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.

Holiday Rentals in Windsor

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €258 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 12
    Windsor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection

    The following rentals are within 25 kilometers of Windsor, Vermont.

    1 / 20
    5 of 5 bubbles (1) Excellent
    Reading
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 25
    Hanover, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 21
    4.5 of 5 bubbles (4) Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful contemporary mountain home in Vermont sitting in 150 acres of private land. Borders a State Park with beautiful trails and an 80 ft Cascade. 5 Bedrooms, sleeps up to 12. This sprawling home features a large kitchen, separate dining room, spacious living room with stone fireplace and... View all property information
    Location Information
    Perkinsville, Vermont 05151
    4 of 5 bubbles Reviewed 29 March 2016
    Overall the house is a very good rental option. It is really beautiful inside and outside and has beautiful surroundings. All rooms are really spacious and have comfortable...
    4 of 5 bubbles Reviewed 10 September 2015
    Very spacious home and great yard with lots to do..hiking trails close, swimming pool and tennis courts/basketball hoop and pool table inside. Something for everyone. The house...
    See all reviews
    1 / 22
    4.5 of 5 bubbles (6) Very good
    Grantham, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Shared Indoor Pool
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Skiing: Property Is...
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Eastman Four Season Resort in Mount Sunapee / Dartmouth area.<BR>3 bedroom/3 bath townhouse available for short or long term vacation rental. <BR>Sleeps 9! <BR>Eastman is a unique resort community that offers a pristine mountain lake and unaffected natural beauty, combined with the convenience of... View all property information
    Location Information
    Grantham, New Hampshire 03753
    5 of 5 bubbles Reviewed 2 August 2016
    My family has actually had the good fortune to rent this property in summer and winter. Since we stayed longer during our ski holidays I know it best then, but it's great any...
    5 of 5 bubbles Reviewed 31 May 2016
    >>>> We spent a very enjoyable July vacation at this charming lake home with our two children and my sisters family of 4'. The house was charming, clean and comfortable...
    See all reviews
    1 / 10
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    1 / 10
    4.5 of 5 bubbles (10) Very good
    Brownsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Central Heating
    • Satellite TV
    • Washer
    • Balcony
    • Patio
    • Mountain Views
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Brownsville, Vermont 05037
    1 / 28
    4 of 5 bubbles (1) Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-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 4409
    1 / 16
    Sunapee, NH
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is a MONTHLY rental only. There is a 2 MONTH minimum requirement. Please see the rates section below for more details. Spacious fully furnished 3,000 sf luxurious condo in a highly desirable condominium community four miles from Mount Sunapee Ski Resort with Fall, Winter, and Spring Lake... View all property information
    Location Information
    Sunapee, New Hampshire 03782
    1 / 18
    Grantham, NH
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Internet Access
    • Parking
    • Central Heating
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the Fall colors, Dartmouth football games, Sunapee ski weekends, and all that this beautiful region has to offer. 2BR, 2BA lakefront condo in Eastman, a planned recreational community located in the NH Upper Valley area. This condo was completely renovated in 2015 and features bamboo... View all property information
    Location Information
    Grantham, New Hampshire 03753
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 13
    White River Junction
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Mountain Views
    • Parking
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    1 / 32
    Sunapee, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Parking
    • Waterfront
    • Washer
    • Internet Access
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You’ll feel like you’re vacationing inside the pages of DWELL magazine in this brand new three/four bedroom lakefront house designed by a prominent Boston architect. Charming Kezar Lake, dotted with old farmhouses and inns, is a well-kept secret in the area. Old-fashioned Vernondale General Store,... View all property information
    Location Information
    Sunapee, New Hampshire 03260
    1 / 27
    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • Hot Tub
    • Mountain Views
    • Skiing: Property Is...
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 12
    5 of 5 bubbles (1) Excellent
    Newport, NH
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 53
    5 of 5 bubbles (4) Excellent
    Reading
    15 Bedrooms, 12 Bathrooms, Sleeps 44 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor...
    • Mountain Views
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    5 of 5 bubbles 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...
    5 of 5 bubbles 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
    1 / 12
    5 of 5 bubbles (1) Excellent
    White River Junction
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Grill
    • Mountain Views
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    5 of 5 bubbles 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
    1 / 34
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    1 / 17
    Quechee
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is...
    • Central Heating
    • Hot Tub
    • Wi-Fi
    • Shared Indoor Pool
    • Satellite TV
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 32
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Housekeeping...
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    1 / 24
    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bridgewater, Vermont 05035
    Get the List
    1 / 15
    Brownsville
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Parking
    • Mountain Views
    • DVD Player
    • Washer
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 24
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bridgewater, Vermont 05035
    1 / 24
    Grantham, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Private Indoor Pool
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Forget all your troubles at this 3-bedroom, 2-bathroom tranquil Grantham condo, which comfortably sleeps 6. From the spacious back deck, enjoy lakefront views and lush green pines before beginning a kayaking, biking, fishing or golfing adventure! You’ll know you made the right choice upon your... View all property information
    Location Information
    Grantham, New Hampshire 03753
    1 / 42
    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Kerwin House: After a long day on the slopes relax in your private indoor hot tub. Amazing single family home offers a huge open floor plan. This spectacular home has a large dining area with seating for 10 and a spacious kitchen fully equipped for your cooking needs. The living room has ample... View all property information
    Location Information
    Bridgewater, Vermont 05035
    1 / 51
    Perkinsville
    Private Room, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Mountain Views
    • Housekeeping...
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    1 / 20
    Bridgewater
    4 Bedrooms, 3 Bathrooms, Sleeps 24 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Skiing: Property Is...
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 12
    Brownsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 34
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Housekeeping...
    • Washer
    • Grill
    • Mountain Views
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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