Williamson Group logo

Search Homes

Vacation Rentals in the Woodstock Area

Browse currently available vacation rentals in the Woodstock region of Vermont. If you have any questions about a specific vacation rental property please contact Williamson Group Sotheby’s International Realty.

Search Smarter - Create an account to save your favorite vacation rental listings and to receive email notifications when similar listings become available. If you don't see what you're looking for, you may want to try a custom search.

Summer/Fall Rental South Pomfret VT

Contact For Address South Pomfret VT 05067
For Rent

Listing Number X19319226

  • Non-MLS Vacation Rentals
  • Summer Rental
  • Date Available 06/15/2022
  • Maximum Occupants 6
  • Bedrooms 3

Nestled in the Pomfret valley, this beautiful farmhouse is available mid-June to the end of October.   3 bedroom, 2 1/2 bath home with a lovely and tasteful interior design providing guests a comfortable and relaxing experience.  Renovated and fresh with thoughtful touches, bright and light filled.  Spacious updated kitchen, living room with fireplace, dining room and cozy TV room with Smart TV on the first floor.  Primary bedroom and bath along with two additional bedrooms, shared and bath and laundry on the second floor.  Porch with table and chairs, grill, off street parking, mudroom entry with half bath.  Walk to Teagos for morning coffee, a sandwich at lunch, enjoy a performance at the Grange theater next door or nearby take a class at Artistree, view an art exhibit or sit up on the hill for an outdoor evening summer concert, jump on your bike or hike Suicide Six.  The village of Woodstock is @ 3 miles so easy to take enjoy shopping, dining, Billings Farm or golf, tennis, exercise workout and spa at The Woodstock Inn.  This property offers so much and will delight creating memories of a Vermont vacation.  WiFi, all internet access, no cable. Rent includes all utilities.  Security deposit and cleaning fee required.  Minimum one month.  No pets please.  No smoking.  Contact Williamson Group Sotheby's International Realty to schedule a showing of this exceptional property or for additional information.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

4 BR 4.5 BA Summer Rental Hartland VT

Contact for Address Hartland VT
For Rent

Listing Number X96561789

  • Non-MLS Vacation Rentals
  • Bathroom 4
  • Bedrooms 4

4 BR with 4.5 BA modern colonial farmhouse beautifully built and meticulously maintained will be the perfect spot to enjoy summer in Vermont.  Located on the Woodstock/Hartland town line, the house sits on 11 quiet and private acres only a short drive to Woodstock.   Large kitchen with sunroom, dining room, living room, master bedroom and bath, comfortable den on main level.  Bonus TV room over 2 car garage.  Spacious interior comfortably furnished with room for all to relax and settle in.  2 decks, patio, pond, yard with landscaped grounds and surrounding trees including a small screened in cabin in the woods.  $7,500.00/month including all utilities and WiFi.  No smoking.  A small dog may be considered in special cases with pet deposit and additional cleaning fee. The property is available for rent June, July and August.  Minimum 2 months.  Max occupancy 6 people. Security deposit, cleaning fee and references required. Please contact Williamson Group, Sotheby's International Realty with questions or to schedule a showing.  

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

Woodstock Village Seasonal Rental 3BR 2 1/2 BA

Contact For Address Woodstock VT
For Rent

Listing Number X22238609

  • Non-MLS Vacation Rentals
  • Date Available 05/01/2022
  • Bathroom 3
  • Maximum Occupants 6
  • Bedrooms 3

A wonderful opportunity to spend the summer or longer in the historic village of Woodstock, considered one of the prettiest towns in America.  Set on the banks of the Ottauquechee River, you will enjoy the soothing sound of the river and the cool breezes in this 3 bedroom, 2 1/2 bath village cape.  On the first floor it is furnished comfortably with an open kitchen living and dining room space and 1/2 bath, along with master bedroom, private bath and library.  There are 2 working fireplaces for chilly fall evenings.  On the second floor there are 2 additional bedrooms, an office/sitting area and a bathroom with a jacuzzi bathtub.  Exceptional stone work in the back with stone pathways and a stone terrace with views of a covered bridge, a lovely spot for dining outdoors or just relaxing by the river.  You can nap or read in the hammock or on the covered porch off the living room, enjoy the beautiful plantings and gardens that the owners have lovingly created from a private bench.  Parking for 2 cars.  All utilities included.  WiFi access for remote work, along with a printer.  There is a sauna in the lower level and a small charcoal grill in the back.  A pet may be considered in special cases with deposit.  Available May through October with winter availability December and January.  Multiple months preferred.   No smoking.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

4 BR Blake Hill Condo-Woodstock

Contact for Address Woodstock VT
For Rent

Listing Number X34824273

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Bedrooms 4

Desirable Blake Hill Condo available for rent beginning mid-October.  Located in Woodstock with easy travel proximity to Killington, Okemo and Suicide Six and access to I-89 for day trips to Stowe or Sugarbush.  This is an immaculate end unit, 4 bedroom three and a half bath, furnished comfortably and well appointed condo.  Multi level, efficient space, natural light, fireplace, open kitchen, living, and dining room.  Country hillside views from the interior and deck in a quiet setting just minutes from the village.  Pets with reference, deposit and additional cleaning fee may be considered in special cases.  No smoking.    Minimum one month, seasonal stay welcome.  Cable/internet available in the unit with installation and removal to be arranged by tenant at their expense.  Tenant pays heat, electric and cable/internet.  Condo is available for long term upon request.   1-2 months $6,500/month plus utilities..  3-4 months $5,500/month plus utilities.  Long term $3,500/month plus utilities.  Contact Williamson Group Sotheby's International Realty for additional information or to schedule a showing.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

5 BR Woodstock Home Seasonal Rental

Contact for Address Woodstock VT 05091
For Rent

Listing Number X32926093

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Maximum Occupants 8
  • Bedrooms 5

Wonderful 5 bedroom, 2 1/2 bath home available for seasonal rentals, up to 30 days.  Great room with cathedral ceiling open to kitchen, wood floors, natural light, spacious and comfortable for gathering with friends and family.  Radiant floor heating in kitchen and great room.  Short drive to the village Green, shopping, dining and services.  X-Country ski trails and Woodstock Athletic Club nearby.  10 minutes to Suicide Six.  No smoking.  Pets may be considered.  Maximum occupancy 8 people; parking limited for 2 cars

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

Woodstock 3BR Condo

Contact For Address Woodstock VT
For Rent

Listing Number X22493088

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Property Name Woodstock 3BR Condo
  • Bedrooms 3

Nicely appointed condo in Woodstock, VT offers a perfect balance of quiet and convenience. Just a short walk to the village, the three bedroom, three bath unit with fireplace, attached garage and deck is comfortably furnished, equipped for short term vacation rental. The unit offers privacy with nice views of the hillside. This is a wonderful opportunity in any season. No pets and no smoking. 1-3 months, $5600/month.  Longer term rental, $4500/month plus utilities.  Available November 2022.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

2 BR 2 BA Village Home,Monthly and Seasonal Rental

Contact for Address Woodstock VT 05091
For Rent

Listing Number X81807429

  • Non-MLS Vacation Rentals
  • Date Available 01/01/2022
  • Bathroom 2
  • Bedrooms 2

2 BR 2 BA cozy village home available for seasonal rental.  Nicely furnished and fully equipped with a guest's comfort in mind. All village amenities and activities walking distance from the back door.  Suicide Six, the Ski touring center, and Woodstock Athletic Club are minutes.  Close access to hiking, walking and snowshoeing from the house.  Maximum 2 cars with 2 off-street parking spots for tenant's use.  Winter rental season must have snow tires and AWD.   Arrive, park, relax and enjoy!     Available October 1, 2022. Seasonal fall rates apply.  Longer term pricing available upon request.   All utilities included.  Security deposit and final cleaning fee and bi-weekly cleaning required.  Pets may be considered in very select cases with references provided, additional cleaning fee and deposit.   No smoking.  Contact Williamson Group, Sotheby's International Realty to schedule a showing or for questions.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

3 BR Log Home

Contact for Address Woodstock VT 05091
For Rent

Listing Number X45111486

  • Non-MLS Vacation Rentals
  • Bathroom 2
  • Property Name 3 BR Log Home
  • Maximum Occupants 6
  • Bedrooms 3

Nestled on a bucolic hillside just 3 miles north of downtown Woodstock, this inviting, bright home is a magical place to gather. It's truly the perfect place to recharge after a day of skiing and exploring! The clean, well-maintained vacation rental offers 3 bedrooms, 2 bathrooms, and accommodations for 6. From here you're a few miles from the sites, shops, and museums of this classic New England town, 8 minutes from Suicide Six Downhill Ski Area, and 10 minutes from the Woodstock Country Club.  Unfortunately there is no summer availability at this time, but the cabin will be available agin in the fall and winter of 2021.  No smoking.  Pets may be considered in special cases.  Contact Williamson Group Sotheby's International Realty for more information.  

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

2 BR Duplex Woodstock Village

Contact for Address Woodstock VT 05091
For Rent

Listing Number X92639010

  • Non-MLS Vacation Rentals
  • Village Woodstock
  • Date Available 12/15/2021
  • Bathroom 2
  • Bedrooms 2

Renovated duplex with 2 BR and 1 1/2 baths located in the Woodstock village, walking distance to all amenities.  Front porch, side yard, back porch, off street parking, wood floors, bright with natural light, open living and dining room space, pellet stove, farmhouse kitchen, large utility room with washing machine and dryer, bedrooms and full bath on second floor.  Third floor has a large open finished room perfect for a yoga studio, office or project space.  Comfortably furnished to relax and disconnect.  Small dogs may be considered in special cases.  Tenant pays heat.  All other utility expenses and internet included. No smoking. Available now.  Contact Williamson Group, Sotheby's International Realty for questions or to schedule a showing.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

Woodstock Vermont Village Rental

Contact for Address Woodstock VT 05091
For Rent

Listing Number X34341545

  • Non-MLS Vacation Rentals
  • Date Available 06/01/2022
  • Bathroom 3
  • Maximum Occupants 6
  • Bedrooms 3

Wonderful village property available for short term vacation rental.  One bedroom, one bath bright and airy with great natural light, hard wood floors, river view.  First floor living primary bedroom and bath, river room with dining table and sitting area for reading or watching a movie or a favorite show, fireplace, updated kitchen,  a most soothing and inviting interior.  Back deck with river view, privacy and beautiful sloping yard to the the water's edge.  Convenient and excellent village location walking to all shops, restaurants, morning coffee, post office, errands and all activities and amenities the village has to offer.  Access to trails close by.  No pets.  No smoking.  Available May to October, minimum one month, 2-3 months preferred.  Maximum occupancy 2 people.  Contact Williamson Group Sotheby's International Realty for questions or to schedule a showing of this special village rental.

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

2 BR 2 BA Summer/Fall Rental

Contact For Address South Pomfret VT 05067
For Rent

Listing Number X68626701

  • Non-MLS Vacation Rentals
  • Date Available 05/15/2022
  • Bathroom 2
  • Maximum Occupants 4
  • Bedrooms 2

A charming cottage-style home located in the beautiful Pomfret valley, with views of Suicide Six and just a 5-minute drive to historic Woodstock.  A true Vermont experience awaits in this cozy and comfortably furnished 2-bedroom, 2-bath rental property.  Living Room with electric fireplace for chilly fall evenings,  Twin Bedroom with full Bath, and large Kitchen are on the Main Floor.  The sunny Dining Room opens via glass doors to a deck and patio in the private backyard.   The Mudroom and Laundry are on the finished Lower Level.  Guests comfortable using stairs will find the Queen Master Bedroom with adjoining full Bath.  Dressing Room and snug Reading Nook on the Second Floor.  Quiet but vibrant South Pomfret has a lot to offer:  art exhibits and classes at Artistree, the Grange Theatre, Appalachian Trail, and Teago Country Store with morning coffee, groceries and meals to go are within walking distance.  Stage Road itself is the area's most popular cycling route from Woodstock north.    Utilities (including wide-screenTV and WiFi) are covered (up to $100.00 on monthly electric charges); parking for 2 or more vehicles; no smoking; pets may be considered.  , tenant pays electric over $100.00. WiFi.   Available mid-May through mid-October.  Contact Williamson Group, Sotheby's International Realty to schedule a showing of this delightful rental or with questions. 

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

3BR Village Home

Contact for Address Woodstock VT 05091
For Rent

Listing Number X47836869

  • Non-MLS Vacation Rentals
  • Date Available 11/15/2020
  • Property Name 3BR Village Home
  • Bedrooms 3
  • Listing Type Seasonal

Antique craftsman style home with 3 BR, 1 1/2 BA furnished available October 1 to November 15, 2022.  Convenient location walking distance to village amenities.  Home has charming period feel with updated kitchen, wood floors, front porch, small yard, off street parking.  Tenant pays oil heat, electric and water.  Basic Internet, trash and recycling, plowing and lawn care included.  Upgrade to cable service available at Tenant's expense.  First and last month's rent plus security deposit equal to month's rent required.  Pets may be considered on a case by case basis with pet deposit.  No smoking.  Contact Williamson Group Sotheby's International Realty for questions or to schedule a showing.  

Listed by Emma Schmell of Williamson Group Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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

Broker Reciprocity

Copyright 2022 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 June 30, 2022.