Holiday rentals in Windsor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Farm stay in Plainfield

4.97 out of 5 average rating, 175 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. It is a daily work in progress, gardening and taking care of the chickens and sheep, so it is not perfect, but it is lively and ever-changing. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

25 Nov – 2 Dec

€ 157 per night
Guest favourite

Guest house in Hartland

4.96 out of 5 average rating, 158 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

10–17 Mar

€ 181 per night
Guest favourite

Flat in Springfield

4.9 out of 5 average rating, 221 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.

16–23 Apr

€ 107 per night

Popular amenities for Windsor holiday rentals

Stay near Windsor's top sights

Cornish-Windsor Covered Bridge28 locals recommend
Mt Ascutney State Park19 locals recommend
Harpoon Brewery Taproom and Beer Garden125 locals recommend
Windsor Station Restaurant & Barroom33 locals recommend
Pizza Chef15 locals recommend
Windsor Diner7 locals recommend

Other great holiday rentals in Windsor

Guest favourite

Guest suite in Hartford

4.92 out of 5 average rating, 309 reviews

Sunny Side Airbnb (dog friendly)

19–26 Apr

€ 115 per night
Guest favourite

Flat in Grantham

5.0 out of 5 average rating, 147 reviews

Dartmouth / Lake Sunapee Region

27 Nov – 4 Dec

€ 128 per night
Guest favourite

Tiny home in Hartland

4.95 out of 5 average rating, 144 reviews

Cabin on the Hill

29 Apr – 6 May

€ 94 per night
Guest favourite

Flat in Weathersfield

4.97 out of 5 average rating, 109 reviews

Cute VT Bungalow With 180 Degree View of NH

19–26 Jun

€ 180 per night
Guest favourite

Flat in Lebanon

4.91 out of 5 average rating, 517 reviews

Green Street Hideaway. Downtown Lebanon.

19–26 Apr

€ 112 per night
Guest favourite

Home in Plainfield

4.89 out of 5 average rating, 116 reviews

Historic Home on 17 acres of land. Go escape!

25 Mar – 1 Apr

€ 670 per night
Guest favourite

Home in West Windsor

4.98 out of 5 average rating, 127 reviews

Firewheel Hill: Private, contemporary house

28 Apr – 5 May

€ 269 per night
Guest favourite

Guest house in Woodstock

4.98 out of 5 average rating, 203 reviews

Cozy Little Spot (Self Check-in)

30 Jan – 6 Feb

€ 171 per night
Guest favourite

Home in West Windsor

4.96 out of 5 average rating, 50 reviews

Birdie's Nest Guesthouse

26 Jul – 2 Aug

€ 152 per night
Superhost

Home in Hartland

4.95 out of 5 average rating, 38 reviews

Cozy 1 bedroom home with private hot tub

22–29 Jul

€ 106 per night
Guest favourite

Home in Windsor

5.0 out of 5 average rating, 49 reviews

Modern custom home on a side of Mt Ascutney

11–18 Jan

€ 407 per night
Guest favourite

Cabin in Windsor

5.0 out of 5 average rating, 24 reviews

Charming Cabin in Central VT

14–21 Mar

€ 253 per night

Quick stats about holiday rentals in Windsor

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.7K reviews

Nightly prices starting at

€ 37 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Windsor