Winchester Vacation Rentals, Houses & More


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1 / 4

Nice room in a quiet New England town

  • 1
  • 2
  • 1 night min

$50

Details

Great rentals within 30 miles that match your search

1 / 23

Spacious Studio minutes from Boston

  • Studio
  • 2
  • 1 night min

$99

Details

1 / 20

Charming 4 room apartment, minutes from Cambridge and Boston

  • 1
  • 4
  • 3 nights min

$165

Details

1 / 15

Medford

  • 3
  • 8
  • 3 nights min

$300

Details

1
1 / 10

Tufts-Area Large 2BD Apartment

  • 2
  • 5
  • 2 nights min

$200

Details

1 / 11

Beautiful

  • 3
  • 6
  • 3 nights min

$400

Details

1 / 7

Spacious 3 bedroom near everything

  • 3
  • 5
  • 3 nights min

$195

Details

1 / 7

Amsden Place

  • 2
  • 4
  • Min stay varies

$150

Details

1 / 10

Room with private entrance

  • 1
  • 2
  • 2 nights min

$80

Details

1 / 24

Open Luxury 4 Bed 3 Bath Condo with 1 Parking

  • 4
  • 8
  • Min stay varies

$400

Details

1
1 / 23

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

  • 5
  • 8
  • Min stay varies

$455

Details

1 / 20

Beautiful home close to Boston

  • 3
  • 10
  • 2 nights min

$275

Details

1 / 15

BEAUTIFUL Apt 2BR/1B close to train station

  • 2
  • 6
  • 1 night min

$282

Details

1 / 1

4 BR Medford Square

  • 4
  • 4
  • 1 night min

$500

Details

1
1 / 24

HUGE POOL HOUSE 4 BedRooms 2.5 Bathrooms ,3 Parking spots & a POOL!

  • 5
  • 16
  • Min stay varies

$499

Details

1 / 21

Colbyco North Cambridge

  • 2
  • 6
  • 3 nights min

$350

Details

1 / 13

Historic 3 bd loft short walk to Davis Sq redline

  • 3
  • 6
  • 1 night min

$400

Details

1
1 / 14

Lovely Apt. - Davis & Porter Sq. - Harvard, Tufts, MIT, Mass. General Hospital

  • 2
  • 4
  • 2 nights min

$200

Details

1 / 5

One bedroom furnished apartment in North Cambridge

  • 1
  • 3
  • 7 nights min

$215

Details

1 / 4

Private Queen in Cambridge

  • 1
  • 3
  • 1 night min

$70

Details

1 / 5

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

  • 3
  • 2
  • 2 nights min

$62

Details

1 / 5

Studio apartments near Harvard Square Cambridge

  • Studio
  • 2
  • 7 nights min

$143

Details

1 / 4

Room in Huge Modern, 4BR Condo (2)

  • 1
  • 1
  • 30 nights min

$60

Details

1 / 11

Harvard Area 2BD Garden Level Apt

  • 2
  • 5
  • 2 nights min

$220

Details

1
1 / 12

Harvard Area 2BD Nicely Furnished Apartment

  • 2
  • 5
  • 2 nights min

$260

Details

1 / 15

3 Bedroom with parking in West Cambridge

  • 3
  • 9
  • 2 nights min

$285

Details

1 / 5

Beautiful Spacious Room (SU2-2)

  • 1
  • 1
  • 1 night min

$60

Details

1 / 4

Beautiful Spacious Room (SU1-1)

  • 1
  • 1
  • 1 night min

$60

Details

1 / 7

Harvard Sq King bed

  • 1
  • 3
  • 1 night min

$120

Details

1 / 12

SUNNY HOME 9 MINUTE WALK TO HARVARD SQUARE

  • 3
  • 7
  • 7 nights min

$643

Details

1
1 / 12

COZY&HOMEY Apartment 2BR/1Bath + 2 free parking!!

  • 2
  • 8
  • 1 night min

$249

Details

1 / 16

AWESOME & BIG House 4BR/1fullBath+ 2 free Parking

  • 4
  • 10
  • Min stay varies

$399

Details

1 / 34

Cambridge/Harvard/MIT/Mass General/Boston/Tufts/BB&N

  • 4
  • 12
  • Min stay varies

$350

Details

1
1 / 46

Harvard/MIT/Mass General/Boston Univ/ Cambridge

  • 4
  • 12
  • Min stay varies

$550

Details

1 / 10

Studio+ Galley Kitchen: Near Harvard & Porter Sq

  • 1
  • 4
  • 1 night min

$122

Details

1 / 25

Harvard Square Steps to Law School- 2 Bedroom apt

  • 2
  • 4
  • Min stay varies

$235

Details

3
1 / 20

Clarendon Road

  • 1
  • 2
  • Min stay varies

$150

Details

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