Search Vacation Homes in Pittsfield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 626 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (22)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Miscellaneous

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

10.0 out of 10, Exceptional, (3)
"The property was perfect for a Vermont getaway that will allow you to enjoy the autumn views and still give you the opportunity to engage in plenty of activities if you desire. Highly recommend this home!!"
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Cozy Private Bedroom with Own Entrance - No Shower
1 bedroom, free WiFi, bed sheets

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"Very comfortable stay. "
The price is AED 294
AED 448 total
includes taxes & fees
11 May - 12 May
Cozy Private Bedroom with Own Entrance - No Shower
Spacious country home, beautiful sunsets, 40 acres
Exterior

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"Awsome place to stay for a week! "
The price is AED 569
AED 1,880 total
includes taxes & fees
14 May - 15 May
Spacious country home, beautiful sunsets, 40 acres
Classic Vermont Farmhouse near Sugarbush Resort
Property grounds

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (36)
"A perfect location for family weekend at Norwich University! We fit a family of 7 and all slept comfortably, lounged in the living room, or gathered in the spacious kitchen where I cooked and baked all weekend. We will definitely stay again!"
Classic Vermont Farmhouse near Sugarbush Resort
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property map

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (36)
"Great location for ski in/out. Ideal for a small family "
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
TV, fireplace

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (3)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Exterior

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Fridge, microwave, oven, stovetop

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
11 May - 12 May
Off Grid Glamping Shed with River Access
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Outdoor dining

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Perfect location between okemo and Killington. House was great with awesome views."
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Smart TV, fireplace, books

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (32)
"We enjoyed our stay and the house"
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Outdoor dining

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.4 out of 10, Very Good, (26)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.4 out of 10, Exceptional, (120)
"Great stay"
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Spectacular 4 Bed Killington Home
Exterior

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (118)
"Beautiful location"
Spectacular 4 Bed Killington Home
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
Fridge, microwave, stovetop, dishwasher

Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.

9.8 out of 10, Exceptional, (53)
"Very much enjoyed our stay at the Sunburst home. Had great amenities, the host was communicative, & the location was perfect. Would stay again!"
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
Lake

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (82)
"This the most lobvely farmhouse, with everything in it of great taste, comfort and stunning views and grounds to explore. Who can ask for more?"
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
FiddleHead Lane-Near Killington, Fireplace, Grill
Fridge, microwave, oven, stovetop

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"My family of 8 stayed here for a ski vacation, and we loved it. Everything from the comfy beds, well equipped kitchen, space for ski equipment, and room for all of us to be together was perfect!! The hosts were Amazing! "
The price is AED 463
AED 2,114 total
includes taxes & fees
11 May - 12 May
FiddleHead Lane-Near Killington, Fireplace, Grill
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
Terrace/patio

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (14)
"The owners were wonderful and very responsive. We enjoyed our stay - beautiful location and view. The home was extremely inviting and perfect for our needs! "
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+
Private Killington Area Inn all to Yourself!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Overall fabulous place to stay. Will be back next year!!"
Private Killington Area Inn all to Yourself!
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.