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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Browse Select Pittsfield Holiday Homes

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

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

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
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, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (55)
"Margarete and Alice welcomed us upon arrival. The house was the quintessential New England home! It was super clean, our bed was very comfortable with soft welcoming linens. The views are incredible, and the property provided much needed peace and tranquility. The weather was not the best but we managed to find plenty to do in the area. Alice, Margarete's black lab, took us for a hike on the property. She was an excellent playful guide! We look forward to returning to this peaceful retreat in...
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Property grounds

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is £119
includes taxes & fees
24 Aug - 25 Aug
104 Two Queen Bed Standard Hotel Room outdoor heated pool
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, (16)
"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
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Smart TV, fireplace

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
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
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, (109)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Exterior

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (220)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
BRIDGEWATER RETREAT
Exterior

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (7)
"A true gem."
BRIDGEWATER RETREAT
The Brandon Inn - Fourth Floor Queen Room
Exterior

The Brandon Inn - Fourth Floor Queen Room

8.8 out of 10, Excellent, (6)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is £143
includes taxes & fees
24 Aug - 25 Aug
The Brandon Inn - Fourth Floor Queen Room
Deluxe One bedroom Queen Suite with outdoor heated pool 203
Fridge, microwave, oven, stovetop

Deluxe One bedroom Queen Suite with outdoor heated pool 203

9.4 out of 10, Exceptional, (9)
"Condo was clean & well furnished. Only stayed one night after a visit to Quechee, Woodstock, and area."
The price is £129
includes taxes & fees
24 Aug - 25 Aug
Deluxe One bedroom Queen Suite with outdoor heated pool 203
Recently updated home with shared hot tub, pool, and easy ski access
Indoor pool

Recently updated home with shared hot tub, pool, and easy ski access

8.4 out of 10, Very good, (44)
"Great place"
Recently updated home with shared hot tub, pool, and easy ski access
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (10)
"We loved the community space and how the layout was conducive to comfort and space to gather together.Bonus to have so many bathrooms! The windows and light were spectacular!"
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
New Listing - Luxury log home with stunning views
Interior

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"Beautiful house on an amazing piece of property. The house was very comfortable for two families of four. It has everything you could need and more. The hosts were very responsive. We will definitely stay here again."
New Listing - Luxury log home with stunning views
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Dining

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
The price is £462
includes taxes & fees
26 Aug - 27 Aug
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Valley View Retreat is a tastefully decorated home. Beautiful views
TV, fireplace

Valley View Retreat is a tastefully decorated home. Beautiful views

10.0 out of 10, Exceptional, (2)
"The home was so comfortable and had a gorgeous view of the mountains. It was so convenient to the ski slopes. Our family of 4 really enjoyed our stay."
Valley View Retreat is a tastefully decorated home. Beautiful views
Killington ski house
Fridge, microwave, oven, stovetop

Killington ski house

9.4 out of 10, Exceptional, (35)
"Property owner was excellent! We enjoyed our stay."
Killington ski house
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!
Fridge, microwave, stovetop, dishwasher

Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!

7.0 out of 10, Good, (2)
"This rental was not only clean and roomy but in a great spot. It was spacious throughout and the beds were comfortable. The backyard and hot tub were very nice too.. I would definitely stay again!"
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is £72
includes taxes & fees
24 Aug - 25 Aug
Off Grid Glamping Shed with River Access
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts."
mark 2-night trip
Posted 1 day ago
North Star Lodge and Resort