outside and Location:
Fenced back yard and very private - no road noise here!
Propane grill, sun umbrella, outdoor seating on the sun deck
Tether ball and basketball hoop
Oversized 2-car garage with direct access into the house
Location, centrally located in Great Barrington, close to all Berkshire venues! Less than 10 minutes to Guido's, 20 minutes to Tanglewood!
Close to fun eco-tourism: Taft Farm, Berkshire Mountain Bakery, Windy Hill for Apple Picking, Prairie Whale, Holli's Cafe, taco food trucks and more!
Property License: C0586351130
Sparkling Renovation, top to bottom, on quiet cul-du-sac: 5 bedrooms, 3.5 baths, sleeps 14 in beds. Max of 9 adults, preferred. Amenities: AC throughout, Spectrum internet, all new stainless appliances, wood stove (w/ wood) propane grill, umbrella and seating, fenced back yard, outdoor tether-ball, attached 2 car garage, fitness room, game room: air hockey, gaming center and convertible billiard table (ping-pong and pool). Blackout shades and all linens included! Well trained pets welcome, with pet fee. No cats, due to severe allergy. No Smoking.
Woodland offers guests a wonderful rental experience with a beautifully renovated house - everything new, privacy and quiet - tucked deep into a wooded cul-du sac, less than 10 minutes to the center of Great Barrington!
Main Floor:
Family room with large smart TV
Living room with wood stove
Open concept light-filled Kitchen and Dining
Access to Sun Deck with grill and outdoor seating
TV Den
Guest room (#5) with Queen bed
1/2 bath (powder room)
Laundry Room
Oversized 2 car garage with direct entry thru laundry
Second Floor:
Primary with King bed, floor-to-ceiling windows, blackout shades + TV lounge, walk in closet
Primary bathroom en suite with oversized shower and two shower heads!
Guest Room (#2) with Queen bed
Second bathroom with all new tiled tub/ shower
Guest room (#3) with Queen bed
Guest room (#4) with 3 Twin Beds - sleeps 6 children or 3 adults
Lower Level:
Bonus area with gaming center, billiards, ping-pong, air hockey
Fitness room
1/2 bath (sink and toilet)
Outside and Location:
Fenced back yard and very private - no road noise here!
Propane grill, sun umbrella, outdoor seating on the sun deck
Tether ball and basketball hoop
Oversized 2-car garage with direct access into the house
Location, centrally located in Great Barrington, close to all Berkshire venues! Less than 10 minutes to Guido's, 20 minutes to Tanglewood!
Close to fun eco-tourism: Taft Farm, Berkshire Mountain Bakery, Windy Hill for Apple Picking, Prairie Whale, Holli's Cafe, taco food trucks and more!
Property License: C0586351130
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Aug 21, 2026 | $571.43 | Not Available | 7 |
| Aug 22, 2026 | $571.43 | Not Available | 7 |
| Aug 23, 2026 | $571.43 | Not Available | 7 |
| Aug 24, 2026 | $571.43 | Not Available | 7 |
| Aug 25, 2026 | $571.43 | Not Available | 7 |
| Aug 26, 2026 | $571.43 | Not Available | 7 |
| Aug 27, 2026 | $571.43 | Not Available | 7 |
| Aug 28, 2026 | $571.43 | Not Available | 7 |
| Aug 29, 2026 | $571.43 | Not Available | 7 |
| Aug 30, 2026 | $571.43 | Not Available | 7 |
| Aug 31, 2026 | $571.43 | Not Available | 7 |
| Sep 1, 2026 | $571.43 | Available | 7 |
| Sep 2, 2026 | $571.43 | Available | 7 |
| Sep 3, 2026 | $571.43 | Not Available | 7 |
| Sep 4, 2026 | $571.43 | Not Available | 7 |
| Sep 5, 2026 | $571.43 | Not Available | 7 |
| Sep 6, 2026 | $571.43 | Not Available | 7 |
| Sep 7, 2026 | $700 | Available | 3 |
| Sep 8, 2026 | $700 | Available | 3 |
| Sep 9, 2026 | $700 | Available | 3 |
| Sep 10, 2026 | $700 | Available | 3 |
| Sep 11, 2026 | $700 | Not Available | 2 |
| Sep 12, 2026 | $700 | Not Available | 2 |
| Sep 13, 2026 | $700 | Available | 3 |
| Sep 14, 2026 | $700 | Available | 3 |
| Sep 15, 2026 | $700 | Available | 3 |
| Sep 16, 2026 | $700 | Available | 3 |
| Sep 17, 2026 | $700 | Not Available | 2 |
| Sep 18, 2026 | $700 | Not Available | 2 |
| Sep 19, 2026 | $700 | Not Available | 2 |
| Sep 20, 2026 | $700 | Not Available | 2 |
| Sep 21, 2026 | $700 | Available | 3 |
| Sep 22, 2026 | $700 | Available | 3 |
| Sep 23, 2026 | $700 | Available | 3 |
| Sep 24, 2026 | $700 | Not Available | 2 |
| Sep 25, 2026 | $700 | Not Available | 2 |
| Sep 26, 2026 | $700 | Not Available | 2 |
| Sep 27, 2026 | $700 | Available | 3 |
| Sep 28, 2026 | $700 | Available | 3 |
| Sep 29, 2026 | $700 | Available | 3 |
| Sep 30, 2026 | $700 | Available | 3 |
| Oct 1, 2026 | $700 | Available | 3 |
| Oct 2, 2026 | $700 | Not Available | 2 |
| Oct 3, 2026 | $700 | Not Available | 3 |
| Oct 4, 2026 | $700 | Available | 3 |
| Oct 5, 2026 | $700 | Available | 3 |
| Oct 6, 2026 | $700 | Available | 3 |
| Oct 7, 2026 | $700 | Available | 3 |
| Oct 8, 2026 | $700 | Available | 3 |
| Oct 9, 2026 | $700 | Not Available | 3 |
| Oct 10, 2026 | $700 | Not Available | 3 |
| Oct 11, 2026 | $700 | Not Available | 3 |
| Oct 12, 2026 | $700 | Available | 3 |
| Oct 13, 2026 | $700 | Available | 3 |
| Oct 14, 2026 | $700 | Available | 3 |
| Oct 15, 2026 | $700 | Not Available | 2 |
| Oct 16, 2026 | $700 | Not Available | 2 |
| Oct 17, 2026 | $700 | Not Available | 2 |
| Oct 18, 2026 | $700 | Not Available | 2 |
| Oct 19, 2026 | $700 | Available | 3 |
| Oct 20, 2026 | $700 | Available | 3 |
| Oct 21, 2026 | $700 | Available | 3 |
| Oct 22, 2026 | $700 | Available | 3 |
| Oct 23, 2026 | $700 | Available | 3 |
| Oct 24, 2026 | $700 | Available | 3 |
| Oct 25, 2026 | $650 | Available | 3 |
| Oct 26, 2026 | $650 | Available | 3 |
| Oct 27, 2026 | $650 | Available | 3 |
| Oct 28, 2026 | $650 | Available | 3 |
| Oct 29, 2026 | $650 | Available | 3 |
| Oct 30, 2026 | $650 | Available | 3 |
| Oct 31, 2026 | $650 | Available | 3 |
| Nov 1, 2026 | $650 | Not Available | 3 |
| Nov 2, 2026 | $650 | Not Available | 3 |
| Nov 3, 2026 | $650 | Not Available | 3 |
| Nov 4, 2026 | $650 | Not Available | 3 |
| Nov 5, 2026 | $650 | Not Available | 3 |
| Nov 6, 2026 | $650 | Not Available | 3 |
| Nov 7, 2026 | $650 | Not Available | 3 |
| Nov 8, 2026 | $650 | Not Available | 2 |
| Nov 9, 2026 | $650 | Not Available | 3 |
| Nov 10, 2026 | $650 | Not Available | 3 |
| Nov 11, 2026 | $650 | Not Available | 3 |
| Nov 12, 2026 | $650 | Not Available | 3 |
| Nov 13, 2026 | $650 | Not Available | 3 |
| Nov 14, 2026 | $650 | Not Available | 3 |
| Nov 15, 2026 | $650 | Not Available | 3 |
| Nov 16, 2026 | $650 | Not Available | 3 |
| Nov 17, 2026 | $650 | Not Available | 3 |
| Nov 18, 2026 | $650 | Not Available | 3 |
| Nov 19, 2026 | $650 | Not Available | 3 |
| Nov 20, 2026 | $650 | Not Available | 3 |
| Nov 21, 2026 | $650 | Available | 3 |
| Nov 22, 2026 | $700 | Available | 5 |
| Nov 23, 2026 | $700 | Available | 5 |
| Nov 24, 2026 | $700 | Available | 5 |
| Nov 25, 2026 | $700 | Available | 5 |
| Nov 26, 2026 | $700 | Available | 5 |
| Nov 27, 2026 | $700 | Available | 5 |
| Nov 28, 2026 | $700 | Available | 5 |
| Nov 29, 2026 | $650 | Not Available | 3 |
| Nov 30, 2026 | $650 | Not Available | 3 |
| Dec 1, 2026 | $650 | Not Available | 3 |
| Dec 2, 2026 | $650 | Not Available | 3 |
| Dec 3, 2026 | $650 | Not Available | 3 |
| Dec 4, 2026 | $650 | Not Available | 3 |
| Dec 5, 2026 | $650 | Not Available | 3 |
| Dec 6, 2026 | $650 | Not Available | 3 |
| Dec 7, 2026 | $650 | Not Available | 3 |
| Dec 8, 2026 | $650 | Not Available | 3 |
| Dec 9, 2026 | $650 | Not Available | 3 |
| Dec 10, 2026 | $650 | Not Available | 3 |
| Dec 11, 2026 | $650 | Not Available | 3 |
| Dec 12, 2026 | $650 | Not Available | 3 |
| Dec 13, 2026 | $650 | Not Available | 3 |
| Dec 14, 2026 | $650 | Not Available | 3 |
| Dec 15, 2026 | $650 | Not Available | 3 |
| Dec 16, 2026 | $650 | Not Available | 3 |
| Dec 17, 2026 | $650 | Not Available | 3 |
| Dec 18, 2026 | $650 | Available | 5 |
| Dec 19, 2026 | $700 | Available | 5 |
| Dec 20, 2026 | $700 | Available | 5 |
| Dec 21, 2026 | $700 | Available | 5 |
| Dec 22, 2026 | $700 | Available | 5 |
| Dec 23, 2026 | $700 | Available | 5 |
| Dec 24, 2026 | $700 | Available | 5 |
| Dec 25, 2026 | $700 | Available | 5 |
| Dec 26, 2026 | $700 | Not Available | 5 |
| Dec 27, 2026 | $700 | Not Available | 5 |
| Dec 28, 2026 | $700 | Not Available | 5 |
| Dec 29, 2026 | $700 | Not Available | 5 |
| Dec 30, 2026 | $700 | Not Available | 5 |
| Dec 31, 2026 | $700 | Not Available | 5 |
| Jan 1, 2027 | $700 | Not Available | 5 |
| Jan 2, 2027 | $700 | Available | 5 |
| Jan 3, 2027 | $700 | Not Available | 5 |
| Jan 4, 2027 | $600 | Not Available | 58 |
| Jan 5, 2027 | $600 | Not Available | 58 |
| Jan 6, 2027 | $600 | Not Available | 58 |
| Jan 7, 2027 | $600 | Not Available | 58 |
| Jan 8, 2027 | $600 | Not Available | 58 |
| Jan 9, 2027 | $600 | Not Available | 58 |
| Jan 10, 2027 | $600 | Not Available | 58 |
| Jan 11, 2027 | $600 | Not Available | 58 |
| Jan 12, 2027 | $600 | Not Available | 58 |
| Jan 13, 2027 | $600 | Not Available | 58 |
| Jan 14, 2027 | $600 | Not Available | 58 |
| Jan 15, 2027 | $600 | Not Available | 58 |
| Jan 16, 2027 | $600 | Not Available | 58 |
| Jan 17, 2027 | $600 | Not Available | 58 |
| Jan 18, 2027 | $600 | Not Available | 58 |
| Jan 19, 2027 | $600 | Not Available | 58 |
| Jan 20, 2027 | $600 | Not Available | 58 |
| Jan 21, 2027 | $600 | Not Available | 58 |
| Jan 22, 2027 | $600 | Not Available | 58 |
| Jan 23, 2027 | $600 | Not Available | 58 |
| Jan 24, 2027 | $600 | Not Available | 58 |
| Jan 25, 2027 | $600 | Not Available | 58 |
| Jan 26, 2027 | $600 | Not Available | 58 |
| Jan 27, 2027 | $600 | Not Available | 58 |
| Jan 28, 2027 | $600 | Not Available | 58 |
| Jan 29, 2027 | $600 | Not Available | 58 |
| Jan 30, 2027 | $600 | Not Available | 58 |
| Jan 31, 2027 | $600 | Not Available | 58 |
| Feb 1, 2027 | $600 | Not Available | 58 |
| Feb 2, 2027 | $600 | Not Available | 58 |
| Feb 3, 2027 | $600 | Not Available | 58 |
| Feb 4, 2027 | $600 | Not Available | 58 |
| Feb 5, 2027 | $600 | Not Available | 58 |
| Feb 6, 2027 | $600 | Not Available | 58 |
| Feb 7, 2027 | $600 | Not Available | 58 |
| Feb 8, 2027 | $600 | Not Available | 58 |
| Feb 9, 2027 | $600 | Not Available | 58 |
| Feb 10, 2027 | $600 | Not Available | 58 |
| Feb 11, 2027 | $600 | Not Available | 58 |
| Feb 12, 2027 | $600 | Not Available | 58 |
| Feb 13, 2027 | $600 | Not Available | 58 |
| Feb 14, 2027 | $600 | Not Available | 58 |
| Feb 15, 2027 | $600 | Not Available | 58 |
| Feb 16, 2027 | $600 | Not Available | 58 |
| Feb 17, 2027 | $600 | Not Available | 58 |
| Feb 18, 2027 | $600 | Not Available | 58 |
| Feb 19, 2027 | $600 | Not Available | 58 |
| Feb 20, 2027 | $600 | Not Available | 58 |
| Feb 21, 2027 | $600 | Not Available | 58 |
| Feb 22, 2027 | $600 | Not Available | 58 |
| Feb 23, 2027 | $600 | Not Available | 58 |
| Feb 24, 2027 | $600 | Not Available | 58 |
| Feb 25, 2027 | $600 | Not Available | 58 |
| Feb 26, 2027 | $600 | Not Available | 58 |
| Feb 27, 2027 | $600 | Not Available | 58 |
| Feb 28, 2027 | $600 | Not Available | 58 |
| Mar 1, 2027 | $600 | Not Available | 58 |
| Mar 2, 2027 | $600 | Not Available | 58 |
| Mar 3, 2027 | $600 | Not Available | 58 |
| Mar 4, 2027 | $600 | Not Available | 58 |
| Mar 5, 2027 | $600 | Not Available | 58 |
| Mar 6, 2027 | $600 | Not Available | 58 |
| Mar 7, 2027 | $600 | Not Available | 58 |
| Mar 8, 2027 | $600 | Not Available | 58 |
| Mar 9, 2027 | $600 | Not Available | 58 |
| Mar 10, 2027 | $600 | Not Available | 58 |
| Mar 11, 2027 | $600 | Not Available | 58 |
| Mar 12, 2027 | $600 | Not Available | 58 |
| Mar 13, 2027 | $600 | Not Available | 58 |
| Mar 14, 2027 | $550 | Not Available | 2 |
| Mar 15, 2027 | $550 | Not Available | 3 |
| Mar 16, 2027 | $550 | Not Available | 3 |
| Mar 17, 2027 | $550 | Not Available | 3 |
| Mar 18, 2027 | $550 | Not Available | 3 |
| Mar 19, 2027 | $550 | Not Available | 3 |
| Mar 20, 2027 | $550 | Not Available | 3 |
| Mar 21, 2027 | $550 | Not Available | 3 |
| Mar 22, 2027 | $550 | Not Available | 3 |
| Mar 23, 2027 | $550 | Not Available | 3 |
| Mar 24, 2027 | $550 | Not Available | 3 |
| Mar 25, 2027 | $550 | Not Available | 3 |
| Mar 26, 2027 | $550 | Not Available | 3 |
| Mar 27, 2027 | $550 | Not Available | 3 |
| Mar 28, 2027 | $550 | Not Available | 3 |
| Mar 29, 2027 | $550 | Not Available | 3 |
| Mar 30, 2027 | $550 | Not Available | 3 |
| Mar 31, 2027 | $550 | Not Available | 3 |
| Apr 1, 2027 | $550 | Not Available | 3 |
| Apr 2, 2027 | $550 | Not Available | 3 |
| Apr 3, 2027 | $550 | Not Available | 3 |
| Apr 4, 2027 | $550 | Not Available | 3 |
| Apr 5, 2027 | $550 | Not Available | 3 |
| Apr 6, 2027 | $550 | Not Available | 3 |
| Apr 7, 2027 | $550 | Not Available | 3 |
| Apr 8, 2027 | $550 | Not Available | 3 |
| Apr 9, 2027 | $550 | Not Available | 3 |
| Apr 10, 2027 | $550 | Not Available | 3 |
| Apr 11, 2027 | $550 | Not Available | 3 |
| Apr 12, 2027 | $550 | Not Available | 3 |
| Apr 13, 2027 | $550 | Not Available | 3 |
| Apr 14, 2027 | $550 | Not Available | 3 |
| Apr 15, 2027 | $550 | Not Available | 3 |
| Apr 16, 2027 | $550 | Not Available | 3 |
| Apr 17, 2027 | $550 | Not Available | 3 |
| Apr 18, 2027 | $550 | Not Available | 3 |
| Apr 19, 2027 | $550 | Not Available | 3 |
| Apr 20, 2027 | $550 | Not Available | 3 |
| Apr 21, 2027 | $550 | Not Available | 3 |
| Apr 22, 2027 | $550 | Not Available | 2 |
| Apr 23, 2027 | $550 | Not Available | 2 |
| Apr 24, 2027 | $550 | Not Available | 2 |
| Apr 25, 2027 | $550 | Not Available | 3 |
| Apr 26, 2027 | $550 | Not Available | 3 |
| Apr 27, 2027 | $550 | Not Available | 3 |
| Apr 28, 2027 | $550 | Not Available | 33 |
| Apr 29, 2027 | $550 | Not Available | 3 |
| Apr 30, 2027 | $550 | Not Available | 3 |
| May 1, 2027 | $550 | Not Available | 3 |
| May 2, 2027 | $550 | Not Available | 3 |
| May 3, 2027 | $550 | Not Available | 3 |
| May 4, 2027 | $550 | Not Available | 3 |
| May 5, 2027 | $550 | Not Available | 3 |
| May 6, 2027 | $550 | Not Available | 3 |
| May 7, 2027 | $550 | Not Available | 3 |
| May 8, 2027 | $550 | Not Available | 3 |
| May 9, 2027 | $550 | Not Available | 3 |
| May 10, 2027 | $550 | Not Available | 3 |
| May 11, 2027 | $550 | Not Available | 3 |
| May 12, 2027 | $550 | Not Available | 3 |
| May 13, 2027 | $550 | Not Available | 3 |
What this home offers
Where you’ll be
Great Barrington, MA, 01230, US
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You’ll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We’re building a relationship, not closing a booking.
Things to know
Check-in & check-out
Check-in after 3:00 PM.
Check-out before 11:00 AM.
Property rules
Children welcome (2–12 years).
Infants welcome (under 2).
Maximum 14 guests.
Pets allowed.
No parties or events.
Number and age of guests
Pets
Events
Smoking
Check-in & check-out
Cancellation policy
Contact us for cancellation policy details prior to booking.