Windsor holiday rentals

We found 298 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Windsor that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Windsor

Showing deals for:13 Nov - 20 Nov

Interior
Pool
.
Property grounds
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
AU$42,673
for 7 nights, 1 home
AU$6,096 per night
includes taxes & fees
Reading Farms Estate
Property grounds
Living area
Living area
Pool
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
AU$7,606
for 7 nights, 1 cabin
AU$1,087 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
spiral stairs lead up to master bedroom suite or down to den & laundry
Deck dining above the brook!
A cozy, welcoming place for all seasons
Lofted master suite with views to the night sky from the king bed
Exceptional
(75 reviews)

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

Woodstock

9% off
AU$3,584
for 7 nights, 1 chalet
AU$512 per night
includes taxes & fees
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Welcome to our Quechee Home!
Dining
Living area
Indoor Pool at the Quechee Club
Exceptional
(33 reviews)

6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont

White River Junction

8% off
AU$8,861
for 7 nights, 1 home
AU$1,266 per night
includes taxes & fees
6-Bedroom Peaceful and Private Retreat in Scenic Quechee, Vermont
Second master with ensuite bathroom
Living room and dining area with views of Ascutney Mountain
Kitchen  with soapstone counters, cherry wood floors, and walk-in food closet.
View from the deck
Exceptional
(42 reviews)

Exquisite Log Home with views near Woodstock, Vermont

Brownsville

15% off
AU$4,355
for 7 nights, 1 home
AU$622 per night
includes taxes & fees
Exquisite Log Home with views near Woodstock, Vermont
Stairs to the living area
Exterior
Main house garden
kitchen area
Exceptional
(115 reviews)

Woodstock Village Carriage House

Woodstock

8% off
AU$3,194
for 7 nights, 1 cottage
AU$456 per night
includes taxes & fees
Woodstock Village Carriage House
Living area
Dana Road House in October
King bed in master suite :)
patio, redwood hot tub in gazebo
Exceptional
(100 reviews)

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Woodstock

8% off
AU$4,296
for 7 nights, 1 home
AU$614 per night
includes taxes & fees
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
Property grounds
Property grounds
Terrace/patio
Living area
Exceptional
(9 reviews)

Classic Vermont Farmhouse in the Heart of Woodstock - close to skiing

Woodstock

17% off
AU$4,100
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
Classic Vermont Farmhouse in the Heart of Woodstock - close to skiing
Kitchen
Lake Pinneo Sunset
Corner unit next to lawn
Downstairs alternate view
Exceptional
(48 reviews)

Renovated Quechee Lakes Condo. Quechee Club Amenities! 15 mins Woodstock, VT!

Quechee

11% off
AU$3,045
for 7 nights, 1 apartment
AU$435 per night
includes taxes & fees
Renovated Quechee Lakes Condo. Quechee Club Amenities! 15 mins Woodstock, VT!
Full kitchen
Exterior
Interior
Dining area seats 8
Wonderful
(5 reviews)

2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area

Cavendish

16% off
AU$2,573
for 7 nights, 1 apartment
AU$368 per night
includes taxes & fees
2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area
Private kitchen
Property grounds
Interior
Interior
Exceptional
(18 reviews)

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Reading

8% off
AU$2,273
for 7 nights, 1 cottage
AU$325 per night
includes taxes & fees
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Dining
Living area
Room
Living area
Exceptional
(30 reviews)

Windfall @ Quechee Club VT: Cozy Updated Condo A/C, Fireplace -Ski -Golf -Renew

Quechee

8% off
AU$2,885
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Windfall @ Quechee Club VT: Cozy Updated Condo A/C, Fireplace -Ski -Golf -Renew
Cottage front
Deck with chiminea
Stairs to the 2nd floor
Living/Dining room with gas stove
Exceptional
(85 reviews)

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor

8% off
AU$2,223
for 7 nights, 1 cottage
AU$318 per night
includes taxes & fees
Cozy Historic Hilltop Cottage with Mount Ascutney View
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Windsor is ready to explore

The forests, mountains and countryside are the perfect backdrop to your holiday home in Windsor. Travellers to this scenic city praise the golfing, hiking and bird watching. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Windsor

Are you hoping to find attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Quechee State Park (11 mi / 17.7 km)
  • Upper Valley Aquatic Center (11.4 mi / 18.3 km)
  • Whaleback Mountain (13 mi / 20.9 km)
  • Sugarbush Farm (13.4 mi / 21.5 km)
  • Newport Golf Club (14.1 mi / 22.6 km)
  • Saskadena Six Ski Area (15 mi / 24.1 km)

Exploring the natural features in Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Windsor. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Mount Ascutney (4.2 mi / 6.8 km)
  • Quechee Gorge Bridge (10.9 mi / 17.6 km)
  • Marsh-Billings-Rockefeller National Historical Park (13.1 mi / 21.1 km)
  • Perkins Pond (14.4 mi / 23.2 km)
  • Mascoma Lake (15.7 mi / 25.3 km)
  • Echo Lake (15.8 mi / 25.4 km)

Travelling to and around Windsor

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 10.7 mi (17.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away.

If you'd prefer to travel by train, the main station serving the city is Windsor Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Windsor?
Cabins are the most popular style of holiday home in Windsor, according to our data. Even if you have something different in mind, Stayz has properties in many sizes and shapes. Take a look at our options to find your perfect Windsor pad.
How much does it cost to rent a holiday home in Windsor?
Season, property type and length of stay are some factors that can determine the price of a holiday home. Simply add your travel dates to find your ideal fit. From cosy country cottages to sprawling villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Windsor?
The average price for a holiday home by the beach in Windsor depends on when you're going and the type and size of property you're looking for. You can quickly and easily find prices on Stayz by entering your travel dates. Then use our handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.
What are popular home amenities in Windsor?
Some of the most popular home amenities people prefer in Windsor include tennis, a barbecue grill and a garden. Whether you're on the road with buddies, family or even pets, Stayz holiday properties include the best amenities for fun and relaxation with the people that matter most.
What are the top attractions for families in Windsor?
There's a ton of awesome things to do and see with the family in Windsor, including:
  • American Precision Museum
  • Maple Lanes
  • Mount Ascutney
How old do you have to be to rent a holiday home in Windsor?
It's advisable to check with the Windsor holiday property you're looking at on Stayz as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Windsor for?
The length of time you can rent a holiday home in Windsor is down to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With tons of creature comforts such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere perfect to call your home away from home in Windsor.