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Winchester Massachusetts Hotels & Motels

Find hotels in Winchester using the list and search tools below. Search for cheap and discounted hotel and motel rates in or near Winchester, MA for your corporate or personal leisure travel. We show the best Winchester, Massachusetts hotel and motel rooms. Browse the Winchester area hotels to find the perfect lodging! Please use the provided map of the Winchester hotels. Booking 5+ Rooms? Find Winchester Group Hotel Discounts

The Winchester center point is about 2 miles northeast of Arlington Center and 3 miles north of East Arlington.

Winchester Hotels, Motels & Accommodations

Hampton by Hilton Boston Woburn Hotel
+1-888-690-5247
371 Washington St., Woburn, MA 01801 ~0.63 miles northeast of Winchester
  • 4 star Suburban hotel
  • 5 floors in hotel
Comfort Inn Woburn : 14 Hill St.
+1-888-305-3366
14 Hill St., Woburn, MA 01801 ~1.97 miles northeast of Winchester
  • Low-priced Suburban hotel
  • 65 rooms in property
From$60
Very Good 4.0 /5Review Score CallBookMore Details
Best Western Plus New Englander
+1-800-881-1523
1 Rainin Rd., Woburn, MA 01801-4627 ~2.00 miles northeast of Winchester
  • Three Star Suburban property
  • Check in: 3pm
  • Breakfast is mediocre
  • Most guests liked the big bathroom
Courtyard by Marriott Woburn Boston North in Woburn
+1-888-283-3404
700 Unicorn Park Dr., Woburn, MA 01801 Website ~2.44 miles northeast of Winchester
  • Three Star Suburban hotel
  • Hotel has 6 floors
  • Excellent location
  • Friendly atmosphere
Crowne Plaza Boston Woburn
+1-866-221-8581
15 Middlesex Canal Park, Woburn, MA 01801 ~3.00 miles north of Winchester
  • Expensive Suburban hotel
  • 197 rooms in hotel
  • Gluten free bread
  • Air conditioning was criticized by 79%
From$105
Very Good 4.0 /5Recent Reviews CallBookMore Details
Hyatt Place Boston / Medford - Medford
+1-866-429-5787
116 Riverside Ave., Medford, MA 02155 ~3.11 miles southeast of Winchester
  • Three Star Suburban property
  • 8 floors in hotel
  • Air conditioning was criticized by 95%
  • Awesome beds
From$89
Very Good 4.0 /5Reviews CallBookMore Details
Hampton Inn Boston Woburn in Woburn
+1-888-690-5281
372 Washington St., Woburn, MA 01801 ~3.18 miles north of Winchester
  • Affordable property
  • Hotel has 132 rooms
Fairfield Inn Boston Woburn / Burlington - Woburn
+1-888-690-5247
285 Mishawum Rd., Woburn, MA 01801 ~3.33 miles north of Winchester
  • Three Star Suburban hotel
  • Check in time: 3:00 PM
  • For 51%, maintenance was acceptable
  • Parking was ok, according to 50%
Holiday Inn Express Boston North Woburn
+1-888-305-3366
315 Mishawum Rd., Woburn, MA 01801 ~3.35 miles north of Winchester
  • 3-star Suburban property
  • Fitness center on property
Courtyard by Marriott Andover - Woburn
+1-800-881-1523
240 Mishawum Rd., Woburn, MA 01801 ~3.35 miles north of Winchester
  • Affordable Suburban property
  • Fitness center on property
Extended Stay America Boston Woburn : 831 Main St.
+1-888-283-3404
831 Main St., Woburn, MA 01801 ~3.50 miles north of Winchester
  • Three Star Suburban hotel
  • Free complimentary breakfast
  • Rooms are not good
  • Housekeeping can be a problem
Hyatt House Boston / Burlington in Burlington
+1-866-221-8581
2 Van De Graaff Dr., Burlington, MA 01803 ~3.51 miles northwest of Winchester
  • Mid-scale Suburban property
  • 3 floors in hotel
  • Average wifi quality
  • Comfortable beds
Red Roof Plus Boston Woburn
+1-866-429-5787
19 Commerce Way, Woburn, MA 01801 Website ~3.51 miles north of Winchester
  • Low-priced Suburban hotel
  • 159 rooms in property
  • Dingy hallway
  • Great parking, according to 90%
From$59
Very Good 4.0 /5Read Reviews CallBookMore Details
Homewood Suites by Hilton Boston / Cambridge / Arlington
+1-888-690-5281
1 Massachusetts Ave., Arlington, MA 02474 ~3.70 miles south of Winchester
  • Mid-scale Suburban property
  • Check in time: 3:00PM
Boston Marriott Burlington in Burlington
+1-888-690-5247
1 Burlington Mall Rd., Burlington, MA 01803 ~3.90 miles northwest of Winchester
  • 4 star Suburban hotel
  • 4 suites in hotel
From$119
Very Good 4.0 /5Guest Reviews CallBookMore Details
AC Hotel by Marriott Boston Cambridge - Cambridge
+1-888-305-3366
10 Acorn Park Dr., Cambridge, MA 02140 ~4.00 miles south of Winchester
  • Four-star Suburban hotel
  • Hotel has 150 rooms
From$113
Very Good 4.5 /5Reviews CallBookMore Details
Sonesta Es Suites Burlington Boston - Burlington
+1-800-881-1523
11 Old Concord Rd., Burlington, MA 01803 ~4.01 miles west of Winchester
  • 3 star Suburban property
  • 4 floors in property
From$75
Very Good 4.5 /5Read Reviews CallBookMore Details
Hilton Garden Inn Boston Burlington - Burlington
+1-888-283-3404
5 Wheeler Rd., Burlington, MA 01803 ~4.05 miles west of Winchester
  • Affordable Suburban hotel
  • 6 meeting rooms in property
From$89
Very Good 4.0 /5Review Score CallBookMore Details
Execustay at Cambridge Park - Cambridge
+1-866-221-8581
30 Cambridge Park Dr., Cambridge, MA 02140 ~4.25 miles south of Winchester
  • 3 star property
  • Check-in time: 3:30
Residence Inn Marriott Boston / Woburn
+1-866-429-5787
300 Presidential Way, Woburn, MA 01801 ~4.51 miles north of Winchester
  • Mid-scale Suburban property
  • Fitness / Gym is on-site
From$110
Very Good 4.5 /5Read Reviews CallBookMore Details
Extended Stay America Boston / Burlington - Burlington
+1-888-690-5281
40 South Ave., Burlington, MA 01803 ~4.55 miles west of Winchester
  • Low Cost Suburban hotel
  • 140 rooms in hotel
  • Almost all guests thought they were poorly maintained
  • Air conditioner wouldn't work
Freepoint Hotel Cambridge Tapestry Collection by Hilton
+1-888-690-5247
220 Alewife Brook Pkwy., Cambridge, MA 02138 Website ~4.61 miles south of Winchester
  • Four star Downtown hotel
  • Hotel has an eco-friendly policy See policy
From$75
Very Good 4.0 /5Read Reviews CallBookMore Details
Porter Square Hotel in Cambridge
+1-888-305-3366
1924 Massachusetts Ave., Cambridge, MA 02140 ~4.64 miles south of Winchester
  • Mid-scale property
  • 65 rooms in property
From$90
Very Good 4.5 /5Review Score CallBookMore Details
AC Marriott Boston North
+1-800-881-1523
95 Station Landing, Medford, MA 02155 ~4.66 miles southeast of Winchester
  • Mid-scale Suburban property
  • 5 floors in hotel
From$134
Very Good 4.5 /5Reviews CallBookMore Details
Hotel 1868 in Cambridge
+1-888-283-3404
1868 Massachusetts Ave., Cambridge, MA 02140 ~4.74 miles south of Winchester
  • Midscale hotel
  • Check-in time: 15:00
Next 25 Winchester Hotels >  [1 - 25 of 50]    
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Graph: Upcoming 20 Days of Winchester Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Winchester, MA discounts available. The chart reflects the cheapest Winchester hotel for each day and each star rating category.

FAQs about hotels in Winchester

What are the most favored hotels in Winchester?

The Inn at Hastings Park Relais & Châteaux, Courtyard by Marriott Woburn Boston North and Hyatt House Boston are the best rated hotels based on customer reviews in the last 365 days.

What are the most high-end hotels in Winchester?

Hampton by Hilton Boston Woburn Hotel, Crowne Plaza Boston Woburn and Boston Marriott Burlington are the top 3 luxury hotels near Winchester city center.

What hotels are closest to the city center of Winchester?

Hampton by Hilton Boston Woburn Hotel, Comfort Inn Woburn, and Best Western Plus New Englander are the properties closest to Winchester city center.

How much does a cheap hotel in Winchester cost per night?

In the last year, a 2 star hotel in Winchester can be as cheap as $130.84 per night. (based on HotelPlanner prices)

How much does a 3 star hotel in Winchester cost per night?

In the last year, the average 3 star hotel in Winchester has been $157.16 per night. (based on HotelPlanner prices)

How much does a 4-5 star hotel in Winchester cost?

In the last year, the average 4 star hotel in Winchester has been $216.79 per night. (based on HotelPlanner prices)

What are the best independent hotels in Winchester?

The Inn at Hastings Park Relais & Châteaux, Porter Square Hotel and The Row Hotel Boston are the best rated independent hotels (not part of a big brand).

What are the most popular Marriott hotels in Winchester?

Courtyard by Marriott Woburn Boston North, Residence Inn Marriott Boston and AC Marriott Boston North are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the best Choice Hotels branded hotels in Winchester?

Comfort Inn Woburn, Quality Inn Revere and Quality Inn & Suites Lexington are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best IHG hotels in Winchester?

Crowne Plaza Boston Woburn, Holiday Inn Express Boston North Woburn and Holiday Inn Boston Bunker Hill are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

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