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Holiday Homes in Winchester

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44 rentals in Winchester.
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A private, clean, quiet, room at a house in Winchester.Close to train 93 and 95., holiday rental in Winchester

A private, clean, quiet, room at a house in Winchester.Close to train 93 and 95.

1 bedroom
1 bathroom
Sleeps 1
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Boston Cozy home, Near Tufts, Encore Casino, TD Garden, all major hospitals, holiday rental in Winchester

Boston Cozy home, Near Tufts, Encore Casino, TD Garden, all major hospitals

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A charming modern suburban 3 bedroom condo close to Boston, holiday rental in Winchester

A charming modern suburban 3 bedroom condo close to Boston

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1891 Victorian Home Near Harvard, holiday rental in Winchester

1891 Victorian Home Near Harvard

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Clarendon Road, holiday rental in Winchester

Clarendon Road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Welcoming 7 room house <15 miles to Boston, Salem & casino, holiday rental in Winchester

Welcoming 7 room house <15 miles to Boston, Salem & casino

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Gorgeous, Top Floor Condominium Steps Away From Everything & Minutes To Boston!, holiday rental in Winchester

Gorgeous, Top Floor Condominium Steps Away From Everything & Minutes To Boston!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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30 night min, Private, Historic, Near Fresh Pond,  Charles rvr, shops,  Hvd Sqr, holiday rental in Winchester

30 night min, Private, Historic, Near Fresh Pond, Charles rvr, shops, Hvd Sqr

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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3br/1140sf Cambridge Winter Rental By Harvard Sq., holiday rental in Winchester

3br/1140sf Cambridge Winter Rental By Harvard Sq.

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Apt. - Davis & Porter Sq. - Harvard, Tufts, MIT, Mass. General Hospital, holiday rental in Winchester

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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4 bedroom Colonial in Lexington neighborhood, holiday rental in Winchester

4 bedroom Colonial in Lexington neighborhood

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Clarendon Road, holiday rental in Winchester

Clarendon Road

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful, holiday rental in Winchester

Beautiful

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunny and immaculately clean 3 bed/2 bath - 5 min walk to Alewife T (red line), holiday rental in Winchester

Sunny and immaculately clean 3 bed/2 bath - 5 min walk to Alewife T (red line)

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Colonial Two Bedroom Basement Apartment, holiday rental in Winchester

Charming Colonial Two Bedroom Basement Apartment

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Double Room near Harvard Square (Share bathroom), holiday rental in Winchester

Cozy Double Room near Harvard Square (Share bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 BR Medford Square, holiday rental in Winchester

4 BR Medford Square

4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Room with private entrance, holiday rental in Winchester

Room with private entrance

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sweet studio 15 minutes from Bos.Logan Airport. 10 miles to downtown crossing., holiday rental in Winchester

Sweet studio 15 minutes from Bos.Logan Airport. 10 miles to downtown crossing.

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious Studio minutes from Boston, holiday rental in Winchester

Spacious Studio minutes from Boston

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Brand New 4 BR, Free Parking, Near Public Transit, Close to Boston and Cambridge, holiday rental in Winchester

Brand New 4 BR, Free Parking, Near Public Transit, Close to Boston and Cambridge

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Amsden Place, holiday rental in Winchester

Amsden Place

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Luxury Duplex Home close to Boston w/ Driveway Parking & Yard, holiday rental in Winchester

Modern Luxury Duplex Home close to Boston w/ Driveway Parking & Yard

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Malden 3Brm 1Bath 6mileFrom Boston, holiday rental in Winchester

Malden 3Brm 1Bath 6mileFrom Boston

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury Harvard/MIT Victorian w/off street parking., holiday rental in Winchester

Luxury Harvard/MIT Victorian w/off street parking.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Harvard Victorian w/pkng., holiday rental in Winchester

Charming Harvard Victorian w/pkng.

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Big Malden Room Minutes from Train (OU2), holiday rental in Winchester

Big Malden Room Minutes from Train (OU2)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Big Malden Room Minutes to Train (OU1), holiday rental in Winchester

Big Malden Room Minutes to Train (OU1)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Big Private Room Minutes to Train (S2-5), holiday rental in Winchester

Big Private Room Minutes to Train (S2-5)

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Boston Palace Central to Everything, holiday rental in Winchester

Boston Palace Central to Everything

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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*Gorgeous 2 bed / Harvard/MIT/ HLS/ HKS/HBS with cambridge guest parking pass*, holiday rental in Winchester

*Gorgeous 2 bed / Harvard/MIT/ HLS/ HKS/HBS with cambridge guest parking pass*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fellsway 3rd Fl Penthouse Apt - Mins to Boston - Casino - On Bus Route, holiday rental in Winchester

Fellsway 3rd Fl Penthouse Apt - Mins to Boston - Casino - On Bus Route

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Private Room, Boston, Free WiFi, holiday rental in Winchester

Private Room, Boston, Free WiFi

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Big Affordable Room, holiday rental in Winchester

Big Affordable Room

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Comfy Room, Free WiFi, Boston, holiday rental in Winchester

Comfy Room, Free WiFi, Boston

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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BEAUTIFUL FAMILY HOME Great location Boston-Cambridge, holiday rental in Winchester

BEAUTIFUL FAMILY HOME Great location Boston-Cambridge

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Room in Shared Apt (SU1-2), holiday rental in Winchester

Private Room in Shared Apt (SU1-2)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Welcoming & spacious 3bed 2bath entire home!, holiday rental in Winchester

Welcoming & spacious 3bed 2bath entire home!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Harvard  College Campus for one year lease, shorter possible, holiday rental in Winchester

Harvard College Campus for one year lease, shorter possible

3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Located north of Boston/ comfort and relaxation in your home away from home, holiday rental in Winchester

Located north of Boston/ comfort and relaxation in your home away from home

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Large, Furnished Apartment in Cambridge Home, Near Public Transportation, holiday rental in Winchester

Large, Furnished Apartment in Cambridge Home, Near Public Transportation

4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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West Medford Colonial Beauty, Newly Renovated!, holiday rental in Winchester

West Medford Colonial Beauty, Newly Renovated!

3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Private Apartment 2 Room in Everett near Boston near casino

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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TEST PROPERTY-DO NOT BOOK

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Zu Hause weg von zu Hause

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Room in Huge Modern, 4BR Condo (2), holiday rental in Winchester

Room in Huge Modern, 4BR Condo (2)

1 bedroom
1 bathroom
Sleeps 1
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Beautiful Spacious Room (SU1-1), holiday rental in Winchester

Beautiful Spacious Room (SU1-1)

1 bedroom
1 bathroom
Sleeps 1
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Beautiful Spacious Room (SU2-2), holiday rental in Winchester

Beautiful Spacious Room (SU2-2)

1 bedroom
2 bathrooms
Sleeps 1
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Beautiful Spacious Room (S1-3), holiday rental in Winchester

Beautiful Spacious Room (S1-3)

1 bedroom
1 bathroom
Sleeps 1
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One bedroom near Harvard Square, holiday rental in Winchester

One bedroom near Harvard Square

1 bedroom
1 bathroom
Sleeps 1
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