10 Best Vacation Rentals in Pittsfield - Holiday Lettings - Cabins

Close

View larger map

Pittsfield

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

11 Vacation rentals

(1) Excellent 

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 / week

Book View

from $150 / 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 - $3090 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $363 / night

31

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 of …see more

from $395 / night

$2766 - $6300 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from $395 / 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

Book View

from $300 / night

36

Vacation apartment in Pittsfield

Vermont / Pittsfield

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Suitable for children age 5+
This home is set along the Tweed River just before the scenic Village of Pittsfield. Rustic, secluded with total privacy. Cell phone sercie is spotty and 4 wheel drive vehicles are required. Only a short 10 minutes drive to the Killington ski resort. The home is sp …see more

from $665 / night

$4655 - $10045 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from $665 / night

30

Home rental in Pittsfield

Vermont / Pittsfield

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Nestled in the heart of the Green Mountains is where you will find Lookout, a luxurious 3 Bedroom 3 bath private home, large front porch with awesome views and a large back deck with a gas grill for BBQ's.  It offers an open floor plan with cathedral ceilings and beauti …see more

from $217 / night

$2148 - $3043 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $217 / night

24

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 …see more

from $350 / night

$3290 - $5285 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from $350 / 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 - $3066 / week

Book View

Responds fast!
avg. 2 hours 17 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 picturesq …see more

from $515 / night

$3605 - $6335 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from $515 / 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

Book View

from $450 / night

24

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 be …see more

from $445 / night

$3115 - $6300 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from $445 / night

1