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Vacation Rentals in Pittsfield, Vermont

about Pittsfield

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Pittsfield, Vermont vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Pittsfield are added and updated every week!

Compared to hotels, Pittsfield vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Pittsfield, Vermont Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Pittsfield things to do


Pico Mountain At Killington

To Hell with skiing here in the winter, they have the Alpine Slide (summer only) which is a terribly fun way to spend a beautiful day in Vermont. Keep more


Root's Ski & Snowboard Shop

Friendly staff, reliable rentals, we love coming here every trip to Killington! just wish they accepted amexread more


Green Mountain National

An absolute must play. This course is gorgeous, the mountains are in full view at all times. The people were incredibly friendly and welcoming. No more


BigTown Gallery

If you're in the vicinity, you MUST stop by this gallery. The owner/curator has such exquisite taste -and it's not just an art exhibit space--in the more


Killington Resort

Second time here, although this time I actually know what I'm doing on the snowboard. The trails are well groomed, this last weekend I went it wasn' more


Vermont River Tubing

Great time with my 6-year-old. We took our time coming down the river and spent 4 hours floating and swimming. Next time I'd probably rent a paddle to go more


Norman Rockwell Museum of Vermont

This is vastly different than the museum in Stockbridge, MA. This is much more of a roadside attraction type of place. Admission is cheap, and more


Spa At the Woods the

I went this past Saturday with my boyfriend for a couples massage. We were lucky that it was a slow weekend - we basically had the whole place to more


Killington Boot Camp

Boot camp changed my life last year. I had been mindlessly running for years.. not pushing myself or going any further. Luckily a girl friend told more


Bulldog Fishing Charters

Awesome Charter boat! Lots of fish and more


Green Mountain Rock Climbing Center

Very fun, friendly staff and GREAT military discount! Our kids loved it!read more

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Cedar Rock Chalet - New Outdoor Hot Tub - 15 Min to Killington
Pittsfield Chalet Rental Picture
  • bedrooms 3
  • rental type Chalet
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $265 - $480 /nt
    $1,325 - $3,360 /wk
    $4,320 - $10,752 /mth

26 reviews write a review

Mountain Chalet - Killington Area
Pittsfield Chalet Rental Picture
  • bedrooms 4
  • rental type Chalet
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (USD) $150 - $400 /nt

3 reviews write a review