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Airbnb, Vacation rentals and hotel deals in Winchester, MA

9.2 (488 reviews)
Hampton Inn Boston Woburn
Hotel · 2 Guests · 1 Bedroom
$141 /night
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9.0 (2 reviews)
Standard King Room at Studio Allston Hotel
Holiday home · 2 Guests · 1 Bedroom
$117 /night*
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Studio Allston Hotel Boston
Hotel · 2 Guests · 1 Bedroom
$121 /night
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8.6 (216 reviews)
Holiday Inn Express & Suites Boston - Cambridge, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$141 /night
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8.2 (380 reviews)
Aloft Lexington
Hotel · 2 Guests · 1 Bedroom
$113 /night
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8.2 (735 reviews)
Hilton Boston-Woburn
Hotel · 2 Guests · 1 Bedroom
$138 /night
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7.7 (445 reviews)
Best Western Plus New Englander
Hotel · 2 Guests · 1 Bedroom
$125 /night
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8.4 (213 reviews)
Homewood Suites by Hilton - Boston/Billerica-Bedford
Hotel · 2 Guests · 1 Bedroom
$142 /night
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9.0 (64 reviews)
Near scenic Fresh Pond, Charles river, shops, Harvard Sq access , Free parking
Apartment · 2 Guests · 1 Bedroom
$135 /night*
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#302 Waltham House by Zen Living
Holiday home · 2 Guests · 1 Bedroom
$110 /night*
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4.0 (1 review)
Vacation Day Is Always a Great Idea! Near Downtown, Liberty Ride Trolley Tour
Holiday home · 2 Guests · 1 Bedroom
$90 /night*
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9.8 (8 reviews)
The King's Room (Room 4) at The Perthshire House
Hostel · 2 Guests · 1 Bedroom
$102 /night*
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8.0 (164 reviews)
Sonesta Simply Suites Boston Burlington
Hotel · 2 Guests · 1 Bedroom
$112 /night
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7.0 (754 reviews)
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Hotel · 2 Guests · 1 Bedroom
$85 /night
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8.1 (431 reviews)
Holiday Inn Express Saugus Logan Airport, an IHG hotel
Hotel · 2 Guests · 1 Bedroom
$102 /night
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6.3 (209 reviews)
Extended Stay America Suites - Boston - Burlington
Hotel · 2 Guests · 1 Bedroom
$106 /night
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9.2 (579 reviews)
Hotel 1868
Hotel · 2 Guests · 1 Bedroom
$106 /night
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7.6 (4 reviews)
#202 Waltham House by Zen Living
Holiday home · 2 Guests · 1 Bedroom
$87 /night*
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6.9 (156 reviews)
Extended Stay America Suites - Boston - Woburn
Hotel · 2 Guests · 1 Bedroom
$121 /night
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8.8 (175 reviews)
Hampton Inn & Suites Watertown Boston, Ma
Hotel · 2 Guests · 1 Bedroom
$126 /night
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Airbnb, Vacation House with Air Conditioning in Winchester, MA

Melrose 5-bedroom house
Holiday home · 2 Guests · 1 Bedroom
$478 /night
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10 (1 review)
Davis Square Inn
B & B · 2 Guests · 1 Bedroom
$173 /night
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The Morrison House Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$173 /night
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What Are The Most Popular Amenities in Winchester, MA?
Trending Vacation Rental Amenities in Winchester, MA
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The above reveals the top rental amenities and the property numbers associated with each of them in Winchester. In Winchester, 1071 rentals offer Internet or Wifi, 984 rentals offer Air Conditioning, 943 rentals offer TV. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Pool, Hot Tub.
Which Price Range Is Most Typical in Winchester, MA Area?
Vacation Apartment & House Rental Price Information in Winchester, MA
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The graph shows the percentages of vacation homes in each price bucket. Winchester has the largest percentage (18.13%) of homes in $150 - $200 price range.
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What Are The Most Liked Rental Accommodations in Winchester, MA?
Most Picked Accommodations in Winchester, MA
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Before visiting Winchester, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: Apartment, House, Condo, Bed And Breakfast, Studio, Townhome, Cottage, Guest House, Estate, Yacht, Villa, Boat, Hostel, Hotel, House Boat, Chateau / Country House, Farmhouse, Bungalow, Corporate Apartment. Apartment is the most-liked rental type, with the largest percentage of 45.89%. The biggest home in this area available for rent is around 8050 square feet.The least popular accommodation in Winchester is Bungalow rentals
How Many Rental Accommodations Are Pets Friendly in Winchester, MA?
Percentage of Pet Friendly Rental Properties in Winchester, MA
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24.22% of vacation homes in Winchester are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Must-Visit Trails in Winchester, MA?
Top Trails In Winchester, MA
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Here are the trails we recommend in Winchester: Horn Pond Trail, Whipple Hill Reserve, Skyline Trail Loop, Two Towers Hike, Southern Middlesex Fells Loop, Middlesex Fells Reservation Loop Trail, Arlington Reservoir Trail, East Middlesex Fells Reservation Loop Trail, West Middlesex Fells Reservoir Trail, West Middlesex Fells Reservation Bike Loop.
Where Are The Campgrounds in Winchester, MA Area?
Campgrounds Recommendations In Winchester, MA
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The best RV campgrounds here in Winchester are: Winter Island Park Campground, Harold Parker Campground, Salisbury Beach State Reservation Campground, Wompatuck Campground, Tidewater Campground, Wakeda Campground, Green Gate Campground, Circle CG Farm Campground, Cross Winds Family Campground, Pearl Hill Campground.
What are the Airports in Winchester, MA?
Airports Options in Winchester, MA
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Other Vacation Rentals Ideas

Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Winchester, MA

House in Arlington, near Boston, Harvard, MIT, and Tuft University
Holiday home · 2 Guests · 1 Bedroom
$280 /night*
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9.0 (2 reviews)
#301 Waltham House by Zen Living
Holiday home · 2 Guests · 1 Bedroom
$98 /night*
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10 (1 review)
Explore North Shore from Boston! Kitchen, Pets Allowed, Near Burlington Mall!
Holiday home · 2 Guests · 1 Bedroom
$126 /night*
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Airbnb, Pet Friendly Vacation Condo in Winchester, MA

Pleasant 2br apartment in Cambridge
Apartment · 2 Guests · 1 Bedroom
$166 /night
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Upscale 3 bedroom 2 bathroom Cambridge
Apartment · 2 Guests · 1 Bedroom
$300 /night
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Airbnb, Vacation Condo with Fireplace in Winchester, MA

9.0 (8 reviews)
★Contemporary Studio10min to Boston w/ free Parking★
Apartment · 2 Guests · 1 Bedroom
$124 /night*
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Upscale 3 bedroom 2 bathroom Cambridge
Apartment · 2 Guests · 1 Bedroom
$300 /night
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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