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Stockbridge Retreat w/ Pool & Hot Tub!

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Stockbridge Vacation Rental | 3,900 Sq Ft | 4BR | 3.5BA | Stairs Required
A covered porch with wicker furniture, large windows, and a view of a green landscape.
Living Room | Free WiFi | Central Heat & A/C | Gas Fireplace
Front Room | Piano | Books
Living area

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Heated pool
    Swim in comfort year-round in the heated pool, a rare find in this location.
  • Your private hideaway
    Guests love the secluded location for peace and quiet.
  • Discover nearby landmarks
    Walk to Housatonic River
4 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Private pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Stockbridge, MA
  • Place, Housatonic River
    ‪16 min walk‬
  • Place, Schantz Galleries
    ‪19 min walk‬
  • Place, Berkshire Theatre Festival
    ‪4 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪30 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Additional Sleeping (Den)

2 Double Sofa Beds

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Queen Bed

3 bathrooms, 1 half bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Half Bathroom

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

Stockbridge Retreat w/ Pool & Hot Tub!

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
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0437672830
Property # 9848025ha
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Glendale

Glendale is home to this vacation 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 an opportunity to explore the area for outdoor excitement like hiking.
Map
Stockbridge, MA

What's nearby

  • Housatonic River - 16 min walk - 1.4 km
  • Schantz Galleries - 19 min walk - 1.7 km
  • Mission House - 2 min drive - 1.8 km
  • Berkshire Theatre Festival - 4 min drive - 2.9 km
  • 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
  • ‪Berkshire Mountain Bakery - ‬10 min drive
  • ‪Starving Artist Creperie and Cafe - ‬10 min drive
  • ‪The Red Lion Inn - ‬17 min walk
  • ‪Fresh City - ‬16 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 Jul 14, 2026, prices found for a 1-night stay for 2 adults at Stockbridge Retreat w/ Pool & Hot Tub! on Aug 2, 2026 start from $1,699, 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?

Onsite 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!?

Check-out is at 10:00 AM.

Where is Stockbridge Retreat w/ Pool & Hot Tub! located?

Situated in Glendale, this vacation home is within 1 mi (2 km) of Schantz Galleries and Mission House. Berkshire Theatre Festival and Housatonic River are also within 2 mi (3 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 4 reviews
Rating 8 - Good. 1 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

8.8/10

Check-in

10/10

Communication

9.4/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Craig G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 14 nights in Jun 2025
From a partner site

10/10 Excellent

Max

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!
Response from VrboOwner on Jan 28, 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."
Verified

8/10 Good

Forrest R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rental Summary

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.
Stayed 5 nights in Jul 2024
Response from VrboOwner on Jan 28, 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."
Verified

10/10 Excellent

Maria L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had such a nice, relaxing visit to the Berkshires! The house is in a great location to visit lots of sights, but you could also just stay and enjoy the pool and hot tub. We loved sitting on the screened porch. There was also room for everyone to spread out inside (with multiple TVs and good WiFi) or to come together in the big family room. Our daughter enjoyed playing the piano. The kitchen is super well-equipped. There are 2 primary bedroom suites, which is very handy. The house was very clean. The host was very responsive and helpful. Only small glitch was we were given a wrong/old combination to the lockbox with the door key but that was quickly sorted out. All in all, a great place.
Stayed 7 nights in Jun 2026

About the host

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