10 Best Vacation Rentals in Pittsfield - Holiday Lettings - Cabins

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10 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 - $2700 / week

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from $150 / night

(1) Excellent 

16

Vacation home rental

Vermont / Pittsfield

5 11 2 nights min

  • 5 bedrooms
  • Sleeps 11
  • 2 nights min
  • 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 $450 / night

$2200 / week

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from $450 / night

33

Vacation home in Pittsfield

Vermont / Pittsfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Wonderful three bedroom two bathroom home located in the mountains of Pittsfield, Vermont - a postcard Vermont town. Hawk Landing is surrounded by lush woods, offering a perfect getaway for families and small groups. Only a short drive to all that Killington has to offe …see more

from $385 / night

$2695 - $6125 / week

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Responds fast!
avg. 1 hour 23 minutes

from $385 / night

56

Vacation home rental

Vermont / Pittsfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
LookOut! .... this recently constructed, 3 bedroom 3 bathroom large lovely secluded home is nestled in the heart of the Green Mountains. It's expansive, open concept, main floor is perfect for entertaining large groups or just enjoying an intimate dinner for two. It's g …see more

from $350 / night

$3290 - $5285 / week

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Responds fast!
avg. 1 hour 23 minutes

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 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 located on the side of a high mountain right off picturesque Ro …see more

from $363 / night

$2178 - $4480 / week

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Responds fast!
avg. 1 hour 41 minutes

from $363 / night

28

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 $99 / night

$693 / week

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Responds fast!
avg. 2 hours 55 minutes

from $99 / night

56

Vacation home in Pittsfield

Vermont / Pittsfield

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Pet friendly
Your home away from home! Whether you are looking for peace and relaxation or convenience and accessibility, the Blue Diamond House is the perfect mountain retreat. Tastefully appointed, warm and inviting, you will love stepping into this charming home. Three beau …see more

from $435 / night

$3326 - $6755 / week

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Responds fast!
avg. 1 hour 23 minutes

from $435 / night

11

Pittsfield Vacation home rental

Vermont / Pittsfield

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
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 $300 / night

$999 / week

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from $300 / night

30

Home rental in Pittsfield

Vermont / Pittsfield

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Pet friendly
Your home away from home! Whether you are looking for peace and relaxation or convenience and accessibility, the Blue Diamond House is the perfect mountain retreat. Tastefully appointed, warm and inviting, you will love stepping into this charming home. Three beautiful …see more

from $280 / night

$2160 - $4585 / week

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Responds fast!
avg. 1 hour 41 minutes

from $280 / night

24

Vacation chalet 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 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 located on the side of a high mountain right off picturesque …see more

from $550 / night

$3850 - $6790 / week

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Responds fast!
avg. 1 hour 23 minutes

from $550 / night