Search Guest Houses in Windsor

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Nov 28 - Nov 30
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Dec 19 - Dec 21
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Jan 16 - Jan 18

Guest Houses in Windsor

Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (345)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
$85 nightly
The price is $95
Nov 18 - Nov 19
Total with taxes and fees
The Central Downtown Inn & Suites
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (118)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
$122 nightly
The price is $130
Nov 19 - Nov 20
Total with taxes and fees
Blooming Inn
Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi
The Revival House

The Revival House

3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
"We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!"
United States
Mason
$150 nightly
The price is $168
Nov 18 - Nov 19
Total with taxes and fees
The Revival House
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (267)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$189 nightly
The price is $211
Nov 18 - Nov 19
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
Smart TV, Netflix, streaming services
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls
10.0 out of 10, Exceptional, (119)
"We had a great visit! Easy to access, clean and comfortable. The studio had everything we needed!Great host!"
United States
Marina G.
$131 nightly
The price is $146
Dec 3 - Dec 4
Total with taxes and fees
In town, newly remodeled studio with private balcony
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 19 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Windsor

Windsor Guest Houses information

Number of reviews
871
Accommodation
9 Guest Houses
Lowest Price
$95
Highest Price
$211

Frequently asked questions

What is the nightly rate for a guest house in Windsor?
Rates for Windsor guest houses vary, but travelers can find great-value prices from $95 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Windsor guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Windsor guest house and a B&B?
A guest house in Windsor is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

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