Compare Cheshire Motels

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Featured Cheshire Motels

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Nov 23 - Nov 24
Total with taxes and fees
Howard Johnson by Wyndham Lenox features an outdoor pool, free WiFi in public areas, and coffee in a common area. There's free parking if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include express check-out, a vending machine, and a garden.
Pool
Parking included
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Nov 23 - Nov 24
Total with taxes and fees
Guests of FairBridge Inn Express enjoy access to free WiFi in public areas, meeting rooms, and a business center. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has laundry facilities.
Parking included
Free WiFi
Cozy Corner Motel

Cozy Corner Motel

2 out of 5
284 Sand Springs Rd. Rte 7 Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Dec 2 - Dec 3
Total with taxes and fees
Guests of Cozy Corner Motel enjoy a lazy river, free WiFi in public areas, and a business center. If you drive, take advantage of free parking. Front-desk staff can assist with securing valuables and luggage storage. Other amenities at this family-friendly motel include coffee/tea in a common area, free newspapers, and laundry facilities.
Breakfast included
Parking included
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Nov 27 - Nov 28
Total with taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a TV in a common area.
Pool
Parking included
Willows Motel Williamstown

Willows Motel Williamstown

2 out of 5
480 Main St Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $95 total per night
$95 total
Dec 1 - Dec 2
Total with taxes and fees
Willows Motel Williamstown features an outdoor pool, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include a library, a terrace, and laundry facilities.
Pool
Breakfast included
Maple Terrace Motel

Maple Terrace Motel

2.5 out of 5
555 Main St. Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Nov 23 - Nov 24
Total with taxes and fees
Maple Terrace Motel features free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with concierge services, and offer advice about sights and eateries nearby. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a microwave in a common area, express check-out, and free newspapers.
Pool
Breakfast included
Howard Johnson by Wyndham Williamstown

Howard Johnson by Wyndham Williamstown

2 out of 5
213 Main St Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $101 total per night
$101 total
Nov 23 - Nov 24
Total with taxes and fees
Howard Johnson by Wyndham Williamstown features free WiFi in public areas, conference space, and a business center. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with securing valuables and concierge services. Additional amenities include coffee/tea in a common area, free newspapers, and barbecue grills.
Breakfast included
Parking included
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2 out of 5
980 Pleasant Street Lee MA
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $66 total per night
$66 total
Dec 7 - Dec 8
Total with taxes and fees
Econo Lodge Lee - Great Barrington features free WiFi in public areas and a vending machine. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area.
Breakfast included
Pet friendly
The Villager Motel

The Villager Motel

2 out of 5
953 Simonds Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $77 total per night
$77 total
Dec 1 - Dec 2
Total with taxes and fees
Guests staying at The Villager Motel enjoy free WiFi in public areas, express check-out, and a garden. There's free parking if you drive. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours.
Breakfast included
Parking included
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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.

Cheshire 2 Star Accommodation

    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd Lenox MA
    $91 nightly
    The price is $102 total per night from Dec 14 to Dec 15
    $102 total
    Dec 14 - Dec 15
    Total with taxes and fees
    9/10 Wonderful! (1,004 reviews)
    Quality Inn

    Quality Inn

    170 Housatonic Street Lee MA
    $93 nightly
    The price is $104 total per night from Dec 7 to Dec 8
    $104 total
    Dec 7 - Dec 8
    Total with taxes and fees
    8.2/10 Very Good! (1,000 reviews)
    Howard Johnson by Wyndham Lenox

    Howard Johnson by Wyndham Lenox

    462 Pittsfield Rd Lenox MA
    $79 nightly
    The price is $88 total per night from Nov 23 to Nov 24
    $88 total
    Nov 23 - Nov 24
    Total with taxes and fees
    7.4/10 Good! (823 reviews)

Pet Friendly Motels in Cheshire

    Harbour House Inn

    Harbour House Inn

    725 North State Road Cheshire MA
    $249 nightly
    The price is $264 total per night from Dec 1 to Dec 2
    $264 total
    Dec 1 - Dec 2
    Total with taxes and fees
    9.6/10 Exceptional! (39 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $94 nightly
    The price is $105 total per night from Nov 23 to Nov 24
    $105 total
    Nov 23 - Nov 24
    Total with taxes and fees
    8.6/10 Excellent! (2,136 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $107 nightly
    The price is $120 total per night from Dec 20 to Dec 21
    $120 total
    Dec 20 - Dec 21
    Total with taxes and fees
    8.6/10 Excellent! (1,004 reviews)

Motels

Book a motel in Cheshire
Simple and cost-effective, motels are a great choice for the budget traveler. If all you need is four walls, a roof and a comfy bed for the night, motels are for you. You’ll be spending all your time enjoying the sights and sounds of Cheshire, anyway.

Cheap motels can help you preserve your limited travel funds so you can spend more on good eats, great concerts or fascinating adventures around Cheshire. There’s no reason to spend more on a boutique hotel if you’ll be spending the majority of your time out on the town! Orbitz has a great selection of motels in Cheshire, so start browsing and planning your getaway.

Budget motels make travel a breeze
Cheap motels can make it possible for you to visit Cheshire and see everything it has to offer. They’re good for business travelers, too—budget motels help protect your bottom line. If you live in Cheshire and need somewhere local or “near me” to stay during a home renovation or between moves, a motel is a great option as a short-term solution. You can find motel accommodations near major Cheshire landmarks and off the beaten path.

Not every motel is the same, though. Some provide just the basics, while others offer swimming pools, gyms, cable TV, free Wi-Fi and other services. Extended stay motel rooms usually include a kitchenette and small fridge, which allows you to save even more money by cooking and storing your own food instead of eating out every night.

Is your furry friend coming with you on your trip to Cheshire? Search through Orbitz’s listings of pet-friendly motels in Cheshire to make sure your best friend has a place to stay as well.

Cheshire Motels essential information

Accommodation
24 Motels
Lowest Price
$66
Highest Price
$264
Popular accommodation
Howard Johnson by Wyndham Lenox, FairBridge Inn Express, Cozy Corner Motel, Berkshire Inn, Willows Motel Williamstown, Maple Terrace Motel, Howard Johnson by Wyndham Williamstown, Econo Lodge Lee - Great Barrington, The Villager Motel