Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Holiday Homes in Pittsfield and around

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, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Exterior

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

10.0 out of 10, Exceptional, (110)
"Clean and great location!"
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Ski house 8 min from the mountain
Fridge, microwave, oven, stovetop

Ski house 8 min from the mountain

9.6 out of 10, Exceptional, (20)
"House was cozy, had great facilities, the location was perfect and the owner was very responsive to any questions. Definitely would visit again. "
Ski house 8 min from the mountain
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, (28)
"The host and house manager are absolutely the best. Felt very taken care of - they went above and beyond."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
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, (26)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
New Listing - Luxury log home with stunning views
Interior

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"We had a great time enjoying this beautiful home!! Great for family getaways!!"
New Listing - Luxury log home with stunning views
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Terrace/patio

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (77)
"The feel was so relaxing, felt like home.Im at a loss for words was just wonderful."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Perfect Woodstock Getaway! Lovely Riverside Home
Fridge, microwave, oven, stovetop

Perfect Woodstock Getaway! Lovely Riverside Home

9.8 out of 10, Exceptional, (8)
"We had a wonderful weekend at Charlie's house. The property was clean and welcoming and the fenced in backyard was excellent for our dog Riley"
Perfect Woodstock Getaway! Lovely Riverside Home
BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater
Fridge, microwave, oven, stovetop

BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

10.0 out of 10, Exceptional, (1)
"This place is amazing! Great location. Very smooth check in and check out . Good communication with owners. Very clean and new! "
BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater
Charming Ranch in the Woods - Woodstock Way
Fridge, microwave, oven, stovetop

Charming Ranch in the Woods - Woodstock Way

8.0 out of 10, Very good, (2)
"This was the perfect place to celebrate our 20th wedding anniversary. Woodstock was a place we frequented throughout our dating years and our marriage. This home was close to town but private. It was absolutely beautiful inside and easy to get to. The owners were communicative from the moment we booked and responded promptly with any questions. It was so easy. We were able to go into town, and come back and relax at the house. It was absolutely perfect. It was as advertised as well. There...
Charming Ranch in the Woods - Woodstock Way
Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12
Games room

Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12

10.0 out of 10, Exceptional, (29)
"Wonderful weekend with friends. 10 minute drive to lifts and close to a few restaurants. Plenty of space at the house to spread out and relax"
Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
Dining

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

10.0 out of 10, Exceptional, (84)
"It's a grand old house and the property is beautiful."
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Fridge, microwave, oven, stovetop

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (66)
"The perfect place for our friends and family to stay!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Interior

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

9.6 out of 10, Exceptional, (57)
"Cute house nestled in the woods, great location and private hot tub on the deck! We enjoyed every second of it!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
BRIDGEWATER RETREAT
Exterior

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (9)
"A true gem."
BRIDGEWATER RETREAT
3BR w Incredible View, Hot Tub & Sauna
Property grounds

3BR w Incredible View, Hot Tub & Sauna

10.0 out of 10, Exceptional, (6)
"Very nice unit. Plenty of space, and great views of the mountain. "
3BR w Incredible View, Hot Tub & Sauna
Luxury Condo Tucked in the Heart of Killington
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

The price is €267
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo Tucked in the Heart of Killington
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, (18)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
Cheerful 3 bed/2.5 bath home w/ hot tub - sleeps 9
Exterior

Cheerful 3 bed/2.5 bath home w/ hot tub - sleeps 9

9.6 out of 10, Exceptional, (4)
"Super cute home at the end of a short dirt road."
Cheerful 3 bed/2.5 bath home w/ hot tub - sleeps 9
RoundTop Chalet- Hot Tub, Grill, Hiking!
Outdoor spa tub

RoundTop Chalet- Hot Tub, Grill, Hiking!

10.0 out of 10, Exceptional, (2)
"Wonderful Stay! Very helpful and quick to respond to any questions. Several small towns around Plymouth to enjoy."
RoundTop Chalet- Hot Tub, Grill, Hiking!
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river. "
Natalie 1-night trip
Posted 3 days ago
The Shire Woodstock

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
487
Accommodation
658 Holiday Homes
Lowest Price
€267
Highest Price
€267

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