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Pittsfield Holiday Rentals

Hotels (0)

B&Bs / Inns (3)

Speciality Lodging (0)

Holiday Rentals (125)

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[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Meadows, Pittsfield
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 12
Bathrooms: 4
Spacious kitchen and dining area. The large master suite has a private deck and private bath with whirlpool tub. Lower level includes game room with pool ...
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Serenity, Pittsfield
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Located off of scenic Rt 100 in Pittsfield, nestled in the Hawk Mountains, Serenity combines tasteful elegance with a beautiful mountain country wooded ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 1
You can relax in the the outdoor hot tub before warming your feet at the woodstove fireplace in your living room. Featuring a spacious kitchen and living ...
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The following rentals are within 40 kilometres of Pittsfield, Vermont.

Contact Manager
Nightly rate from
£153
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 10
Bathrooms: 3
The Lodges are upscale 3 bedroom 3 bathroom accommodations right in the heart of Bear Mountain, walking distance to your own private lift. These upscale ...
  • Nightly
    £153 - £416
  • Weekly
    £1,067 - £2,547
  • Monthly
    £4,810 - £9,860
Contact Manager
Nightly rate from
£127
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Whiffletree Condominiums are centrally located in the heart of Killington's main basin area. In winter, a shuttle runs to Snowshed lodge, only 1/2 mile away, ...
  • Nightly
    £127 - £283
  • Weekly
    £885 - £1,721
  • Monthly
    £4,030 - £6,671
Vista View, Killington
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 10
Bathrooms: 3
One of the plushest homes you'll find in Killington, this 3 bedroom/2.5 bath gorgeous private home features a grand piano, 65" TV and a hot tub on the deck ...
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Contact Owner
Nightly rate from
£93
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
This 2 bedroom 2 bath condo is located at the Mt. Green Resort. It is at the base of Killington so you can walk to the lifts. It is on the top floor ...
  • Nightly
    £93 - £278
  • Weekly
    £247 - £1,636
  • Monthly
    £741
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 2
Bundle up, strap on your gear and you're ready to ski or ride to the Skyeship Gondola and base lodge right from your back door! Stay at Spruce Glen and ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
The Woods Resort & Spa leads the area in premium, distinctive condominium and townhouse accommodations. Centrally located on Killington’s Access Road, ...
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Presario, Killington
Contact Manager
Nightly rate from
£648
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 12
Bathrooms: 4
You know you are somewhere special as soon as you pull up the drive of this majestic overlook. Unique in design, it is not your typical Killington vacation ...
  • Nightly
    £648 - £1,149
  • Weekly
    £5,965 - £7,368
  • Monthly
    £25,208 - £27,580
Contact Manager
Nightly rate from
£147
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Enjoy the laid back, quieter atmosphere of Pico Mountain at Killington, featuring 48 trails and 7 lifts, a perfect way for families to enjoy a day of skiing. ...
  • Nightly
    £147 - £354
  • Weekly
    £1,027 - £2,167
  • Monthly
    £4,638 - £8,393
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 2
Bundle up, strap on your gear and you're ready to ski or ride to the Skyeship Gondola and base lodge right from your back door! Stay at Spruce Glen and ...
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Woods Resort A8, Killington
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 3
The Woods Resort & Spa leads the area in premium, distinctive condominium and townhouse accommodations. Centrally located on Killington’s Access Road, ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 1, sleeps 6
Bathrooms: 2
The Woods Resort & Spa leads the area in premium, distinctive condominium and townhouse accommodations. Centrally located on Killington’s Access Road, ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
This 2 bedroom condo contain the most widely requested features for the recreational skier; continuous shuttle service will carry you to the lifts and there ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
The Woods Resort & Spa leads the area in premium, distinctive condominium and townhouse accommodations. Centrally located on Killington’s Access Road, ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 1, sleeps 4
Bathrooms: 1
Ski right home when you stay at Edgemont! Located at the end of a trail coming home from Snowshed, these 1 bedroom units contain the most widely requested ...
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Contact Manager
Nightly rate from
£262
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 10
Bathrooms: 3
At The Sunrise Village, you truly "have it all". Sunrise is an ideal area for families and couples who want to get away from the crowds of Killington’s main ...
  • Nightly
    £262 - £729
  • Weekly
    £1,832 - £4,452
  • Monthly
    £8,087 - £17,218
Woods Resort E5, Killington
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 4
The Woods Resort & Spa leads the area in premium, distinctive condominium and townhouse accommodations. Centrally located on Killington’s Access Road, ...
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Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns