Southern Vermont Winter Rentals

Scroll down to find all winter rentals available in Southern Vermont. Find a variety of listings rentals near Manchester, Stratton, Mount Snow, and the surrounding area.

Winter Season Rentals Vermont

If you have questions or would like to schedule a showing, contact TPW Real Estate.

Search smarterRegister with our site to save your favorite listings and get updates when similar properties are new to the market.

632 Equinox on the Battenkill Manchester VT 05254

MLS Number 4786459

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Monthly

This beautiful townhouse is available starting 12/1/19. The monthly rate for an annual lease is 3,000.00 per month and 4,000.00 per month on a seasonal basis. There are incredible panoramic views of the Green Mountains and three bedrooms which comfortably sleep six people. This is a wonderful opportunity to rent this lovely home which is just 20 minutes to the slopes in the winter and right in town for The Equine Festival and world class golfing in the summer months.

Listed by Peggy O'Neill of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

60 Spaulding Cavendish VT 05143

MLS Number 4786215

  • Rentals
  • Bedrooms 3
  • Bathroom 4
  • Lease Seasonal
  • Subdivision Castle Hill Resorts

Winter seasonal rental available for the 2019-2020 winter season. Price is $25,000 plus utilities, security deposit, internet. Beautifully appointed three bedroom plus loft with great separation of space. Master bedroom with bath. Two guest rooms with queen beds, each with 3/4 bath. Living room with gas fireplace, fully equipped kitchen and ready for a comfortable holiday in the Okemo Valley area. Easy access to Okemo Mountain about 3 miles away. Dine after skiing at the lovely Castle Resort. Relax in the community heated pool or get a massage at the Aveda Spa. A wonderful location.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

1087 Route100 apt 1 Weston VT 05161

MLS Number 4783189

  • Rentals
  • Bedrooms 1
  • Bathroom 1
  • Lease Seasonal
  • Acreage 24

This cozy one bedroom apartment has beautiful wood features, open kitchen and living area and a second-floor bedroom with two double beds. Located on Route 100 north of Weston Village, convenient to ski and riding at Okemo, Magic and Stratton. Affordable lodging for the weekend ski trips! This property has another apartment and a two bedroom home both available for the winter season

Listed by Jessica Citera of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

1087 Route100 apt 2 Weston VT 05161

MLS Number 4783190

  • Rentals
  • Bedrooms 2
  • Bathroom 1
  • Lease Seasonal
  • Acreage 24

This cozy two bedroom apartment has beautiful wood features, main living on first floor with a quaint kitchen, bedrooms located on 2nd floor each with their own staircase and offering a queen bed. Located on Route 100 north of Weston Village, convenient to ski and riding at Okemo, Magic and Stratton. Affordable lodging for an individual or small group looking to get away for the weekend ski trips! This property has another apartment and a two bedroom home both available for the winter season

Listed by Jessica Citera of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

200 Eagle Rise #15 Manchester VT 05254

MLS Number 4781194

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Monthly
  • Subdivision Eagle Rise

Winter Season In Vermont! Beautiful Eagle Rise home now available for Winter Rental. Great location with awesome views. Completely furnished. Enjoy all that Manchester and the Mountains have to offer for the Winter Season. Deck off the dining area offers great BBQ area and great views. Master bedroom ensuite. Bright first floor living room with flat screen tv. Downstairs living room offers sleeping for two on a pull out sofa. Nice dining area and a breakfast counter as well. Available for 3-5 months.

Listed by Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

2 Black Bear/Quarter Mile Stratton VT 05155

MLS Number 4780198

  • Rentals
  • Bedrooms 3
  • Bathroom 2
  • Lease Seasonal

Winter 19/2020 is coming fast! and its going to be awesome!!.. why wait any longer-- this is a perfect affordable cozy condo..and a Great location - Just a short distance from your front door or take the shuttle to Stratton Mountain Resort. These are the original classic Stratton Condos - a great skiing experience. Nicely decorated with mudroom entry, 3 bedrooms, sleeps 8+ comfortably. Easy open kitchen and living room in a cozy warm atmosphere. Easy Peasy.. why fuss elsewhere?

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

2357 Richville Manchester VT 05255

MLS Number 4777312

  • Rentals
  • Bedrooms 3
  • Bathroom 2
  • Lease Monthly

Charming three bedroom (sleeps 6) furnished quintessential Vermont Farmhouse. Available for 1-2 months for 2019-2020 Winter Season. Also available for Vermont 2020 Summer Festival Horse Show 4-6 weeks. This is a smoke free, no pet home...

Listed by Dan DeMasi and Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

99 Lake Pauline Ludlow VT 05149

MLS Number 4775283

  • Rentals
  • Bedrooms 2
  • Bathroom 1
  • Lease Seasonal

Winter seasonal rental available November 1, 2019 to April 30, 2020. Winter seasonal price $10,500 plus utility deposit $2,000 and security deposit $1,500. Super close to Okemo's Jackson Gore parking area 1.9 miles away. Perfect for those looking for an affordable rental and a convenient winter location. Two bedrooms, one bath, cozy living area with pellet stove. Galley kitchen. Easy to maintain and ready for the upcoming winter ski season at Okemo!

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

1226 East Ash Plymouth VT 05056

MLS Number 4775288

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Seasonal

Winter seasonal lease available beginning Nov. 1 to April 15, 2020. Fully appointed, tastefully decorated and furnished three bedroom, three bath condominium perfect situated between Okemo and Killington Mountains. $14000 plus utilities deposit $3000 and security deposit $1400 due prior to rental starting. Cozy living room with fireplace and lovely western views to capture sunsets. If you are looking to ski this winter at Okemo and Killington, come check out this condominium.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

F6 Cobble Ridge Winhall VT 05340

MLS Number 4773795

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Seasonal
  • Subdivision Piper Ridge

AVAILABLE FOR 2019/2020 SEASON. This Piper Ridge unit has stunning views. It has the perfect mudroom/entryway to store all your equipment and outerwear after the long day on the slopes. Inside is a newly renovated kitchen with marble counter-tops, all new stainless steel appliances breakfast bar with seating for 4. A large open living room with many windows to enjoy the mountain view , wood burning fireplace, flat screen TV. This is the perfect home for those who have a working vacation; this home provides a single office in the loft. The den has a queen sofa sleeper. This home has three full baths and an indoor hot tub. Large deck with grill for outdoor cooking. Bedroom setup is Master: King Bed, Bedroom: King Bed, Bedroom: 2 Twin beds, Loft: Twin Sofa Sleeper.Piper Ridge has a shuttle bus to the Stratton resort village, and a sports center clubhouse with indoor pool, gym, racquetball, and lounge. Less than 3 miles from Stratton and fully serviced via shuttle on all weekends and holidays during the winter ski season!

Listed by Christopher Cummings of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

166 Windy Mount Holly VT 05758

MLS Number 4772830

  • Rentals
  • Bedrooms 5
  • Bathroom 5
  • Lease Seasonal
  • Acreage 111

Winter seasonal available November 15, 2019 to April 15, 2020. Enjoy beautiful family-owned home on over 100 acres, minutes from Jackson Gore and Okemo. “Windy Hill” at the base of Salt Ash Mountain offers commanding views of Okemo and the Appalachian Trail in picturesque Mount Holly. Enjoy winter in a comfortable, family friendly 200-year- old restored farmhouse complete with antiques and modern amenities to make your vacation stay both charming and comfortable. Features: 5 bedrooms, 5 full baths, fully equipped chef's kitchen with restaurant grade gas range, Dacor double ovens, dining room that seats 10, living room with cable TV, wifi, indoor heated swimming pool room-great for yoga as well with views of surrounding mountains and fields. Gas grille, wrap around deck for spectacular sunsets of fields, forest and the Green Mountains. Enjoy hiking, cross country skiing, snowshoeing, tobogganing and sledding right on the 111 acres. Tenants must be swimmers. No fireplace. Tenant needs to be vetted by the landlord. 8 to 10 occupants. $5000 utility deposit plus $2000 security deposit.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

35 Sugar Bush Stratton VT 05155

MLS Number 4770782

  • Rentals
  • Bedrooms 5
  • Bathroom 5
  • Lease Seasonal

One Gorgeous Winter Retreat. Less than 5 minutes to the slopes and you are in complete luxury. A huge living room and Dining Room and Kitchen area..Wood burning Fireplace to make this cozy retreat warm and fun. 5 bedrooms (3 en suite), 4.5 bathrooms, game room- Ping Pong and Fusball.. Big deck and Hot tub and views of Stratton in Winter. For lots of fun and lots of friends. Definitely worth a look.

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.68% last updated on Dec 5, 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

Broker Reciprocity

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 December 8, 2019.