5 Best Vacation Rentals in Pittsfield - Holiday Lettings - Cabins

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214 Vacation rentals

(2) Very Good 

27

Home rental in Pittsfield

Vermont / Pittsfield

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
This secluded mountain home is located in the small town of Pittsfield, VT just minutes away from one of the most scenic drives in New England, Route 100. Surrounded by national forest with stunning views of the Green Mountains, this is the perfect place to get away wit …see more

from $150 / night

$600 - $2,700 / week

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from $150 / night

(1) Excellent 

16

Vacation home rental

Vermont / Pittsfield

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
Location: Killington, Vermont, USA (Pittsfield - 8 miles to Killington slopes) Accommodations: House, 5 Bedrooms + living room, Den, game room, dining room (Sleeps 11) Set on a private road in the hills of historical Pittsfield, our house welcomes you – winter, spring …see more

from $350 / night

$2,000 / week

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from $350 / night

(1)  

26

Vacation home in Pittsfield

Vermont / Pittsfield

3 20 Min stay varies

  • 3 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Pet friendly
Come ski Killington and Pico Peak mountains while staying in one of the loveliest Killington vacation condos for rent. This lovely Vermont Chalet located only 7 miles and a 15-minute drive from the Killington access road and shops! This beautiful Vermont Chalet is locat …see more

from $363 / night

$2,178 - $3,090 / week

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Responds fast!
avg. 1 hour 27 minutes

from $363 / night

32

Pittsfield Vacation home rental

Vermont / Pittsfield

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Pet friendly
Pittsfield, Vermont is like something out of a greeting card with true old school Vermont charm, only 15 minutes from the slopes but miles from the hustle and bustle. If you are looking for some quiet relaxation and a place to enjoy your family and friends, you will fin …see more

from $500 / night

$3,500 / week

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Responds fast!
avg. 48 minutes

from $500 / night

25

Vacation home in Pittsfield

Vermont / Pittsfield

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Enjoy all of the amenities available to you in this lovely condo - like a shared sauna and hot tub (available only during the colder winter months) - and settle in for a vacation filled with the perfect balance of R&R and outdoor fun! Located in the Wintergreen communi …see more

from $111 / night

$777 / week

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Responds fast!
avg. 2 hours 56 minutes

from $111 / night