Cottages in Pittsfield

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Populaire Cottages in Pittsfield

The Clearing - Quiet - Close To Nature

10.0 van 10, Uitzonderlijk, (195)
'Everything was great: kitchen, WiFI, etc.'
The Clearing - Quiet - Close To Nature

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0-sterrenaccommodatie
9.0 van 10, Fantastisch, (4)
'Beautiful cabin in beautiful setting. Cabin was well furnished, had well stocked kitchen, and modern amenities. There were lots of attractions within 30 minute, scenic drives from the cabin such as Tanglewood, Monument Mountain, and other Berkshire and Columbia County attractions. Avid cyclists will find smooth roads with good shoulders and light traffic. As noted n another review, there is a rail line about one mile from the cabin, thus inevitable noise on occasion. It was well worth the trade...
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 van 10, Uitzonderlijk, (85)
'A wonderful pet- friendly rental! We drove from NC to stay on the lake and were very happy with this cute little cottage. Comfortable inside with great views outside. Overall a great space for entertaining family and friends or just chilling out for a bit. And our lab enjoyed herself too!'
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 van 10, Fantastisch, (7)
'From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 van 10, Uitzonderlijk, (11)
'Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. '
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 van 10, Fantastisch, (40)
'This is an adorable, rustic lakeside cabin n the Berks, it’s the real deal and very comfortable and simply but well appointed. We felt like part of the multi-generational family history in the quaint camp. The lake is beautiful and smaller, so peaceful, definitely grab some firewood along the road for the fire pit. We had a wonderful relaxing lakeside holiday. '
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Charming historic cottage on scenic road to Mt. Greylock

10.0 van 10, Uitzonderlijk, (113)
'The schoolhouse was adorable. Very comfortable and clean. Decorated with so many interesting books and antiques. '
Charming historic cottage on scenic road to Mt. Greylock

Entire cottage in Berkshire Villiage

3.0-sterrenaccommodatie
9.6 van 10, Uitzonderlijk, (5)
'This was such a cute and comfortable cottage! We had a lovely stay here and even though it was in a woodsy setting, we appreciated that it was just minutes away from a Target and big grocery store. Convenient for emergency shopping. '
Entire cottage in Berkshire Villiage

Beachwood Cottage

9.6 van 10, Uitzonderlijk, (5)
'We were lucky enough to find the Cottage right before July 4. Our son and his wife's whole extended family were spending the weekend in the same Beachwood neighborhood. The immediate area is fabulous for a low-key, family-oriented weekend. The cottage has been updated with room airconditioners and heat, a cooktop, fridge, etc. That said, it's a cottage and not a hotel. Although we did do a bit of cooking there, it would be hard to cook a full meal with any frequency. Still, we really had...
Beachwood Cottage

Quiet rustic cottage with shared lake access

10.0 van 10, Uitzonderlijk, (109)
'We had a family wedding being held at Gedney Farmers 20 minutes away and it was the perfect location! Hotels near the venue were full and this home saved the day! Booking was easy and communication was efficient. Thank you so much for sharing your beautiful home. '
Quiet rustic cottage with shared lake access

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 van 10, Uitzonderlijk, (13)
'Lovely cottage. Great for 2 couples. Lots of privacy for each but comfy gathering spots for dining and relaxing. Host was very responsive to questions. Great stay!'
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Cozy cottage with pool, walking distance to lake

10.0 van 10, Uitzonderlijk, (15)
'This was our third year in a row staying here! Booking a fourth stay for 2026! We especially love the pool! The house is clean and comfortable and it's a great spot for a long weekend for us.Great communication with the owner.'
Cozy cottage with pool, walking distance to lake

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake

Lake Views & Dock Access - Pittsfield Cottage!

10.0 van 10, Uitzonderlijk, (4)
'We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood.'
Lake Views & Dock Access - Pittsfield Cottage!

Charlemont Retreat on Chickley River w/ EV Charger

3.0-sterrenaccommodatie
10.0 van 10, Uitzonderlijk, (1)
'Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 van 10, Uitzonderlijk, (6)
'Great quiet stay near the lake - easy access to our many Berkshires destinations '
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Luxury Vacation Rental in the Berkshires!

3.0-sterrenaccommodatie
Luxury Vacation Rental in the Berkshires!

Berkshires farm, 30+ guests, 50 acres

2.0-sterrenaccommodatie
De prijs is € 1.481
inclusief belastingen en toeslagen
9 sep - 10 sep
Berkshires farm, 30+ guests, 50 acres

A-frame Cabin w/ Furnished Deck in Becket!

3.0-sterrenaccommodatie
A-frame Cabin w/ Furnished Deck in Becket!

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0-sterrenaccommodatie
Private Hot Tub: Hudson Valley Cabin Retreat!
Laagste prijs per nacht gevonden in de afgelopen 24 uur op basis van een verblijf van 1 nacht voor 2 volwassenen. Prijzen en beschikbaarheid kunnen wijzigen. Mogelijk gelden er extra voorwaarden.
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