Winter Seasonal Rentals

18Results

This page features winter seasonal rentals available in your desired location. Explore the unique offerings that cater to seasonal needs and enjoy the beauty of winter. Browse the listings below to find your next rental.

Newest
New Listing
8 Kendall Farm Road Winhall VT 05340

$19,500/season

Winhall, VT

8 Kendall Farm Road

  • 3 Beds
  • 3 Baths
  • 6 Days on Market
MLS#: 5112115
New Listing

$16,000/month

Jamaica, VT

29 Pikes Falls Road

  • 4 Beds
  • 2 Baths
  • 23 Days on Market
MLS#: 5109606

$18,000/month

Jamaica, VT

22 Reynolds Lane

  • 3 Beds
  • 3 Baths
  • 85 Days on Market
MLS#: 5099486

$34,000/season

Winhall, VT

35 Strattonwald Road

  • 4 Beds
  • 3 Baths
  • 414 Days on Market
MLS#: 5056988
New Listing

$4,000/month

Manchester, VT

59-29 Murray Hill Heights Drive, Unit 29

  • 2 Beds
  • 3 Baths
  • 4 Days on Market
MLS#: 5112667
New Listing

$12,500/season

Londonderry, VT

23 Old School Road, Unit the Barn

  • 1 Bed
  • 1 Bath
  • 4 Days on Market
MLS#: 5112665
New Listing

$17,500/season

Stratton, VT

28 Canedy Road

  • 2 Beds
  • 1 Bath
  • 5 Days on Market
MLS#: 5112384
New Listing

$7,000/month

Dorset, VT

195 Mystic Lane

  • 4 Beds
  • 5 Baths
  • 13 Days on Market
MLS#: 5111185

$2,500/month

Londonderry, VT

23 Old School Road, Unit the Barn

  • 1 Bed
  • 1 Bath
  • 39 Days on Market
MLS#: 5107186

$2,800/month

Jamaica, VT

4591 Vt Route 30

  • 4 Beds
  • 2 Baths
  • 44 Days on Market
MLS#: 5106312

$2,500/month

Manchester, VT

293 Barnumville Road

  • 3 Beds
  • 2 Baths
  • 54 Days on Market
MLS#: 5104837

$4,250/month

Manchester, VT

9 Murray Hill Road South, Unit 9

  • 3 Beds
  • 3 Baths
  • 62 Days on Market
MLS#: 5103518

Winter Seasonal Rentals, City, VT

Winter seasonal rentals provide an opportunity to experience the charm of the winter months in this picturesque region. With access to stunning landscapes and outdoor activities, these rentals are situated near popular ski resorts and winter sports areas. The surrounding area boasts beautiful trails for snowshoeing and cross-country skiing, making it a prime location for winter enthusiasts. Additionally, the community offers a variety of local shops and dining options, creating a welcoming atmosphere for visitors and residents alike.

Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 6, 2026 8:39 AM EDT