We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Windsor Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $301 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Windsor area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Windsor
    Sort by:
    Default
    The following rentals are within 25 kilometres of Windsor.
    The Farmhouse1 / 18
    (1)Excellent
    South Pomfret
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Secluded, Spectacular House with Mount Ascutney Vi1 / 20
    (4)Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    White River Junction
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Savage Hart Farm - a Sheep Farm with an Apartment1 / 12
    (1)Excellent
    White River Junction
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Washer
    • Grill
    • Mountain Views
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2014
    Modern, clean apartment with beautiful views. Quintessential New England! Fully equipped kitchen (and BBQ grill) made cooking in easy. Todd was a gracious host and most...
    See all reviews
    About this property
    On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the heart of New England. You'll find a retreat-type setting close to the center of the towns of Hanover, NH, and Norwich, VT in a bucolic locale even the locals talk about. Quechee is...
    View all property information
    Location Information
    White River Junction, Hartford 05001
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Hakuna Matata1 / 28
    (1)Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home one of the best Killington vacation rentals around - the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the...
    View all property information
    Location Information
    Bridgewater, Vermont 05035 4409
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Beauty & Privacy on 24 acres, sleeps 81 / 10
    (10)Very good
    Brownsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Patio
    • Parking
    • Balcony
    • Mountain Views
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Wonderful House in Brownsville, Vermont 1/4 mi to Ascutney Mountain Resort (hiking, biking, but skiing is closed) 12 miles to Woodstock, VT 30 minutes to Mount Okemo. 4 hours to Manhattan via Merrit Pkwy and I-91 3 hours to Boston The perfect vacation spot for leaf-peeping, or just kicking...
    View all property information
    Location Information
    Brownsville, Vermont 05037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Sunny mountainview home featuring a fireplace and spacious deck1 / 24
    (1)Average
    Brownsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Patio
    • Grill
    • Mountain Views
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2017
    My daughter and I went on a long weekend vacation to Vermont. We rented this home for 3 nights. The location of the home has gorgeous mountain views. The day we were to arrive...
    See all reviews
    About this property
    Retreat to your own hideaway in the woods of West Windsor, where views of mountains and valleys greet you through each bright window. Whether you choose to take in the scenery from the deck or warm up by the fireplace, this home is all about slowing down in the mountains. West Windsor Retreat is...
    View all property information
    Location Information
    Brownsville, Vermont 05089
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is a beautiful 3 bedroom, 2 bath with large family room and sleeps 10. In winter we are 4 minutes to skiing at the fabulous resort of Okemo/Jackson Gore. You ski, board, ice skate, snowmobile, snow shoe, cross country or go to the spa for a day of fun. At our house we have an outdoor hot...
    View all property information
    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Reading Farms Estate/ Vermont Luxury Rental1 / 53
    (4)Excellent
    Reading
    15 Bedrooms, 12 Bathrooms, Sleeps 44 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2015
    We just returned from our stay at Reading Farms and it was truly amazing, the chef cooked us a to die for meal and the staff did a firework show for us our last night that was...
    Reviewed 26 June 2014
    I had a lovely time at Reading Farms Estate over the Memorial Day weekend. The property is stunning, with sweeping views of the surrounding mountains and excellent service and...
    See all reviews
    About this property
    Reading Farms lies in the heart of Vermont. A completely private 400 acre estate. One of Vermont's most majestic properties has been held by the same owners for nearly 100 years. The secluded estate is conveniently located minutes from Woodstock Vermont and two of the best Vermont ski areas...
    View all property information
    Location Information
    Reading, Vermont 05062
    Holiday Rental House - 15 Bedrooms, 12 Bathrooms, Sleeps 44
    Make Enquiry
    Brownsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a burbling brook at the base of the hill. The historic converted early 1800's one room school house is filled with many antique furnishings. Hanging in the stairway are photographs...
    View all property information
    Location Information
    Brownsville, Vermont 05047
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Windsor rentals sent straight to your email!
    Get the List
    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winter, spring, summer and fall, there is always something to do and something to fall in love with at this cozy Vermont vacation home. Kids will love the rustic sturdy bunk beds and folks just love to relax in front of the fire, cozying up to a good book. There are many downhill and cross country...
    View all property information
    Location Information
    Bridgewater, Vermont 05035
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 2 full Bathrooms, Sleeps 6 adults with 2 sofa sleepers for children This house is 5 miles from Okemo skiing. Nearby are VAST snowmobile trails. There shuttle service from house to Okemo Mountain so you don't have to deal with parking. Killington Mt is 18 miles. Nearby snowmobile...
    View all property information
    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Proctorsville
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    • Mountain Views
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 1 Bathroom, Sleeps 6 has Sofa Bed for kids. This home is located 5 miles from Okemo Mountain. Okemo is a great family resort for skiing. If its snowmobile trails you are looking for the house is near VAST Trails. Also there is snowmobile rental about 1 mile away. There is a shuttle...
    View all property information
    Location Information
    Proctorsville, Vermont 05153
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Quechee
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Hot Tub
    • Wi-Fi
    • Shared Indoor Pool
    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome, this townhouse is located in one of the most beautiful 4 season areas of Vermont. You have many activities close by and great restaurants and shopping as well. If you enjoy golfing, lakes, pools and skiing the Quechee Club is in walking distance. Just a short drive from Dartmouth if you...
    View all property information
    Location Information
    Quechee, Hartford 05001
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 bedroom lake home on Crescent lake1 / 11
    (1)Excellent
    Newport, NH
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a quiet, pristine New Hampshire lake, this home and scenic surroundings provide a haven of rest for your vacation. Our private sandy beach sits on 510 feet of shoreline and invites you to enjoy carefree sunbathing and swimming in a safe, beautiful setting. Shade trees on the grounds...
    View all property information
    Location Information
    Newport, New Hampshire 03773
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nature have made this a favorite...
    View all property information
    Location Information
    Bridgewater, Vermont 05035
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Brownsville
    Studio, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Parking
    • Mountain Views
    • DVD Player
    • Washer
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The condominium lies on the West face of historical Ascutney Mt in the small town of Brownsville. The condominium consists of 3 bedrooms, 2 1/2 bathrooms, a small family rec room, living room, and dining area. A very comfy and warm atmosphere with access to a full service sports and fitness center....
    View all property information
    Location Information
    Brownsville, Vermont 05089
    Condo/Apartment - 3 Bathrooms, Sleeps 6
    Make Enquiry
    Grantham, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Private Indoor Pool
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forget all your troubles at this 3-bedroom, 2-bathroom tranquil Grantham condo. With enough room to accommodate 6 guests throughout 1,200 square feet of carefully appointed living space, this condo is a fantastic size and layout for families, friends or couples traveling together. From the spacious...
    View all property information
    Location Information
    Grantham, New Hampshire 03753
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Bridgewater
    4 Bedrooms, 3 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply known as 'The Cabin', this 5,000 S.F. home that is surrounded by ten private acres within brilliant wilderness, the majestic mountain range in your own backyard. Designed with the purpose of bringing people together, it perfect setting for hosting gatherings for friends, families and...
    View all property information
    Location Information
    Bridgewater, Vermont 05035
    Cabin Holiday Rental - 4 Bedrooms, 3 Bathrooms, Sleeps 24
    Make Enquiry
    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property includes 7 bedrooms (robes, bath amenities, tempurpedic beds, fireplaces, vable television, DVD and ensuite baths in all but 2), 8-person hot tub, dining for 24. Great for large groups or big families or specialb events. Warm weather Rustic Barn with bar can seat up to 115 guest...
    View all property information
    Location Information
    Cavendish, Vermont 05142
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 17
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Grantham, NH
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Parking
    • Wi-Fi
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very spacious 3 level stand alone condo. Inviting atmosphere for relaxation. Near West Cove beach at Eastman lake within walking distance. Great for swimming,canoeing,kayaking,sailing which can be rented through the South Cove activity center. 18 hole Championship Golf Course and thirteen tennis...
    View all property information
    Location Information
    Grantham, New Hampshire 03753
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy a beach view in VT! refreshing yourself in a lovely beach painting room. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for...
    View all property information
    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Brownsville
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Parking
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Travelers looking for a little peace and quiet in the forests of Vermont will adore this spacious, full-featured home away from home complete with a wood-burning fireplace, multiple living spaces, gorgeous mountain views, and room for up to 10 lucky guests making this home ideal for summertime...
    View all property information
    Location Information
    Brownsville, Vermont 05037
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cozy and comfortable room with the sun shines all day! It is an opened bright space with big windows all around. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road...
    View all property information
    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Cavendish
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is less then 10 minutes to the base of Okemo Mountain yet it's in a secluded quiet development. This spacious home has 4 bedrooms and 2 1/2 baths. There is plenty of seating in the kitchen and dining room. There are TV's int he family room as well as the master bedroom and one queen...
    View all property information
    Location Information
    Cavendish, Vermont 05142
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Perkinsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful bed and breakfast Vermont getaway! with 3 comfortable bedrooms available. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for biking,...
    View all property information
    Location Information
    Perkinsville, Vermont 05151
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • Grill
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will definitely love this classic, unique, beautiful and comfortable studio room. It's a great space for your vocation. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet...
    View all property information
    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in