Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soak in the hot tub, shoot some hoops, play some pickleball, or a play game of ball hockey on our private court. Or, explore nearby attractions such as the Norman Rockwell Museum, Tanglewood, and the hiking trails of the Stockbridge area.
-- THE PROPERTY --
MassTaxConnect ID #: C0437672830 | 22-Acre Property | Modern Interior | Gas Fireplace | Private Heated Pool (Depth 3.5’-9’)
Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Den: 2 Twin Futons (converts to King Bed)
OUTDOOR LIVING: Patio, private pool (open seasonally), screened-in porch, hot tub, basketball & pickleball court, gas grill, beach chairs, beach towels, deck, garden, hammock, outdoor shower, outdoor speakers, pool toys, patio heater, gas fire pit INDOOR LIVING: Board games, piano, Smart TVs, DVD player, books, ceiling fans, walk-in closet, dining table, printer KITCHEN: Air fryer, drip coffee maker, dishwasher, microwave, knife set, dishware & flatware, ice maker, spices, toaster, cooking basics GENERAL: Free WiFi, linens & towels, hair dryer, complimentary toiletries, keyless entry, washer & dryer, central heating & air conditioning FAQ: Steps required, Ring doorbell (facing out), no EV charging PARKING: Driveway (4 vehicles)
-- THE LOCATION --
OUTDOOR ADVENTURE: Monument Mountain Reservation (6 miles), Berkshire Rivers Fly Fishing (6 miles), Olivia's Overlook (8 miles), Otis Ridge (17 miles) HITTIN' SLOPES: Butternut Ski Area and Tubing Center (7 miles), Bousquet Mountain Ski Area (12 miles), Catamount Mountain Resort (14 miles), Jiminy Peak Mountain Resort (28 miles) TIME TRAVEL: Naumkeag (2 miles), Norman Rockwell Museum (3 miles), Ventfort Hall Mansion and Gilded Age Museum (7 miles), Thomas Cole National Historic Site (40 miles), Olana State Historic Site (40 miles) AIRPORTS: Albany International Airport (51 miles), Bradley International Airport (68 miles)
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - No pets allowed - No events, parties, or large gatherings - Guests are not permitted to charge electric vehicles on-site as the electrical system is not equipped for that, and the breaker will blow - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: Gardeners may be on-site in the outdoor areas, and will not disturb your stay - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Glendale
Glendale is home to this holiday home. Lee Premium Outlets and Guido's Marketplace are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Monument Mountain Reservation and Monument Mountain. Lenox Arts Center and Berkshire Botanical Garden are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking.
National Shrine of the Divine Mercy - 4 min drive - 2.9 km
Getting around
Pittsfield Intermodal Transportation Center - 24 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 23 min drive
Restaurants
McDonald's - 16 min drive
Vivaldi's Pizza - 10 min drive
51 Park Restaurant & Tavern - 10 min drive
Berkshire Mountain Bakery - 10 min drive
Starving Artist Creperie and Cafe - 10 min drive
Frequently asked questions
Does Stockbridge Retreat w/ Pool & Hot Tub! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Stockbridge Retreat w/ Pool & Hot Tub!?
As of 29 May 2026, prices found for a 1-night stay for 2 adults at Stockbridge Retreat w/ Pool & Hot Tub! on 8 Sept 2026 start from AU$2,389, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Stockbridge Retreat w/ Pool & Hot Tub! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Stockbridge Retreat w/ Pool & Hot Tub!?
On-site parking is available at the property.
What time is check-in at Stockbridge Retreat w/ Pool & Hot Tub!?
Check-in begins at 4:00 PM.
What time is check-out at Stockbridge Retreat w/ Pool & Hot Tub!?
Checkout is at 10:00 AM.
Where is Stockbridge Retreat w/ Pool & Hot Tub! located?
Situated in Glendale, this holiday home is within 1 mile (2 km) of Schantz Galleries and Mission House. Berkshire Theatre Festival and Housatonic River are also within 2 miles (3 km).
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The property was amazing. The pool, hot tub and home were excellent. The owner thought of everything you would need in the kitchen. Grill and appliances were a life saver. Owner and property manager were available for any needs and made out 2 week visit most enjoyable with no headaches.
Craig G.
Stayed 14 nights in Jun 2025
From a partner site
10/10 Excellent
Max
15 July 2024
Perfect Family Retreat in the Heart of the Berkshires
Our stay at this Stockbridge home during the July 4th week was perfect. The beautiful, secluded property provided a serene getaway, featuring a well-maintained pool area with a jacuzzi and exquisite gardening. The house is stunning, filled with natural light that makes every room feel warm and inviting. It was the perfect place for two families (with kids) to spend a week enjoying the best the Berkshires have to offer. The location was excellent, giving us easy access to all the local attractions. Plus, the house was well-stocked with plates, dishes, cookware, and everything we needed, which can be hit or miss with house rentals. We look forward to returning!
Max
Response from VrboOwner on 28 Jan 2025
From the owner: "Thank you for the kind review. We are so happy you enjoyed the home, it is a fun summer get away. We hope you visit again soon."
It is a lovely house, well equipped with games, books, piano and a beautiful swimming pool and back yard. The property manager promptly took care of a few small issues involving the lock box for key access, the garage opener code being inaccurate, and a beeping fire alarm. Although the house is on a small, quiet street, it was adjacent to a rather busy road that resulted in noise while in the backyard using the pool. There was no noise in the house however. Overall a great, well layed out home with a beautiful backyard that we enjoyed very much.
Forrest R.
Stayed 5 nights in Jul 2024
Response from VrboOwner on 28 Jan 2025
From the owner: "Thank you for your feedback, and your patience with the smoke alarm. We are happy you enjoyed our home, and hope you come back again."