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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 41 Cottages in Pittsfield with updated reviews, rates, and availability.

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
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 AED 459
AED 720 total
includes taxes & fees
26 Mar - 27 Mar
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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
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 AED 574
AED 1,843 total
includes taxes & fees
26 Mar - 27 Mar
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
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
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.
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
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
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
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!
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!
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!
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!
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
Lakefront Paradise Near Okemo & Killington
Interior

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington
Charming Updated Cottage
Fridge, microwave, oven, stovetop

Charming Updated Cottage

Charming Updated Cottage
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
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, (116)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
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)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!
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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