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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Luxury 1 Bedroom with Stratton View

Summit View Road Winhall VT

Price$14,000

Est. Mortgage: $/month

Listing Number 111

  • Non-MLS Vacation Rentals
  • Resort name Stratton
  • Bathroom 1
  • Maximum Occupants 4
  • Bedrooms 1

Enjoy huge mountain views from this 1 bedroom/1 bath apartment in Stratton's High Meadow area.  Modern compact kitchen, private entrance, ski storage and a shuttle to the base that picks you up at your door.   New comfortable furniture and open dining area complete this great rental. 

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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3 Bedroom Intervale on Shuttle Route

Winhall VT

Price$25,000

Est. Mortgage: $/month

Listing Number 101

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Bedrooms 3
  • Shuttle service

Conveniently located in Intervale at Stratton, this light-filled 3 bedroom/3 bath condo features an open kitchen and dining area, spacious living room with wood-burning fireplace, and a jacuzzi tub in the master bath.  Bunks for the kids and a loft for extra space make this a great property to enjoy winter in Vermont.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Farmhouse in Southern Vermont

Stowell Hill Londonderry VT 05148

Price$11,000

Est. Mortgage: $/month

Listing Number 900

  • Non-MLS Vacation Rentals
  • Bathroom 2
  • Bedrooms 3
  • Type Winter Seasonal
  • Sleeps 6

Elegant and well maintained farm house with charming accents that will make your stay enjoyable.  The open kitchen and dining room are a beautiful tribute to years past with modern touches for covenience.  The library and sitting room on the lower level are inviting and ready for you to maek yourself at home.  Upstairs boasts three bedrooms with the touch of a true country farmhouse.  The bathroom is spacious and heated for your convenience.  The oil baseboard heat runs through the downstairs and a pellet stove warms the mudroom.  No oil does not ciruclated upstairs but previous renters have found that a heated blanket or room heaters made it nice and cozy.   The home also comes with a detached garage for your convenience and plenty of acreage to make your own cross-country trails.  This is a spectacular find for your winter seasonal rental in the green mountains.  Only a short drive to four of the top ski resorts in the area (Okemo, Magic, Bromley and Stratton).  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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4 Bedroom Home Near Stratton & Bromley

Old Route 30 Winhall VT 05340

Price$15,000

Est. Mortgage: $/month

Listing Number 990

  • Non-MLS Vacation Rentals
  • Bathroom 2
  • Bedrooms 4
  • Sleeps 10

Spacious 4 bedroom/2 bath home conveniently located between Stratton and Bromley.  Renovated kitchen, back and front porches, garage, and fully equipped for a family to move right in and enjoy.  15 minutes to Manchester's dining and shopping, 10 minutes to Stratton or Bromley.  The living room has a charming wood-burning fireplace and room for game nights by the fire.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Upgraded Strattonwald house

Red Brook Road Winhall VT 05340

Price$26,000

Est. Mortgage: $/month

Listing Number 890

  • Non-MLS Vacation Rentals
  • Bedrooms 4
  • Type Winter Seasonal
  • Shuttle service
  • Sleeps 8

Updated throughout & immaculately cared for home overlooking a running stream.  Located in the much deesired Strattonwald development the rental offers Winter Shuttle on weekends and holidays.  Plenty of room to relax enjoy the fireplace and hot tub after a long day on the slopes.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Luxury Treetop Townhome

Viburnum Way Stratton VT 05155

Price$37,000

Est. Mortgage: $/month

Listing Number 889

  • Non-MLS Vacation Rentals
  • Village Stratton
  • Bedrooms 3
  • Type Winter Seasonal
  • Shuttle service

Beautiful three bedroom four bath Tree Top townhome with family room. Ski-home (ski-off), on-mountain townhouse.This home has many custom furnishings made by Skip Woodruff including a built in double bunk set, a Murphy bed in the family room, bathroom mirrors, and many more custom pieces by Salamander Designs. Enjoy the views from your private hot tub just outside your fabulous ski town home. Tree Top offers shuttle to the lifts and village.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Piper Ridge with a view

Cobble Ridge Road Stratton VT

Price$28,000

Est. Mortgage: $/month

Listing Number 898

  • Non-MLS Vacation Rentals
  • Bedrooms 3
  • Type Winter Seasonal
  • Shuttle service
  • Sleeps 10

LOCATION! LOCATION! LOCATION! Piper Ridge is a well sought after community in Stratton with winter shuttle and a sports center to enjoy all winter long.  With updated kitchen and nicely appointed furnishings this unit will make you feel comfortable and relaxed.  A fire place on both floors and an enclosed hot tub is sure to top off your stay.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Newly renovated on the Battenkill Condo

Battenkill Road Manchester Center VT 05255

Listing Number 888

  • Non-MLS Vacation Rentals
  • Bedrooms 3
  • Type Winter Seasonal
  • Sleeps 7

Perfect location to everything Manchester and the Mountains.  Shoping, Dining, Hiking and Skiing just minutes away.  Enjoy a nicely appointed home with a fireplace and plenty of living area to enjoy your vacation.  Private entrance and driveway with a back deck to enjoy the views.  Approx. 1400 square feet

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Country home in Landgrove

Ridge Road Landgrove VT

Price$7,000

Est. Mortgage: $/month

Listing Number 875

  • Non-MLS Vacation Rentals
  • Bedrooms 3
  • Type Winter Seasonal
  • Sleeps 6

Adorable country home in Landgrove close to three ski resorts Stratton Mountain, Bromley Mountain and Magic Mountain.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Vermont Ventures Winter Getaway

10 Lake Road Winhall VT 05340

Price$11,500

Est. Mortgage: $/month

Listing Number 816

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Bedrooms 4
  • Listing Type Winter Season

Spacious home in serene setting overlooking a private pond.  It's only 10 minutes to Stratton, 15 to Bromley and 20 to Manchester's shops and restaurants.  Four bedrooms and 2.5 baths, plus a raised hearth fireplace in the living room with a private den.   The lower level has a sauna for  relaxing in after a day on the slopes.  Enjoy meals in the sunny dining area.  Available for a full winter season rental.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

Pearl Buck House

Pearl Buck Drive Winhall VT 05340

Price$35,000

Est. Mortgage: $/month

Listing Number 752

  • Non-MLS Vacation Rentals
  • Property Name Pearl Buck House
  • Type Winter Seasonal
  • Sleeps 12

Its all about the view and it doesnt get any better! RENTAL DATES:  JANUARY 10, 2020 to APRIL 10, 2020 Enjoy views of Magic, Ascutney, Bromley, Okemo, Killington, Equinox, Stratton and Mt snow. This 1960's custom contemporary has recently had a major renovation. The main living areas have radiant heat flooring including separate thermostats for each bedroom. The pool table room is a great entertainment area. The TV room has a 72"' Sony TV. The kitchen family room and dining layout is perfect for entertaining. 

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

Hells Peak - Great Location for all 3 Mountains

Hells Peak Londonderry VT 05148

Price$11,000

Est. Mortgage: $/month

Listing Number 720

  • Non-MLS Vacation Rentals
  • Bedrooms 3
  • Type Winter Seasonal
  • Sleeps 8

This Vermont Farmhouse has stunning views of Magic Mountain!  On 64 acres of land there is plenty of room to enjoy your vacation including your very own sledding hill.  The lease requires a professional cleaning once a month.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Black Bear #2

Middle Ridge Road Stratton VT 05360

Price$15,000

Est. Mortgage: $/month

Listing Number 706

  • Non-MLS Vacation Rentals
  • Winter Rental
  • Property Name Black Bear #2
  • Bedrooms 3
  • Type Winter Seasonal

Location is the key!  This chalet co-op is located by the Black Bear Lodge and a short walk to the Stratton Village. This 3 bedroom sleeps 7 and has 2 baths.  New appliances!    

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Strattonwest 2 Bedroom

Stratton Access Road Winhall VT 05340

Price$8,000

Est. Mortgage: $/month

Listing Number 668

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Resort name Stratton
  • Bathroom 1

Cozy 2 bedroom/1 bath condo in Stratton West is just a mile from Stratton's base.    

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Trailside Luxury

24 Sawmill Road Stratton VT

Price$50,000

Est. Mortgage: $/month

Listing Number MS30

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Resort name Stratton
  • Bathroom 5

True trailside luxury in this 5 bedroom/5 bath custom built home at Stratton.  Front sitting room with double-sided marble fireplace, large living room, dining room and chef's kitchen.  Two master bedrooms with ensuite baths, third level with 3 additional bedrooms.  Lower level gameroom with pool table and ping pong, full family room, garage and large entry mudroom.  Back deck overlooks the private wooded back lot.  Exquisite furnishings and bedding.  Walk/ski to the Lower Wanderer Trail.   This property is listed for sale and lease will include a buy out clause.    

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Private 3 Bedroom Modern Home

Loop Road Winhall VT

Price$19,000

Est. Mortgage: $/month

Listing Number W42

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Resort name Stratton
  • Bedrooms 3

Enjoy a private wooded setting minutes from Stratton in a custom modern home.  Large sunny living room with stone floors, large raised hearth fireplace and comfortable furniture.  Open kitchen with island and new appliances is adjacent to the dining area and a half bath is in the hall.  The master bedroom has a king bed and full bath. Up the spiral staircase are 2 additional bedrooms: one with twin beds and one with a queen bed and full bath.  A third bath is in the upstairs hall along with a queen bed tucked into the loft over the dining area.  Large deck with gas grill. 

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

Stratton Gardens Estate

Stratton Gardens Winhall VT

Price$39,500

Est. Mortgage: $/month

Listing Number 168

  • Non-MLS Vacation Rentals
  • LocationType Stratton Gardens
  • Winter Rental
  • Bedrooms 4
  • Type Winter Seasonal

Beautifully decorated and maintained home off the Stratton Access Road.   Beautiful floor to ceiling fieldstone fireplace in living room.  Family room with gas fireplace and access to outdoor hot tub.   Premium appliances in the updated kitcheck.  House has four zone heating plus a heated two car garage.    House presently listed for sale. Stratton Shuttle on weekends and holidays.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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5 Bedroom Contemporary with Huge Views

25 Benson Fuller Drive Winhall VT 05340

Price$28,000

Est. Mortgage: $/month

Listing Number 140

  • Non-MLS Vacation Rentals
  • Summer Rental
  • LocationType Winhall
  • Winter Rental
  • Resort name Stratton

Short drive to the Stratton base/village. High ceilings and open floor plan make this house perfect for entertaining large families. Huge windows throughout the house offer lots of light throughout the day and spectacular views. Three massive stone wood-burning fireplaces in the main living area, den and master bedroom. Main floor contains a large dining area, spacious great room with oversize leather couches, open kitchen, master bath has jacuzzi tub. Lower level has bedroom, bonus room, and full bathroom, as well as a den with wet bar, pool table and flat-screen TV.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Vantage Point 2 Bedroom

East Birch Rd. Stratton VT

Price$600

Est. Mortgage: $/month

Listing Number VP7

  • Non-MLS Vacation Rentals
  • Summer Rental
  • LocationType Vantage Point
  • Winter Rental
  • Resort name Stratton Mountain

Convenient to the slopes with great views, this 2 bedroom/2 bath Vantage Point condominium features a new kitchen with granite counters, a living room with wood-burning fireplace, shuttle to the slopes, and is walking distance to Stratton's Sports & Fitness center. Rental rates are per night and are subject to a 15% VT tax and service charge and an exit cleaning fee. $325 per night summer rate.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Landmark Ski In/Ski Out

19 Village Lodges Road Stratton VT 05155

Listing Number 452

  • Non-MLS Vacation Rentals
  • Village Stratton Mountain
  • Title Landmark
  • LocationType In Village
  • Winter Rental

It doesn't get more convenient than this 2 bedroom/2 bath luxury Landmark condominium overlooking the slopes! This unit has 2 bedrooms, one room with a king bed and the second with two bunks, sleeping 6 comfortably. Open kitchen with granite counters and high-end appliances, gas fireplace in the living room and big views of the mountain. Enjoy the award-winning restaurant Verde on the building's main level. Includes 1 preferred parking spot, ski locker in the lobby and a fully equipped game room with fireplace and pool table off of the lobby.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Landmark

Landmark Stratton VT

Price$50,000

Est. Mortgage: $/month

Listing Number 230

  • Non-MLS Vacation Rentals
  • LocationType Clocktower Building
  • Winter Rental
  • Complex Landmark
  • Resort name Stratton

Location! Location! Location!  This condo is located in Stratton Village with Verde Restaurant on the first floor.  You can't get much closer to Stratton Mountain's Gondola.  It has a queen bed, 2 sets of bunks and a sleeper sofa.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Quaint Vacation Home

867 Goodaleville Road Jamaica VT 05343

Price$10,000

Est. Mortgage: $/month

Listing Number 225

  • Non-MLS Vacation Rentals
  • LocationType Goodaleville Road
  • Winter Rental
  • Resort name Stratton
  • Bathroom 3

Quaint vacation home on country road close to Stratton Mountain

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

Forest Farms

68 Sugarbush Drive Winhall VT

Price$12,500

Est. Mortgage: $/month

Listing Number 126

  • Non-MLS Vacation Rentals
  • Winter Rental
  • Resort name Stratton
  • Bathroom 2
  • Property Name Forest Farms

Very nice Rustic Vermont Style home within 4 miles to Stratton's Base Lodge. It sleeps 8 comfortably. 

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Country Home

Winhall Station Road Londonderry VT 05155

Listing Number 98

  • Non-MLS Vacation Rentals
  • Description Title Winhall Station
  • LocationType Winhall Station Road
  • Winter Rental
  • Resort name Stratton

Very private, great views of fields & mountains. Adjacent to Campground for hiking, cross-country skiing & snow-mobiling.  Very quiet.

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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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Intervale Condo

Intervale Winhall VT

Price$21,000

Est. Mortgage: $/month

Listing Number 261

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Winter Rental
  • Complex Intervale
  • Resort name Stratton

This 3 bedroom unit with 2  master suites plus loft townhome in Intervale has a winter shuttle to Stratton, open living and dining area overlooking wooded privacy, and 3 full baths.  Full laundry, mud room entry and wood burning fireplace for apres ski enjoyment.  

Listed by William Raveis Winhall Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* 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 A VisitAsk A QuestionMore Details

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Copyright 2019 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 16, 2019.