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Cheshire Hotels and B&Bs

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Hotels & B&Bs / Inns travellers recommend

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Your selections 25 km
Cheshire B&Bs / Inns (1)
Ranked #1 of 1 Cheshire B&B and Inns
5 of 5 stars 42 reviews
Traveller photos (19) | Map
Recommended nearby hotels and B&Bs
Garden Gables Inn, Lenox
INR13,253 - 19,796 per night*
24.4 km from Cheshire
Special offer Up to 50% off 2nd night*
+1 888-243-0193
E-mail hotel
Special offer Up to 50% off 2nd night*
Garden Gables Inn Slideshow
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Ranked #1 of 24 Lenox B&B and Inns
5 of 5 stars 277 reviews
Professional photos | Traveller photos (69) | Map
3.0 of 5 Hampton Terrace Bed and Breakfast Inn, Lenox
INR10,904 - 12,414 per night*
25.0 km from Cheshire
Offers & Announcements Romantic Weekend Special
+1 +1 800-203-0656
E-mail hotel
Offers & Announcements Romantic Weekend Special
Hampton Terrace Bed and Breakfast Inn Slideshow
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Ranked #2 of 24 Lenox B&B and Inns
5 of 5 stars 445 reviews
Professional photos | Traveller photos (31) | Map
3.0 of 5 Gateways Inn, Lenox
INR9,395 - 18,733 per night*
25.0 km from Cheshire
Offers & Announcements Free room upgrade
+1 413-637-2532
E-mail hotel
Offers & Announcements Free room upgrade
Gateways Inn Slideshow
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Ranked #3 of 24 Lenox B&B and Inns
5 of 5 stars 38 reviews
Professional photos | Traveller photos (11) | Map
Berkshires Shirakaba Guest House, New Ashford
INR19,292 - 21,529 per night*
7.7 km from Cheshire
E-mail hotel
+1 413-458-1800
Berkshires Shirakaba Guest House Slideshow
Ranked #1 of 1 New Ashford B&B and Inns
5 of 5 stars 54 reviews
Traveller photos (27) | Map
Birchwood Inn, Lenox
INR12,191 - 12,191 per night*
24.2 km from Cheshire
+1 800-524-1646
E-mail hotel
Birchwood Inn Slideshow
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Ranked #5 of 24 Lenox B&B and Inns
5 of 5 stars 181 reviews
Professional photos | Traveller photos (30) | Map
3.0 of 5 1896 House - Barnside Inn, Williamstown
INR11,016 - 11,016 per night*
15.6 km from Cheshire
1896 House - Barnside Inn Slideshow
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Ranked #1 of 12 Williamstown B&B and Inns
5 of 5 stars 63 reviews
Professional photos | Traveller photos (29) | Map
2.5 of 5 Hampton Inn & Suites Berkshires, Lenox
INR7,885 - 22,424 per night*
19.7 km from Cheshire
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Ranked #2 of 15 hotels in Lenox
4.5 of 5 stars 124 reviews
Professional photos | Traveller photos (65) | Map
Churchill House Bed & Breakfast, New Lebanon, NY
INR5,312 - 13,980 per night*
22.8 km from Cheshire
Offers & Announcements Stay 4 Get 1 Free
+1 518-766-5852
E-mail hotel
Offers & Announcements Stay 4 Get 1 Free
Churchill House Bed & Breakfast Slideshow
Ranked #1 of 3 New Lebanon B&B and Inns
4.5 of 5 stars 18 reviews
Traveller photos (14) | Map
MAPLE TERRACE MOTEL, Williamstown
INR4,865 - 7,829 per night*
16.5 km from Cheshire
+1 413-458-9677
E-mail hotel
MAPLE TERRACE MOTEL Slideshow
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Ranked #1 of 12 hotels in Williamstown
4.5 of 5 stars 107 reviews
Professional photos | Traveller photos (25) | Map
Blackinton Manor Bed & Breakfast, North Adams
INR7,549 - 12,302 per night*
15.8 km from Cheshire
Special offer 2 Free MASS MoCA Ticket
E-mail hotel
413-663-5795
Special offer 2 Free MASS MoCA Ticket
Blackinton Manor Bed & Breakfast Slideshow
Ranked #1 of 1 North Adams B&B and Inns
4.5 of 5 stars 79 reviews
Traveller photos (27) | Map
Berkshire Hills Motel, Williamstown
INR3,299 - 8,332 per night*
14.9 km from Cheshire
Special offer $79 per night
800-388-9677
E-mail hotel
Special offer $79 per night
Berkshire Hills Motel Slideshow
Ranked #2 of 12 hotels in Williamstown
4.5 of 5 stars 79 reviews
Traveller photos (25) | Map
BEST WESTERN Berkshire Hills Inn & Suites, Pittsfield
INR5,256 - 12,246 per night*
18.7 km from Cheshire
Special offer Earn a $50 Gift Card
800-568-8520
Special offer Earn a $50 Gift Card
BEST WESTERN Berkshire Hills Inn & Suites Slideshow
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Ranked #1 of 9 hotels in Pittsfield
4.5 of 5 stars 16 reviews
Professional photos | Traveller photos (9) | Map
3.0 of 5 Cornell in Lenox, Lenox
INR7,437 - 22,200 per night*
23.9 km from Cheshire
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Ranked #10 of 24 Lenox B&B and Inns
4.5 of 5 stars 125 reviews
Professional photos | Traveller photos (12) | Map
Topia Inn, Adams
INR11,743 - 16,496 per night*
7.6 km from Cheshire
Special offer Get the 2nd night 25...
E-mail hotel
+1 413-743-9600
Special offer Get the 2nd night 25% off
Topia Inn Slideshow
Ranked #1 of 2 Adams B&B and Inns
4.5 of 5 stars 25 reviews
Traveller photos (10) | Map
1896 House - Brookside & Pondside Motels, Williamstown
INR3,858 - 9,450 per night*
15.6 km from Cheshire
+1 +1888-999-1896
1896 House - Brookside & Pondside Motels Slideshow
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Ranked #3 of 12 hotels in Williamstown
4.5 of 5 stars 114 reviews
Professional photos | Traveller photos (22) | Map
3.5 of 5 The Porches Inn at MASS MoCA, North Adams
INR7,270 - 17,894 per night*
16.2 km from Cheshire
Special offer Room, Dinner + Mass...
E-mail hotel
+1 413.664.0400
Special offer Room, Dinner + Mass MOCA!
The Porches Inn at MASS MoCA Slideshow
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Ranked #1 of 3 hotels in North Adams
4.5 of 5 stars 165 reviews
Professional photos | Traveller photos (85) | Map
3.0 of 5 White Horse Inn, Pittsfield
INR7,773 - 10,569 per night*
15.9 km from Cheshire
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Ranked #1 of 5 Pittsfield B&B and Inns
4.5 of 5 stars 22 reviews
Professional photos | Map
Bucksteep Manor Inn and Conference Center, Becket
INR6,710 - 11,184 per night*
22.9 km from Cheshire
Ranked #1 of 2 Becket B&B and Inns
4.5 of 5 stars 23 reviews
Traveller photos (2) | Map
Yankee Inn, Lenox
INR4,418 - 16,161 per night*
19.6 km from Cheshire
800-835-2364
Yankee Inn Slideshow
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Ranked #6 of 15 hotels in Lenox
4 of 5 stars 150 reviews
Professional photos | Traveller photos (58) | Map
The Guest House at Field Farm, Williamstown
INR4,753 - 10,066 per night*
14.1 km from Cheshire
Ranked #2 of 12 Williamstown B&B and Inns
4.5 of 5 stars 16 reviews
Traveller photos (4) | Map
Mount Greylock Inn, Adams
INR4,697 - 8,612 per night*
7.3 km from Cheshire
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Ranked #2 of 2 Adams B&B and Inns
4.5 of 5 stars 18 reviews
Professional photos | Traveller photos (3) | Map
The Village Inn Bed and Breakfast, Lenox
INR6,822 - 14,595 per night*
24.9 km from Cheshire
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Ranked #11 of 24 Lenox B&B and Inns
4.5 of 5 stars 86 reviews
Professional photos | Traveller photos (21) | Map
3.5 of 5 The Orchards Hotel, Williamstown
INR9,283 - 18,677 per night*
16.1 km from Cheshire
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Ranked #4 of 12 hotels in Williamstown
4 of 5 stars 131 reviews
Professional photos | Traveller photos (24) | Map
Williamstown Motel, Williamstown
INR2,964 - 9,954 per night*
15.8 km from Cheshire
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Ranked #5 of 12 hotels in Williamstown
4 of 5 stars 53 reviews
Professional photos | Traveller photos (2) | Map
Hitchcock House Bed and Breakfast, New Lebanon, NY
INR4,753 - 6,990 per night*
23.2 km from Cheshire
No photo provided
Ranked #2 of 3 New Lebanon B&B and Inns
4.5 of 5 stars 4 reviews
Map
River Bend Farm, Williamstown
INR4,753 per night*
19.0 km from Cheshire
Ranked #3 of 12 Williamstown B&B and Inns
4.5 of 5 stars 14 reviews
Traveller photos (3) | Map
Steep Acres Farm, Williamstown
20.1 km from Cheshire
No photo provided
Ranked #4 of 12 Williamstown B&B and Inns
4.5 of 5 stars 7 reviews
Traveller photos (4) | Map
3.0 of 5 The Inn at Richmond, Richmond
INR9,842 - 19,125 per night*
23.5 km from Cheshire
E-mail hotel
+1413.698.2566
The Inn at Richmond Slideshow
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Ranked #1 of 3 Richmond B&B and Inns
4.5 of 5 stars 11 reviews
Professional photos | Traveller photos (9) | Map
3.0 of 5 Wyndham at Bentley Brook, Hancock
INR8,556 - 24,213 per night*
10.5 km from Cheshire
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Ranked #1 of 4 hotels in Hancock
4 of 5 stars 91 reviews
Professional photos | Traveller photos (101) | Map