Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Pittsfield holiday rentals

Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,462
HK$4,308 total
includes taxes & fees
21 Jun - 22 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (20 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is HK$4,929
HK$9,005 total
includes taxes & fees
23 Jun - 24 Jun
Hancock Village Inn Near Jiminy Peak
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$903
HK$1,008 total
includes taxes & fees
21 Jun - 22 Jun
Huttopia Berkshires
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is HK$1,567
HK$2,634 total
includes taxes & fees
21 Jun - 22 Jun
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
BLUSH: Boutique TINY home*private spa*walk to town
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,400 reviews)
"Property is great and stay was great"
United States
Isha
The price is HK$932
HK$1,127 total
includes taxes & fees
16 Jul - 17 Jul
Vacation Village in the Berkshires
1 bedroom, free WiFi, bed sheets

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$1,097
HK$1,566 total
includes taxes & fees
25 Jun - 26 Jun
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,636
HK$3,570 total
includes taxes & fees
30 Jun - 1 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is HK$1,803
HK$2,976 total
includes taxes & fees
21 Jun - 22 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,500
HK$4,912 total
includes taxes & fees
22 Jun - 23 Jun
Treetop Hideaway in Tyringham
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is HK$2,665
HK$4,968 total
includes taxes & fees
19 Jul - 20 Jul
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is HK$846
HK$1,060 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is HK$940
HK$2,221 total
includes taxes & fees
21 Jun - 22 Jun
2-Bdr Apt In Town, By the Water
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is HK$979
HK$1,435 total
includes taxes & fees
27 Jun - 28 Jun
Taborton Harvest Boulder Pines Cabin in the woods
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$980
HK$2,041 total
includes taxes & fees
21 Jun - 22 Jun
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$964
HK$2,195 total
includes taxes & fees
30 Jun - 1 Jul
Downtown | Waterfront | Walk to Shops
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$776
HK$2,705 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is HK$635
HK$1,462 total
includes taxes & fees
22 Jun - 23 Jun
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is HK$910
HK$1,598 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Home in Pownal VT
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is HK$980
HK$2,041 total
includes taxes & fees
21 Jun - 22 Jun
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet."
Kyra 2-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
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  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Pittsfield is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an electric kettle, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Pittsfield?

With 38 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 Berkshire Athenaeum and Colonial Theater.

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.