Compare Inns in Windsor

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Featured Inns in Windsor

Apple Tree Inn

Apple Tree Inn

3 out of 5
10 Richmond Mountain Rd, Lenox, MA
$184 nightly
The price is $206 total per night
$206 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of Apple Tree Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and express check-out. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include a terrace, a garden, and a picnic area.
Pool
Breakfast included
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 out of 5
910 Cold Spring Road, Williamstown, MA
$119 nightly
The price is $133 total per night
$133 total
Oct 6 - Oct 7
Total with taxes and fees
1896 House Country Inn & Motels features free WiFi in public areas, conference space, and a business center. Free parking is included with your stay. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include a computer station, a terrace, and wedding services.
Pet friendly
Parking included
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street, Lenox, MA
Guests of Kemble Inn enjoy free WiFi in public areas, a hot tub, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with luggage storage and concierge services. Other amenities at this boutique inn include coffee/tea in a common area, a library, and free newspapers.
Hot Tub
Breakfast included
The Kemble Berkshires

The Kemble Berkshires

2 out of 5
2 Kemble St, Lenox, MA
Guests staying at The Kemble Berkshires enjoy free WiFi in public areas, a terrace, and a garden. If you decide to drive, there's free parking. This inn also has barbecue grills.
Parking included
Free WiFi
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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

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $86 nightly
    The price is $96 total per night from Nov 2 to Nov 3
    $96 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (668 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
    $129 nightly
    The price is $144 total per night from Nov 2 to Nov 3
    $144 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (741 reviews)

Inns

Find a great Windsor inn
If you’re on the lookout for a place to stay in Windsor that sports special touches and décor but is less costly than a bed and breakfast, rent a room at an inn. Whether you’re staying for a day, a week or a month, Orbitz has a great selection of super-comfy Windsor inns to choose from.

Pick the right inn for you
The most popular hotel inns in Windsor merge the convenience of an inn with many of the standard features of a hotel. Think pools and gyms, without the hefty price tag.

You’ll find Windsor inns are located in all sort of convenient neighborhoods, making them a great option for those traveling on four wheels. They can also offer a tasty breakfast and hearty dinner, saving you the time and effort it would take to find good eats in a new place. 

If you want a space filled with loads of personality and a good helping of hospitality to boot, look out for historic inns. Privately owned with an exclusive number of rooms, you’ll receive a more personalized stay, much like a boutique hotel. No matter what type of inn you choose, you’re sure to enjoy unique experiences you won’t find anywhere else.

Windsor Inns essential information

Accommodation
4 Inns
Lowest Price
$96
Highest Price
$206
Popular accommodation
Apple Tree Inn, 1896 House Country Inn & Motels, Kemble Inn, The Kemble Berkshires

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