Search Guest Houses in Windsor

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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, (344)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
$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)
"The Revival House was very nice, the common areas are very well kept and will be even better once the little bar/restaurant area opens. As for the room, it was clean and spacious, though I could hear a great deal of my neighbors from any direction, but I suppose that's just what happens with an old house and noise generally died down by ten. Check-in and out were easy and the owners responded quickly if I sent them a text. I would probably stay again."
United States
Jaclyn
$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.
$188 nightly
The price is $210
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)
"Lovely apartment, perfect for a short getaway for city slickers. Close to town. The apartment was great, came well-equipped and everything was as described. The deck was lovely to spend a slow morning having breakfast. "
United States
Megan N.
$131 nightly
The price is $146
Nov 23 - Nov 24
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 3 days ago
Berkshire Mountain Lodge

Find out more about Windsor

Windsor Guest Houses information

Number of reviews
871
Accommodation
9 Guest Houses
Lowest Price
$95
Highest Price
$210

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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