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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 35 Cottages in Pittsfield with updated reviews, rates, and availability.

Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
Property grounds

Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock

9.8 out of 10, Exceptional, (10)
"Cottage was very clean and stocked with basic essentials. Owner was very responsive to our texts and communicated well. Great view of lake from cabin. We had a wonderful stay and hope to go back some day."
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (52)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is SAR 469
SAR 735 total
includes taxes & fees
16 Mar - 17 Mar
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
1 bedroom, free WiFi, bed sheets

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (90)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House
New Lakeside Cottage near Okemo and Killington

New Lakeside Cottage near Okemo and Killington

9.6 out of 10, Exceptional, (153)
"We had an amazing week swimming, hiking, paddling, and admiring gorgeous Lake Amherst. All of our favorite things were nearby - lovely hiking trails, and maple ice cream. Perfect location, well appointed kitchen, and perfect dock on the lake. Our family loved every moment and we hope to come back again."
New Lakeside Cottage near Okemo and Killington
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Fridge, microwave, oven, stovetop

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great location close to Killington. Accurate listing. Nothing fancy but all the necessities available. Was clean and comfortable. Driveway was plowed early for easy access in/out."
The price is SAR 619
SAR 1,925 total
includes taxes & fees
16 Mar - 17 Mar
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Cozy Cabin Retreat
1 bedroom, iron/ironing board, travel crib, free WiFi

Cozy Cabin Retreat

10.0 out of 10, Exceptional, (26)
"The property was perfect and quiet. The hosts were quick to respond and gave great directions and advice. Will definitely stay again."
Cozy Cabin Retreat
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Exterior

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (9)
"If you’re looking to spend a weekend with some friends at Killington this is definitely the most bang for your buck outside of the resort. 20 minute drive and plenty of plowed parking. "
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Idyllic Wallingford Retreat - Near Skiing & Hiking
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, cookware/dishes/utensils

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was the perfect place for 2 people to stay for a trip to Okemo. Everything we could have needed was available on the property, it was very clean and comfortable, and the hostess was great at communicating details ahead of time. Thanks for allowing us to use your property - I would love to return!"
Idyllic Wallingford Retreat - Near Skiing & Hiking
Rustic Roxbury Ski Farmhouse With Trails!
Books

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!
Pet-friendly Roxbury Farmhouse on 350 Acres!
House (4 Bedrooms) | Interior

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!
Lovely Brookfield Home w/ Private Deck & Views
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Lovely Brookfield Home w/ Private Deck & Views

3.0 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home w/ Private Deck & Views
Killington Area Escape w/ Deck, Views & Hot Tub!
Interior

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
House (6 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Lakefront Paradise Near Okemo & Killington
Interior

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Inviting A-frame Cabin w/ Saltwater Hot Tub!
Interior

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!
Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.
Outdoor dining

Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.

Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.
Newly remodeled cottage at Lake Dunmore!
Terrace/patio

Newly remodeled cottage at Lake Dunmore!

Newly remodeled cottage at Lake Dunmore!
Ski, Hike & Fish: Modern Rutland Home
Interior

Ski, Hike & Fish: Modern Rutland Home

3.0 star property
Ski, Hike & Fish: Modern Rutland Home
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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Other property types in Pittsfield

Killington Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
Mountain Green
Indoor pool

Mountain Green

2.0 star property
5.8 out of 10, (8)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 860
SAR 1,154 total
includes taxes & fees
23 Mar - 24 Mar
Mountain Green
Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (233)
"We thoroughly enjoyed our 3 nights at Little Loft. We needed some R&R and that’s exactly what these few days were. We grilled, enjoyed the view with a snowy day/night, melted in the hot tub, and chilled by the fireplace at night. The cabin had everything we needed and then some. Communication was perfect. We couldn’t have asked for a better experience."
Cozy Loft for two with Hot Tub & Mtn 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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