Pittsfield Vacation Rentals

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Browse Select Pittsfield Vacation Homes

Killington Farmhouse-Mountain Biking, Golf, Hiking

10.0 out of 10, Exceptional, (3)
"We visited in the summer…Spacious with room to spread out. Clean with all the things you need. Good communication. Laundry area a little spooky but great working laundry area."
Killington Farmhouse-Mountain Biking, Golf, Hiking

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

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

10.0 out of 10, Exceptional, (58)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

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

8.4 out of 10, Very good, (42)
"Great place"
Recently updated home with shared hot tub, pool, and easy ski access

Premier Woodstock Village Riverfront Home

Premier Woodstock Village Riverfront Home

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

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
The price is CA $137
CA $434 total
includes taxes & fees
Aug 10 - Aug 11
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

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

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

9.8 out of 10, Exceptional, (218)
"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.

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

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

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

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Historic Charm, Located On the River - Rustic Chic

10.0 out of 10, Exceptional, (1)
"Amazing location and great house!! "
Historic Charm, Located On the River - Rustic Chic

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 CA $143
CA $216 total
includes taxes & fees
Aug 10 - Aug 11
104 Two Queen Bed Standard Hotel Room outdoor heated pool

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is CA $209
CA $290 total
includes taxes & fees
Aug 11 - Aug 12
Sleep Woodstock - 2 Double Beds - Dog Friendly

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

9.2 out of 10, Wonderful, (37)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

9.8 out of 10, Exceptional, (46)
"Couldn’t ask for much more than this property. Perfect location near Sugar Bush, big beautiful hot tub and wood fireplace to relax by at the end of the night. Blend that with a huge kitchen to cook in and basement / rec room for the kids to call their own and it created an environment for the perfect week. Great location, great communication all around. "
Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont

The price is CA $227
CA $700 total
includes taxes & fees
Aug 10 - Aug 11
The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont

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

10.0 out of 10, Exceptional, (8)
"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

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 CA $272
CA $833 total
includes taxes & fees
Aug 11 - Aug 12
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

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
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