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Woodstock Vacation Rentals

Hotels (4)

B&Bs / Inns (16)

Specialty Lodging (0)

Vacation Rentals (127)

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There are no vacation rentals within Woodstock, Vermont. We broadened your search to include all rentals within 25 miles.

Vista View, Killington
Management: Professional
Property: Rental Home
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
$180
Management: Verified owner
Property: Rental Home
Bedrooms: 3, sleeps 4
Bathrooms: 1
Min stay:2
Our renovated farmhouse sits on a hillside meadow surrounded by open fields and forest. The views from the house sweep from Mount Ascutney to the south, to ...
  • Nightly
    $180 - $245
  • Weekly
    $1,085
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Management: Professional
Property: Rental Home
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: 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 ...
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Woods Resort F3, Killington
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 9
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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Contact Manager
Nightly rate from
$201
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
    $201 - $799
  • Weekly
    $1,012 - $4,175
  • Monthly
    $6,143 - $11,129
Serenity, Pittsfield
Management: Professional
Property: Rental Home
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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Meadows, Pittsfield
Management: Professional
Property: Rental Home
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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Nightly rate from
$205
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Min stay: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
    $205 - $811
  • Weekly
    $1,433 - $4,264
  • Monthly
    $6,526 - $11,512
Contact Manager
Nightly rate from
$238
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
    $238 - $693
  • Weekly
    $1,663 - $4,009
  • Monthly
    $7,511 - $13,593
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: Rental Home
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 E11, 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: 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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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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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