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Winchester Holiday Apartments

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46 rentals in Winchester.
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Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Close to airport, bus & train. 10 min from Boston.  Boston's #10 property., holiday rental in Winchester
Close to airport, bus & train. 10 min from Boston.  Boston's #10 property., holiday rental in Winchester
Close to airport, bus & train. 10 min from Boston.  Boston's #10 property., holiday rental in Winchester

Close to airport, bus & train. 10 min from Boston. Boston's #10 property.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 3 Bdrm - Mins to Tufts, Davis Square, Harvard, holiday rental in Winchester
Luxury 3 Bdrm - Mins to Tufts, Davis Square, Harvard, holiday rental in Winchester
Luxury 3 Bdrm - Mins to Tufts, Davis Square, Harvard, holiday rental in Winchester

Luxury 3 Bdrm - Mins to Tufts, Davis Square, Harvard

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester

Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful renovated 3 bedroom apt near Boston., holiday rental in Winchester
Beautiful renovated 3 bedroom apt near Boston., holiday rental in Winchester
Beautiful renovated 3 bedroom apt near Boston., holiday rental in Winchester

Beautiful renovated 3 bedroom apt near Boston.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Amsden Place (*Tufts, Harvard, MIT), holiday rental in Winchester
Amsden Place (*Tufts, Harvard, MIT), holiday rental in Winchester
Amsden Place (*Tufts, Harvard, MIT), holiday rental in Winchester

Amsden Place (*Tufts, Harvard, MIT)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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, holiday rental in Winchester
A charming modern suburban 3 bedroom condo close to Boston, holiday rental in Winchester

A charming modern suburban 3 bedroom condo close to Boston

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
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, holiday rental in Winchester
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Colonial Two Bedroom Basement Apartment, holiday rental in Winchester
Charming Colonial Two Bedroom Basement Apartment, holiday rental in Winchester
Charming Colonial Two Bedroom Basement Apartment, holiday rental in Winchester

Charming Colonial Two Bedroom Basement Apartment

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Beautiful, holiday rental in Winchester
Beautiful, holiday rental in Winchester
Beautiful, holiday rental in Winchester

Beautiful

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amsden Place, holiday rental in Winchester
Amsden Place, holiday rental in Winchester
Amsden Place, holiday rental in Winchester

Amsden Place

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester

Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spacious Apartment - 5 miles from Boston!, holiday rental in Winchester
Spacious Apartment - 5 miles from Boston!, holiday rental in Winchester
Spacious Apartment - 5 miles from Boston!, holiday rental in Winchester

Spacious Apartment - 5 miles from Boston!

Condo/Apartment
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!, holiday rental in Winchester
West Medford Colonial Beauty, Newly Renovated!, holiday rental in Winchester

West Medford Colonial Beauty, Newly Renovated!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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TEST PROPERTY-DO NOT BOOK

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Home Away From Home

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, holiday rental in Winchester
Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, holiday rental in Winchester
Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts, holiday rental in Winchester

Spend Thanksgiving With Your Family in Historic Lexington, Massachusetts

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private home near amazing downtown Woburn! Sleeps 9, holiday rental in Winchester
Private home near amazing downtown Woburn! Sleeps 9, holiday rental in Winchester
Private home near amazing downtown Woburn! Sleeps 9, holiday rental in Winchester

Private home near amazing downtown Woburn! Sleeps 9

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Beautiful Three Bedroom Condo Near Boston, holiday rental in Winchester
Beautiful Three Bedroom Condo Near Boston, holiday rental in Winchester
Beautiful Three Bedroom Condo Near Boston, holiday rental in Winchester

Beautiful Three Bedroom Condo Near Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vacation Day Is Always a Great Idea! Near Downtown, Liberty Ride Trolley Tour, holiday rental in Winchester
Vacation Day Is Always a Great Idea! Near Downtown, Liberty Ride Trolley Tour, holiday rental in Winchester
Vacation Day Is Always a Great Idea! Near Downtown, Liberty Ride Trolley Tour, holiday rental in Winchester

Vacation Day Is Always a Great Idea! Near Downtown, Liberty Ride Trolley Tour

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dream Family Vacation! 2 Pet-Friendly Units, Close to Liberty Ride Trolley Tour!, holiday rental in Winchester
Dream Family Vacation! 2 Pet-Friendly Units, Close to Liberty Ride Trolley Tour!, holiday rental in Winchester
Dream Family Vacation! 2 Pet-Friendly Units, Close to Liberty Ride Trolley Tour!, holiday rental in Winchester

Dream Family Vacation! 2 Pet-Friendly Units, Close to Liberty Ride Trolley Tour!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Unique loft style garden level studio apartment, holiday rental in Winchester
Unique loft style garden level studio apartment, holiday rental in Winchester
Unique loft style garden level studio apartment, holiday rental in Winchester

Unique loft style garden level studio apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New Single Family 5b/3b with Central AC, holiday rental in Winchester
New Single Family 5b/3b with Central AC, holiday rental in Winchester
New Single Family 5b/3b with Central AC, holiday rental in Winchester

New Single Family 5b/3b with Central AC

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Perfect Family Escape! 3 Great Units, FREE Parking, Close to Stone Zoo!, holiday rental in Winchester
The Perfect Family Escape! 3 Great Units, FREE Parking, Close to Stone Zoo!, holiday rental in Winchester
The Perfect Family Escape! 3 Great Units, FREE Parking, Close to Stone Zoo!, holiday rental in Winchester

The Perfect Family Escape! 3 Great Units, FREE Parking, Close to Stone Zoo!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Starts Here! 2 Comfortable Units, Pets Allowed, Steps to Woburn Mall!, holiday rental in Winchester
Vacation Starts Here! 2 Comfortable Units, Pets Allowed, Steps to Woburn Mall!, holiday rental in Winchester
Vacation Starts Here! 2 Comfortable Units, Pets Allowed, Steps to Woburn Mall!, holiday rental in Winchester

Vacation Starts Here! 2 Comfortable Units, Pets Allowed, Steps to Woburn Mall!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Great Find! 3 Budget-Friendly Units! Pet-Friendly, Minutes to Stone Zoo!, holiday rental in Winchester
Great Find! 3 Budget-Friendly Units! Pet-Friendly, Minutes to Stone Zoo!, holiday rental in Winchester
Great Find! 3 Budget-Friendly Units! Pet-Friendly, Minutes to Stone Zoo!, holiday rental in Winchester

Great Find! 3 Budget-Friendly Units! Pet-Friendly, Minutes to Stone Zoo!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet and spacious 2 floor-3 bedroom condo, holiday rental in Winchester
Quiet and spacious 2 floor-3 bedroom condo, holiday rental in Winchester
Quiet and spacious 2 floor-3 bedroom condo, holiday rental in Winchester

Quiet and spacious 2 floor-3 bedroom condo

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, holiday rental in Winchester
Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, holiday rental in Winchester
Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults, holiday rental in Winchester

Beautifully furnished 3 bedrooms close to Boston Apt up to 5 adults

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2 Comfortable Units, FREE Parking, Closet to Old Ship Street Historic District!, holiday rental in Winchester
2 Comfortable Units, FREE Parking, Closet to Old Ship Street Historic District!, holiday rental in Winchester
2 Comfortable Units, FREE Parking, Closet to Old Ship Street Historic District!, holiday rental in Winchester

2 Comfortable Units, FREE Parking, Closet to Old Ship Street Historic District!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pets Stay Free! 2 Family-Friendly Units, FREE Parking, Minutes to Stone Zoo!, holiday rental in Winchester
Pets Stay Free! 2 Family-Friendly Units, FREE Parking, Minutes to Stone Zoo!, holiday rental in Winchester
Pets Stay Free! 2 Family-Friendly Units, FREE Parking, Minutes to Stone Zoo!, holiday rental in Winchester

Pets Stay Free! 2 Family-Friendly Units, FREE Parking, Minutes to Stone Zoo!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Boston Adventure! 3 Family-Friendly Units, Minutes to Liberty Ride Trolley Tour!, holiday rental in Winchester
Boston Adventure! 3 Family-Friendly Units, Minutes to Liberty Ride Trolley Tour!, holiday rental in Winchester
Boston Adventure! 3 Family-Friendly Units, Minutes to Liberty Ride Trolley Tour!, holiday rental in Winchester

Boston Adventure! 3 Family-Friendly Units, Minutes to Liberty Ride Trolley Tour!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Family & Friends Getaway! 3 Great Units, FREE Parking,. Steps to Woburn Mall!, holiday rental in Winchester
Family & Friends Getaway! 3 Great Units, FREE Parking,. Steps to Woburn Mall!, holiday rental in Winchester
Family & Friends Getaway! 3 Great Units, FREE Parking,. Steps to Woburn Mall!, holiday rental in Winchester

Family & Friends Getaway! 3 Great Units, FREE Parking,. Steps to Woburn Mall!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Take An Amazing Vacation! 2 Great Units, FREE Parking, Near Medford Square!, holiday rental in Winchester
Take An Amazing Vacation! 2 Great Units, FREE Parking, Near Medford Square!, holiday rental in Winchester
Take An Amazing Vacation! 2 Great Units, FREE Parking, Near Medford Square!, holiday rental in Winchester

Take An Amazing Vacation! 2 Great Units, FREE Parking, Near Medford Square!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Easy Highway Access! Pet-Friendly Property, Short Drive to Medford Square!, holiday rental in Winchester
Easy Highway Access! Pet-Friendly Property, Short Drive to Medford Square!, holiday rental in Winchester
Easy Highway Access! Pet-Friendly Property, Short Drive to Medford Square!, holiday rental in Winchester

Easy Highway Access! Pet-Friendly Property, Short Drive to Medford Square!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boston Adventure! Pets Allowed, FREE Parking, Near Liberty Ride Trolley Tour!, holiday rental in Winchester
Boston Adventure! Pets Allowed, FREE Parking, Near Liberty Ride Trolley Tour!, holiday rental in Winchester
Boston Adventure! Pets Allowed, FREE Parking, Near Liberty Ride Trolley Tour!, holiday rental in Winchester

Boston Adventure! Pets Allowed, FREE Parking, Near Liberty Ride Trolley Tour!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Getaway with Friends! FREE Parking, Minutes to Downtown Boston and Woburn Mall!, holiday rental in Winchester
Getaway with Friends! FREE Parking, Minutes to Downtown Boston and Woburn Mall!, holiday rental in Winchester
Getaway with Friends! FREE Parking, Minutes to Downtown Boston and Woburn Mall!, holiday rental in Winchester

Getaway with Friends! FREE Parking, Minutes to Downtown Boston and Woburn Mall!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Prime Location! 3 Comfortable Units, FREE Parking, Close to Woburn Mall, holiday rental in Winchester
Prime Location! 3 Comfortable Units, FREE Parking, Close to Woburn Mall, holiday rental in Winchester
Prime Location! 3 Comfortable Units, FREE Parking, Close to Woburn Mall, holiday rental in Winchester

Prime Location! 3 Comfortable Units, FREE Parking, Close to Woburn Mall

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Easy Highway Access! 3 Family-Friendly Property, Pets Allowed, Near Woburn Mall!, holiday rental in Winchester
Easy Highway Access! 3 Family-Friendly Property, Pets Allowed, Near Woburn Mall!, holiday rental in Winchester
Easy Highway Access! 3 Family-Friendly Property, Pets Allowed, Near Woburn Mall!, holiday rental in Winchester

Easy Highway Access! 3 Family-Friendly Property, Pets Allowed, Near Woburn Mall!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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2 Budget-Friendly Units! Pets Allowed, Just Minutes From The Ottawa River!, holiday rental in Winchester
2 Budget-Friendly Units! Pets Allowed, Just Minutes From The Ottawa River!, holiday rental in Winchester
2 Budget-Friendly Units! Pets Allowed, Just Minutes From The Ottawa River!, holiday rental in Winchester

2 Budget-Friendly Units! Pets Allowed, Just Minutes From The Ottawa River!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Two Bedroom Condo Near Boston, holiday rental in Winchester
Beautiful Two Bedroom Condo Near Boston, holiday rental in Winchester
Beautiful Two Bedroom Condo Near Boston, holiday rental in Winchester

Beautiful Two Bedroom Condo Near Boston

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vacation Starts Here! Pets Allowed and FREE Parking, Steps to Woburn Mall!, holiday rental in Winchester
Vacation Starts Here! Pets Allowed and FREE Parking, Steps to Woburn Mall!, holiday rental in Winchester
Vacation Starts Here! Pets Allowed and FREE Parking, Steps to Woburn Mall!, holiday rental in Winchester

Vacation Starts Here! Pets Allowed and FREE Parking, Steps to Woburn Mall!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Melrose two bedroomer, holiday rental in Winchester
Melrose two bedroomer, holiday rental in Winchester
Melrose two bedroomer, holiday rental in Winchester

Melrose two bedroomer

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sphisticated, bright, and cheerful 2 story home, holiday rental in Winchester
Sphisticated, bright, and cheerful 2 story home, holiday rental in Winchester
Sphisticated, bright, and cheerful 2 story home, holiday rental in Winchester

Sphisticated, bright, and cheerful 2 story home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Boston area house & gardens, near parks, farms, woods trails, shops, buses, holiday rental in Winchester
Boston area house & gardens, near parks, farms, woods trails, shops, buses, holiday rental in Winchester
Boston area house & gardens, near parks, farms, woods trails, shops, buses, holiday rental in Winchester

Boston area house & gardens, near parks, farms, woods trails, shops, buses

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Clean apartment - 5 miles from Boston, holiday rental in Winchester
Clean apartment - 5 miles from Boston, holiday rental in Winchester
Clean apartment - 5 miles from Boston, holiday rental in Winchester

Clean apartment - 5 miles from Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Malden West End Apartment close to Boston, holiday rental in Winchester
Malden West End Apartment close to Boston, holiday rental in Winchester
Malden West End Apartment close to Boston, holiday rental in Winchester

Malden West End Apartment close to Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Davis Square Magnificent Room, Semiprivate Bath, holiday rental in Winchester
Davis Square Magnificent Room, Semiprivate Bath, holiday rental in Winchester
Davis Square Magnificent Room, Semiprivate Bath, holiday rental in Winchester

Davis Square Magnificent Room, Semiprivate Bath

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
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Large room walk to T --15' drive to MIT, holiday rental in Winchester
Large room walk to T --15' drive to MIT, holiday rental in Winchester
Large room walk to T --15' drive to MIT, holiday rental in Winchester

Large room walk to T --15' drive to MIT

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 1
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Small room close T for noon smoking, one person only, holiday rental in Winchester
Small room close T for noon smoking, one person only, holiday rental in Winchester
Small room close T for noon smoking, one person only, holiday rental in Winchester

Small room close T for noon smoking, one person only

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 1
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Room G, Large room for rent ---15' drive to MIT, holiday rental in Winchester
Room G, Large room for rent ---15' drive to MIT, holiday rental in Winchester
Room G, Large room for rent ---15' drive to MIT, holiday rental in Winchester

Room G, Large room for rent ---15' drive to MIT

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 1
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