Book Boutique Hotels in Winchester, MA

AWARD WINNER
Cambria Hotel Boston Somerville
515 Somerville Avenue,
Somerville, MA, 02143, US
8.1 km from Winchester, MA, US
4.69 stars rating. Exceptional. 1252 reviews
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Strikethrough Rate:~~$219~~Discounted rate:$204USD/night
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Quality Inn Boston-Revere
100 Morris Street,
Revere, MA, 02151, US
9.27 km from Winchester, MA, US
3.47 stars rating. Good. 731 reviews
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Strikethrough Rate:~~$122~~Discounted rate:$113USD/night
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Comfort Inn & Suites Logan International Airport
85 American Legion Hwy.,
Revere, MA, 02151, US
12.03 km from Winchester, MA, US
4.45 stars rating. Excellent. 4498 reviews
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Strikethrough Rate:~~$165~~Discounted rate:$149USD/night
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Comfort Inn Danvers - Boston North Shore
102 Newbury Street,
Danvers, MA, 01923, US
18.39 km from Winchester, MA, US
4.13 stars rating. Very Good. 420 reviews
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Strikethrough Rate:~~$132~~Discounted rate:$119USD/night
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Rodeway Inn Logan International Airport
309 American Legion Highway, Route 60 West,
Revere, MA, 02151, US
11.7 km from Winchester, MA, US
2.99 stars rating. Fair. 1223 reviews
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Strikethrough Rate:~~$114~~Discounted rate:$107USD/night
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Cambria Hotel Boston Downtown - Seaport
6 West Broadway,
Boston, MA, 02127, US
13.84 km from Winchester, MA, US
3.78 stars rating. Good. 1128 reviews
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Strikethrough Rate:~~$251~~Discounted rate:$239USD/night
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Comfort Inn Randolph - Boston
1374 North Main Street,
Randolph, MA, 02368, US
28.52 km from Winchester, MA, US
3.68 stars rating. Good. 1372 reviews
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Strikethrough Rate:~~$126~~Discounted rate:$113USD/night
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AWARD WINNER
Clarion Inn Nashua
10 St. Laurent St.,
Nashua, NH, 03064, US
46.29 km from Winchester, MA, US
4.27 stars rating. Excellent. 587 reviews
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Strikethrough Rate:~~$129~~Discounted rate:$116USD/night
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Comfort Inn Boston Milford
24 Beaver Street,
Milford, MA, 01757, US
44.29 km from Winchester, MA, US
3.83 stars rating. Good. 315 reviews
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Strikethrough Rate:~~$115~~Discounted rate:$104USD/night
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Country Inn & Suites by Radisson, Brockton (Boston), MA
50 Christy's Drive,
Brockton, MA, 02301, US
40.92 km from Winchester, MA, US
4.29 stars rating. Excellent. 242 reviews
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Strikethrough Rate:~~$129~~Discounted rate:$120USD/night
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Comfort Inn Rockland - Boston
850 Hingham St.,
Rockland, MA, 02370, US
37.76 km from Winchester, MA, US
3.7 stars rating. Good. 974 reviews
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Strikethrough Rate:~~$114~~Discounted rate:$103USD/night
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AWARD WINNER
Essex Street Inn & Suites, an Ascend Collection Hotel
7 Essex Street,
Newburyport, MA, 01950, US
45.42 km from Winchester, MA, US
4.59 stars rating. Excellent. 817 reviews
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Strikethrough Rate:~~$165~~Discounted rate:$150USD/night
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Econo Lodge Sharon - Foxborough
775 Providence Highway,
Sharon, MA, 02067, US
37.24 km from Winchester, MA, US
3.01 stars rating. Fair. 530 reviews
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Strikethrough Rate:~~$100~~Discounted rate:$93USD/night
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NEW TO CHOICE
Comfort Inn - Dedham-Boston MetroWest
235 Elm St.,
Dedham, MA, 02026-4542, US
25.16 km from Winchester, MA, US
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Coming soonStart booking Aug 05, 2026
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NEW HOTEL
Cambria Hotel Boston Logan Airport
155 Porter Street,
East Boston, MA, 02128, US
12.33 km from Winchester, MA, US
No Reviews Yet
Coming soonStart booking Jun 16, 2026
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Winchester hotels by brand

Country Inn Suites Hotels

Econo Lodge Hotels

Quality Inn Hotels

Rodeway Inn Hotels

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Boutique hotels

13 of 15 hotels in Winchester

Highest Price

$239

Lowest Price

$93

Avg. rating

13 Boutique hotels near Winchester, MA, US

Cambria Hotel Boston Somerville

Quality Inn Boston-Revere

Comfort Inn & Suites Logan International Airport

Comfort Inn Danvers - Boston North Shore

Rodeway Inn Logan International Airport

Cambria Hotel Boston Downtown - Seaport

Comfort Inn Randolph - Boston

Clarion Inn Nashua

Comfort Inn Boston Milford

Country Inn & Suites by Radisson, Brockton (Boston), MA

Comfort Inn Rockland - Boston

Essex Street Inn & Suites, an Ascend Collection Hotel

Econo Lodge Sharon - Foxborough

Change your dates to book properties below.

Comfort Inn - Dedham-Boston MetroWest

Cambria Hotel Boston Logan Airport

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Winchester hotels by brand

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13 of 15 hotels in Winchester

$239

$93

3.4 (14089 reviews)