Our Southern Vermont Rentals

We specialize in seasonal and long term rentals and have a wide variety of rental properties in Southern Vermont covering the Ski Resort towns like Stratton, Bromley, and Magic as well as Manchester, Dorset and all of the surrounding towns. Coming to visit for the Manchester Summer Horse Show Festival, want to enjoy the spectacular fall foliage or want a winter getaway? Every season in Southern Vermont has something to offer and we would love to help you plan your stay here! Please contact us at any time with questions or a request to schedule a viewing.

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Cold Moon Farm

Jamaica VT

Jamaica, VT

Rental Price$50,000

Listing Number 7

  • Non-MLS Long-Term Rentals House,Winter Rental,Winter Seasonal
  • Lease winter seasonal
  • Bathroom 5
  • Maximum Occupants 19
  • Bedrooms 6

Come experience what Vermont has to offer! This 6 bedroom house is great for entertaining guests with a large open concept living room and kitchen. With three separate quarters there is enough space for everyone to stretch out and relax! You can enjoy sitting in the hot tub soaking up the view of the active farm and beautiful Vermont mountains. This house sleeps 17-19 people - in the left upstairs wing of the house has one bedroom with two twins, a full bath and another bedroom with a queen sized bed. Downstairs of the main house there is a game room with a ping pong table, pool table, skee ball and a gym. There are two bedrooms as well. One with two full beds and two twins with trundle as well as an attached full bath. The other bedroom has queen sized bed with an attached full bath. Upstairs of the main house offers two bedrooms each with an attached full bath. One bedroom has a queen sized bed and attached library suite with two twin pull outs. The other bedroom has king sized bed with an attached full bath. There is also an on-site caretaker so you will have help whenever needed. Life is good here on the farm!  PLEASE NOTE: This house is available December 1st - April 15th

Listed by Mary Kate Grey of TPW Stratton

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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8C Basswood Row Stratton VT 05155

MLS Number 4712210

  • Rentals
  • Bedrooms 4
  • Bathroom 4
  • Lease Seasonal
  • Subdivision Tree Tops

After a LONG GREAT day of skiing, who wants to drive 30 minutes to get home. SKI HOME!! You'd be here... Home... by now if this Tree Tops unit was yours this winter. Complete luxury. Gorgeous 4 bedroom, 4 bath. Plenty of room for large groups. Great big living room with huge stone fireplace and dining room to entertain. Gourmet kitchen and hot tub for apr├Ęs ski...Live a little... life is short! This Luxe "C" unit is top of the line - no expense spared. Come see it. New Snow Bowl lift is awesome. Don't miss out - be here for the fun this Winter!

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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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7 Balsam Stratton VT 05155

Stratton, VT7 Balsam

Rental Price$35,000

MLS Number 4773847

  • Rentals
  • Bedrooms 4
  • Bathroom 4
  • Lease Seasonal

2019-2020 Seasonal Rental, Fantastic 4BR/4BA Treetop townhome with direct trail access. Plenty of room in the Living, Dining and Kitchen area. Gather round the soaring stone fireplace or soak in the outdoor hot tub. Make Stratton Vermont your home away from home this winter!

Listed by Karin Hardy of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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165 High Meadow Stratton VT 05155

MLS Number 4769313

  • Rentals
  • Bedrooms 4
  • Bathroom 5
  • Lease Seasonal

Gorgeous up to date Chalet with a small great view of the peak of the peak of Stratton in the wonderful High Meadows neighborhood. less than 5 minutes to the slopes. No dealing with slowpokes trolling up the access rd who don't know how to drive in Snow.. you'd already BE THERE. Great living room with wood fireplace and deck for outdoor grilling. A huge downstairs living room area with wet bar. Even a Baby Grand to listen to your "little Angels" "recitals" and rendition of "Chopstix"! And 4 TV'S throughout for entertaining. Super kitchen for all you Chefs! 4 really nice bedrooms and drive in garage so once you're home.. you're home! This won't last.

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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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12 Sap Bucket Winhall VT 05340

MLS Number 4662846

  • Rentals
  • Bedrooms 4
  • Bathroom 3
  • Lease Seasonal
  • Subdivision Forest Farms

A warm inviting home with open floor plan. Stone fireplace in living room with cathedral ceiling. Four bedrooms, 3 large baths and Master with whirlpool tub and sauna and shower and king sized bed . Guest bedroom with queen bed, separate bath and shower. Deck, grill, views of Stratton, hot tub in solarium. Two car attached garage and laundry. Great location -2 miles to Sun Bowl.. 5 minutes to base lodge and go the back way up by SMS and avoid any early am traffic to grab first chair.

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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634 Equinox on the Battenkill Manchester VT 05254

MLS Number 4664909

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Seasonal

Winter Rental available for 2019/20 Season. This Equinox on the Battenkill unit comes furnished and sleeps 12. The main level features the kitchen and dining area and a spacious living room with a wood burning fireplace perfect for snowy winter days. Den with TV and plenty of seating. Full bathroom on main floor. Second floor has two large bedrooms with vaulted ceilings and 2 full bathrooms. Lower level offers a large family/media room, bunk room, and laundry room. Complex amenities include paddle tennis court. Close proximity to skiing Bromley and Stratton, located in Manchester village, down the hill from the Equinox Hotel.

Listed by Chrissy Carroccio of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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194 Birch Jamaica VT 05343

Jamaica, VT194 Birch Lane

Rental Price$15,000

MLS Number 4781489

  • Rentals
  • Bedrooms 2
  • Bathroom 2
  • Lease Seasonal

This updated chalet is hard to beat. The home has been updated with a very creative and eclectic style. There are two bedrooms, two bathrooms and also a very ingenious bunk room. There is room for 8 people to stay comfortably. The kitchen has been upgraded to a modern "chef's kitchen" with new appliances and fabulous fixtures. All of this comes at a reasonable price and with a location just 10 minutes from the Stratton Access Road.

Listed by Peggy O'Neill of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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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4591 Vt Rt 30 Jamaica VT 05343

MLS Number 4632233

  • Rentals
  • Bedrooms 4
  • Bathroom 2
  • Lease Seasonal

This is a delightful Winter retreat. After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 7 minutes from Stratton access Rd. Upstairs there are 3 bedrooms, kitchen, and living room with wood burning fireplace. Downstairs can be its own 1 bedroom unit with a splendid separate kitchen and living room space. If you want a nice, easy, comfortable winter for you and your family and friends... very close to Mountains... this is the house for you. At this price, it's a steal. Utilities and HEAT, except electric are included in this great price.

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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Jamaica4BedroomLogCabin

Jamaica VT 05343

Jamaica, VT

Rental Price$12,500

Listing Number wfbJamaica

  • Non-MLS Long-Term Rentals
  • Lease winter seasonal
  • Bedrooms 4
  • Bathroom 2

This private log cabin is located in a quiet setting and enjoys the luxuries to make your winter season a great one; including a washer / dryer, wood stove, BBQ grill, flat screen television, and fully equipped kitchen. All of this on a private property in close proximity to the ski resorts! This cabin is truly cozy, warm and fun for a family and friends to enjoy in all seasons... Summer, Fall and Winter. The owner is amenable to discuss variable lengths of stay and rates will be provided accordingly. Read: flexible and negotiable... and motivated!

Listed by Wilkie Bushby of TPW Stratton

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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320a Keith Hill Londonderry VT 05343

MLS Number 4605556

  • Rentals
  • Bedrooms 2
  • Bathroom 2
  • Lease Seasonal

Available for Winter Season '18-'19 from 11/15/18 to 4/14/19 This great 2 Bedroom 2 Bathroom home is located in a private setting. Single floor living. Apartment below is also occupied. Very private back deck with wooded view. Features a 1 car attached garage and extra parking in driveway. Very affordable and efficient winter seasonal rental for skiing close to Bromley, Stratton, Okemo, and just minutes from Magic Mountain. Fully equipped kitchen and home to suit all your needs! Come take a tour and see for yourself. Can't beat this price and location.

Listed by Wilkie Bushby of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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597 Winhall Station Londonderry VT 05155

MLS Number 4745630

  • Rentals
  • Bedrooms 5
  • Bathroom 4
  • Lease Seasonal

Why pay 45k to be up on Stratton when you can pay far less - like 15k ALL IN! Have great accommodations and be 4 miles to the Stratton access road and close to Magic too! Best of all worlds. 5 bedrooms - sleeps 8 in beds and 2 pullouts allow for more. Fantastic fields to play in and wonderful views as well. After a great day of skiing, get away from the hub bub and retreat and relax. No neighbors to worry about... frolic free!

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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Classic Jamaica Farmhouse

Jamaica VT

Jamaica, VT

Rental Price$12,000

Listing Number 84

  • Non-MLS Long-Term Rentals Winter Seasonal
  • Lease winter seasonal
  • Bedrooms 4
  • Bathroom 2
  • Half Baths 1

Classic farmhouse in Jamaica Village! This 4 bedroom 2.5 bathroom home is located 10 minutes from Stratton Access Road. Cozy up to the wood stove after a long day on the slopes. Entertain in the large sunlit dining room. This house is very welcoming and ready for tenants for this winter season. The main level offers a mud room entry with living room, den, kitchen, spacious dining room, a bathroom with a shower and second full bathroom with tub. Upstairs has a bedroom with a queen size bed, another half bathroom, one bedroom with two twins, a room with a full size bed and a twin, and another bedroom with a twin daybed. Three bedrooms upstairs feature private hand basins and ceiling fans. Available for seasonal rental from November 15 through April 15. Utilities not included.

Listed by Mary Kate Grey of TPW Stratton

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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142 Sweet Hollow Manchester VT 05254

MLS Number 4762493

  • Rentals
  • Bedrooms 3
  • Bathroom 3
  • Lease Monthly

Available Dates 7/2/2019 - 8/05/2019 1/03/2019 - 5/30/2019 3bedroom 2 1/2 bath home located in Historic Manchester Vermont. Come enjoy luxurious living within the gorgeous Southern Vermont Setting. Home is close to downtown actives and entertainment. Manchester is also a short drive to Stratton, Magic & Bromley Mountain Resorts.

Listed by Elliott Nachwalter and Dan DeMasi of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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212 Ormsby Hill Manchester VT 05254

MLS Number 4778708

  • Rentals
  • Bedrooms 5
  • Bathroom 5
  • Lease Monthly

**PRICE DROP! Now available for $5,500.00 per month... This is where you want to spend the Winter Season. Located in the Village at Ormsby Hill, this 5 bedroom, 5 bath spectacular home with vaulted ceilings and lots of room for large groups. Master suite on the main floor along with a formal dining room and breakfast nook. Two guest bedrooms ensuite on the upper level. Two guest bedrooms ensuite on the lower level along with the den. Spectacular views abound of the Green Mountain National Forest. Conveniently located for all that Manchester and the Mountains have to offer.

Listed by Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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3343 Main Manchester VT 05255

MLS Number 4754710

  • Rentals
  • Bedrooms 4
  • Bathroom 2
  • Lease Monthly

Available July 15th 2019 Authentic Restored Barn Home in a private setting now available for rent in the heart of historic Manchester, VT. This four bedroom, two bath Manchester Village country home boasts beautiful mountain views, and a large yard. Located just minutes to area entertainment, shopping and dining. Come stay the summer and enjoy all that Manchester & Southern Vermont have to offer.

Listed by Elliott Nachwalter and Dan DeMasi of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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

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 October 19, 2019.

 
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 October 19, 2019.