Book Bed and Breakfast in Windsor

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Featured B&B in Windsor

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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.

Hotel Options in Windsor

    Life House Berkshires

    Life House Berkshires

    194 Pittsfield Rd, Lenox, MA
    The price is $115 per night from May 4 to May 5
    $115
    includes taxes & fees
    $103 per night
    May 4 - May 5
    9/10 Wonderful! (573 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

    190 Meadow Street, South Lee, MA
    The price is $134 per night from May 14 to May 15
    $134
    includes taxes & fees
    $120 per night
    May 14 - May 15
    9/10 Wonderful! (627 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $120 per night from May 4 to May 5
    $120
    includes taxes & fees
    $107 per night
    May 4 - May 5
    9/10 Wonderful! (1,001 reviews)

Bed and Breakfast

Book a bed and breakfast in Windsor
A romantic getaway awaits when you book a bed and breakfast in Windsor. The beauty of renting a B&B is that each one is unique. A farm B&B is cozy and rustic, while a luxury B&B provides top-of-the-line luxuries, including in-room jet tubs and thousand thread-count sheets. And let’s not forget the most important part of its name…breakfast! Bed & breakfasts are famous for putting out a great spread each morning. Fill your plate with fluffy pancakes with maple syrup, hot eggs right from the pan, and a cup of hot coffee to help get you ready for the rest of your day.

All are welcome at Windsor bed n breakfasts
Some cheap accommodations are designed to simply give travelers a roof overhead and a comfortable bed to sleep on between adventures or business meetings. This definitely isn’t the case with a bed and breakfast (also known as a breakfast inn). The right B&B doesn’t just host your vacation to Windsor, it becomes part of it. In many cases, travelers get to know the manager of the B&B, as well as mingle with other guests. Many B&Bs also arrange activities for guests, such as hikes in the area, bird watching outings, or fun game nights. 

B&B hotels have a reputation as a romantic retreat for couples. However, B&Bs are actually for all sorts of travelers. Book one with a parent, child, or your favorite travel buddy. Want to take your fur child on your adventure to Windsor? A quick search through Orbitz will bring up pet-friendly B&B options so your best friend can come along.

Windsor B&B essential information

Accommodation
24 B&B
Lowest Price
$115
Highest Price
$438
Popular accommodation
The Cornell Inn, Lenox & The Berkshires, Lakehouse Inn, Shaker Mill Inn, Chambery Inn, The Trail in Adams - Berkshires’ Art Hotel, 33 Main, Brook Farm Inn, Devonfield Inn B&B, Whistler's Inn Bed & Breakfast