Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is NZ$1,768
includes taxes & fees
20 Aug - 21 Aug
Hancock Village Inn at Jiminy Peak

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (123)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (58)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1947)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is NZ$221
includes taxes & fees
28 Aug - 29 Aug
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (962)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is NZ$300
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is NZ$183
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (125)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is NZ$319
includes taxes & fees
16 Aug - 17 Aug
Taborton Harvest Boulder Pines Cabin in the woods

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,321
includes taxes & fees
21 Aug - 22 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is NZ$316
includes taxes & fees
16 Aug - 17 Aug
Taborton Harvest Timber Trails Unique cabin experience

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

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

9.8 out of 10, Exceptional, (85)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (4)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is NZ$222
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (88)
"Our group had a great time. The place is a bit dated but has room for plenty of people."
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (195)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
The price is NZ$1,002
includes taxes & fees
19 Aug - 20 Aug
Bear Creek Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals in Pittsfield close to Berkshire Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

What are some of the best holiday rentals that Pittsfield has to offer?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This highly rated holiday home rental in Pittsfield is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate Hancock Village Inn at Jiminy Peak as a favourite home for rent in Pittsfield.

How many holiday rentals are there in Pittsfield?

With 39 Expedia holiday rentals, you're guaranteed to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Barrington Stage Company.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.