Vermont Winter Rental Homes

Find your next winter vacation rental home in one of Southern Vermont's surrounding towns.

Stratton Seasonal Winter Rentals

Contact William Raveis Winhall Real Estate at 802-297-1550 or online if you're interested in a particular rental property or have any questions.

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Alta Road

Alta Road Winhall VT 05340

Winhall, VTAlta Road

Rental Price$25,000

For Rent

Listing Number X58221311

  • Exclusive Vacation Rentals
  • min rental period winter seasonal
  • Date Available 11/15/2023
  • Winter Rental
  • LocationType Winhall

Charming chalet is the perfect spot to savor the winter in Vermont.  Enjoy a fully equipped kitchen and two living rooms. With close proximity to skiing at Stratton, Bromley and Magic Mountains, as well as to restaurants and shopping, there is no doubt you will create lasting winter memories here.  

Listed by Carrie Mathews of William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Parker House

Pike Falls Road Jamaica VT 05343

Jamaica, VTPike Falls Road

Rental Price$22,000

For Rent

Listing Number X34644583

  • Exclusive Vacation Rentals
  • min rental period winter Seasonal
  • Date Available 11/17/2023
  • Winter Rental
  • LocationType Jamaica

Spend your winter in this quintessential Vermont farmhouse, just 10 miles from Stratton Ski Resort, and close to Bromley and Magic Mountains.  This home boasts 3000 square feet of living space, two baths, a game room with a pool table, fast Wifi, and sleeps 10 comfortably.  Enjoy the huge farm table, living room, sun room, private backyard, and fire pit.  The Parker House is one of the oldest homes in Jamaica village.  It remains full of authentic integrity and charm with a large eat-in kitchen, living room, three bedrooms down and one large, open-concept bedroom upstairs with its own bath and shower.  There is a full bathroom downstairs.  The house is outfitted with all the comforts of home, including full house oil heat, a pellet stove in the living room, and a wood stove in the game room/library.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1800s Greek Revival

Jamaica VT 05343

Jamaica, VT

Rental Price$20,000

For Rent

Listing Number X90607673

  • Exclusive Vacation Rentals
  • Village Jamaica
  • Winter Rental Price $20,000
  • Date Available 11/17/2023
  • LocationType Jamaica

This family and pet-friendly 1800s Greek Revival home is in the center of Jamaica Village with over 2500 square feet of living space.  Just 10 minutes to Stratton Mountain Ski Resort and 25 minutes to Manchester or Mount Snow, this home has been lovingly cared for, and boasts both comfort and style.  There is a covered porch and small deck and veranda for relaxing outside.  Walk to Jamaica State Park and West River for recreation, village eateries, a hot yoga studio, library, and a general store.  This house has an enormous master bedroom, and three additional nice-sized bedrooms.  There is a large, well-equipped chef's kitchen with a center island, and a formal dining room that seats eight, as well as sprawling living room.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1850s Farmhouse

1850s Farmhouse Jamaica VT 05343

Jamaica, VT1850s Farmhouse

Rental Price$18,000

For Rent

Listing Number X52491453

  • Exclusive Vacation Rentals
  • Title 1850s Farmhouse
  • Winter Rental Price $18,000
  • Winter Rental
  • Date Available 11/17/2023

This lovely 1850s antique farmhouse, with a private, spacious backyard that backs up to the river, is rich with history and charm.  With original wide pine floors, plaster walls, a slate roof, and classical lines, you will get a true taste of Vermont's beautiful architecture nestled in a bowl of mountains.  The home is situated in a sweet walking village with the best beer/wine selections.  Offering 4 bedrooms and fresh Vermont mountain air, life feels a bit simpler here!  With Vermont's best skiing resorts a mere 15 minutes away, a firepit in the backyard for gathering, as well as a crackling wood stove in the barn, you'll enjoy a quintessential Vermont winter at this gem.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Beaver Hollow Winter Rental

Beaver Hollow Londonderry VT

Londonderry, VTBeaver Hollow

Rental Price$18,000

For Rent

Listing Number X94062077

  • Exclusive Vacation Rentals
  • Winter Rental
  • Date Available 11/01/2023
  • LocationType Londonderry
  • min rental period winter Season

This home features Magic Mountain views to entice you to gear up and hit the slopes.  It is fully updated and just a short walk to Lowell Lake where you can enjoy a picturesque hike.  Enjoy all the Vermont winter attractions including Stratton Mountain, Bromley Mountain, restaurants and shopping within close proximity to this lovingly maintained retreat.  

Listed by Carrie Mathews of William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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The Yellow Sweetie

VT Route 30 Jamaica VT 05343

Jamaica, VTVT Route 30

Rental Price$16,000

For Rent

Listing Number X20118103

  • Exclusive Vacation Rentals
  • Date Available 11/17/2023
  • Winter Rental Price $16,000
  • Title Yellow Sweetie
  • Winter Rental

The Yellow Sweetie is located in a quiet setting at the base of Stratton mountain, just 1 minute to the Stratton Resort Access Road and 8 minutes to the slopes. This adorable home offers stylish country living-meets-shabby chic comfort and coziness.  It is children and pet-friendly and sleeps 4 people. If you need more room, there is a pull-out sofa making the house comfortable for 6.  Each of the two bedrooms has a queen-size bed.  It also has two full bathrooms, one upstairs and one down.  All the comforts of home are available here including a large cook stove, speedy wifi, a Roku smart streaming TV, a DVD player and DVDs, a washer and dryer, a standing shower, and even a clawfoot tub!

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Potter Place

Williams Street Jamaica VT 05343

Jamaica, VTWilliams Street

Rental Price$16,000

For Rent

Listing Number X66753847

  • Exclusive Vacation Rentals
  • Winter Rental
  • min rental period winter Seasonal
  • Title Potter Place
  • Winter Rental Price $16,000

Have you ever been lulled to sleep by the sound of a rushing river?  You will at the Potter Place, perched above the river and overlooking the adorable village of Jamaica, only 15 minutes from Stratton Mountain and close to Magic, Bromley, and Mount Snow.  This fully-outfitted home will offer you the best of Southern Vermont right in walking distance, including Jamaica State Park, a fabulous general store, rivers and waterfalls, and of course--mountains!!  With three bedrooms and one bathroom, this house comfortably sleeps 6 people.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Harwood Place

159 Harwood Place West Townshend VT 05359
For Rent

Listing Number X11089818

  • Exclusive Vacation Rentals
  • LocationType West Townshend
  • Date Available 11/27/2023
  • Winter Rental Price $12,000
  • Title Harwood Place

The dreamy view from this cozy cottage will not only invite you to sit back and stay awhile but provides a show on snowy nights when you can see the groomers on Stratton Mountain working hard to ready the slopes for your next day of skiing.  With three bedrooms and 1.5 baths, you'll have plenty of room for the family to wile away a winter evening by the fireplace. All the modern conveniences are available here, and although you'll feel like you're a world away, both Stratton Mountain and Mount Snow are a mere 25-minute drive. Cell phone service is excellent, and high-speed internet and cable are on site.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.18% last updated on Sep 14, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2023 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 September 21, 2023 11:26 AM EDT