Winchester Vacation Rentals, Houses & More


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Areas near Winchester

1 / 4

Nice room in a quiet New England town

  • 1
  • 2
  • 1 night min

$50

Details

Great rentals within 20 miles that match your search

1 / 15

Back Bay Boston Furnished Apartment Rental - 304 Newbury Street Unit 4

  • 1
  • 4
  • Min stay varies

$117

Details

1 / 23

Spacious Studio minutes from Boston

  • Studio
  • 2
  • 1 night min

$99

Details

1 / 13

Large 3BR + Loft-close to Harvard

  • 3
  • 7
  • 2 nights min

$373

Details

1 / 12

Harvard Area 2BD Nicely Furnished Apartment

  • 2
  • 5
  • 2 nights min

$258

Details

1 / 11

Affordable Private Room With Airbed!

  • 1
  • 1
  • 7 nights min

$31

Details

1 / 24

Charming House in Downtown Boston

  • 4
  • 12
  • 3 nights min

$596

Details

1 / 9

New Heart of Newbury Back Bay Boston Studio Apt

  • Studio
  • 2
  • Min stay varies

$109

Details

1 / 1

VR Test

  • 1
  • 1
  • 2 nights min

Inquire for Rates

Details

1 / 21

Heart of Boston - Beacon Hill

  • 1
  • 4
  • Min stay varies

$198

Details

1 / 30

UltraLuxe Apt in Boston Brownstone in Prime Area

  • 4
  • 8
  • 3 nights min

$645

Details

1 / 15

Beacon Hill -- "The Federal Rose" antique house

  • 2
  • 4
  • 5 nights min

$397

Details

1 / 22

TheLedders1 -Fullbed/2 Bth near city/T/Freeparking

  • 1
  • 2
  • 2 nights min

$55

Details

1 / 24

Charlestown Boston Furnished Apartment Rental 12 Mount Vernon Street Unit 2

  • 2
  • 4
  • 4 nights min

$103

Details

1 / 4

TEST PROPERTY - FLIPKEY

  • 4
  • 1
  • 1 night min

$9924

Details

1 / 21

2 BR Luxury Condo, Downtown Boston

  • 2
  • 5
  • 1 night min

$596

Details

1 / 56

Colbyco CitySide - South Boston

  • 5
  • 8
  • 3 nights min

$645

Details

1 / 4

Boston Apartment Fenway/Kenmore TEST

  • 1
  • 2
  • 1 night min

$149

Details

1 / 16

Steps to Nantasket BEACH-BUDGET $-Modern Rental

  • 2
  • 4
  • 7 nights min

$142

Details

1 / 26

Luxurious Comfort Home Close to T and Boston

  • 2
  • 8
  • 1 night min

$276

Details

1 / 23

Sunny Luxury 5 Bed 4 Bath Condo Near Davis Square with 1 Parking

  • 5
  • 8
  • Min stay varies

$452

Details

1 / 15

AWESOME house 3BR with parking

  • 3
  • 8
  • 1 night min

$482

Details

1 / 17

South End Boston Furnished Apartment Rental - 16 East Springfield Street Unit 6

  • 2
  • 6
  • Min stay varies

$177

Details

1 / 16

Close 2T Private Room with AirBed

  • 1
  • 1
  • 7 nights min

$35

Details

1 / 9

Beautiful 2bdrm, Walk to Downtown, Waterfront, Convention Center

  • 2
  • 6
  • 2 nights min

$249

Details

1 / 5

Harvard, MIT, Tufts, MGH -- Visiting Scholars are Welcome!

  • 3
  • 2
  • 2 nights min

$62

Details

1 / 5

Beautiful Spacious Room (SU2-2)

  • 1
  • 1
  • 1 night min

$60

Details

1 / 18

Sunny & Cozy 2 bdrm Duplex, Jamaica Plain, Boston

  • 2
  • 6
  • Min stay varies

$159

Details

1 / 181

Kendall MIT Technology Square I

  • 1
  • 2
  • 1 night min

$198

Details

1 / 6

Sunny one bedroom in Cambridge

  • 1
  • 3
  • 3 nights min

$100

Details

1 / 25

Sunny and quite house in woods near Boston

  • 4
  • 7
  • 1 night min

$154

Details

1 / 24

4 Boston Dwtn Shiny 4BR/2BT walk2all 4 biz&Tour

  • 4
  • 11
  • Min stay varies

$406

Details

1 / 5

One bedroom furnished apartment in North Cambridge

  • 1
  • 3
  • 7 nights min

$213

Details

1 / 24

Your Home Away From Home

  • 1
  • 4
  • 3 nights min

$164

Details

1 / 30

Elegant new renovation of a historic brownstone on a prime South End street

  • 1
  • 3
  • Min stay varies

$184

Details

1 / 18

South End Boston Furnished Apartment Rental - 237 Northampton Street Unit 2

  • 2
  • 6
  • Min stay varies

$158

Details

1 / 19

'Ocean's 26' Nantasket Beach Summer Dream

  • 4
  • 10
  • Min stay varies

$298

Details

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