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Winthrop Vacation Rentals

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49 rentals in Winthrop.
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Luxury, New 2-Bedroom Condo Near Airport/Boston/Train, vacation rental in Winthrop
Luxury, New 2-Bedroom Condo Near Airport/Boston/Train, vacation rental in Winthrop
Luxury, New 2-Bedroom Condo Near Airport/Boston/Train, vacation rental in Winthrop

Luxury, New 2-Bedroom Condo Near Airport/Boston/Train

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Casa de Los Clarey Boston Airport Beaches Off Street Parking Available, vacation rental in Winthrop
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available, vacation rental in Winthrop
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available, vacation rental in Winthrop

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Boston Harbor One or Two Bedroom Waterfront Home, vacation rental in Winthrop
Boston Harbor One or Two Bedroom Waterfront Home, vacation rental in Winthrop
Boston Harbor One or Two Bedroom Waterfront Home, vacation rental in Winthrop

Boston Harbor One or Two Bedroom Waterfront Home

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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King Studio, vacation rental in Winthrop
King Studio, vacation rental in Winthrop
King Studio, vacation rental in Winthrop

King Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Queen One Bedroom Suite, vacation rental in Winthrop
Queen One Bedroom Suite, vacation rental in Winthrop
Queen One Bedroom Suite, vacation rental in Winthrop

Queen One Bedroom Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront One or Two Bedroom Private Apartment on Boston Harbor, vacation rental in Winthrop
Waterfront One or Two Bedroom Private Apartment on Boston Harbor, vacation rental in Winthrop
Waterfront One or Two Bedroom Private Apartment on Boston Harbor, vacation rental in Winthrop

Waterfront One or Two Bedroom Private Apartment on Boston Harbor

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Vibrant Winthrop Apartment - Close to Ocean!, vacation rental in Winthrop
NEW! Vibrant Winthrop Apartment - Close to Ocean!, vacation rental in Winthrop
NEW! Vibrant Winthrop Apartment - Close to Ocean!, vacation rental in Winthrop

NEW! Vibrant Winthrop Apartment - Close to Ocean!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Sublet on marina! Close to downtown Boston/Airport, vacation rental in Winthrop
Gorgeous Sublet on marina! Close to downtown Boston/Airport, vacation rental in Winthrop
Gorgeous Sublet on marina! Close to downtown Boston/Airport, vacation rental in Winthrop

Gorgeous Sublet on marina! Close to downtown Boston/Airport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
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Ikram's Place so close to Boston, Subway & Logan international Airport, vacation rental in Winthrop
Ikram's Place so close to Boston, Subway & Logan international Airport, vacation rental in Winthrop
Ikram's Place so close to Boston, Subway & Logan international Airport, vacation rental in Winthrop

Ikram's Place so close to Boston, Subway & Logan international Airport

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cape Cod style Oceanside cottage, Boston,train,plane,refresh,new linens & towels, vacation rental in Winthrop
Cape Cod style Oceanside cottage, Boston,train,plane,refresh,new linens & towels, vacation rental in Winthrop
Cape Cod style Oceanside cottage, Boston,train,plane,refresh,new linens & towels, vacation rental in Winthrop

Cape Cod style Oceanside cottage, Boston,train,plane,refresh,new linens & towels

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, vacation rental in Winthrop
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, vacation rental in Winthrop
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, vacation rental in Winthrop

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., vacation rental in Winthrop
2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., vacation rental in Winthrop
2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., vacation rental in Winthrop

2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions.

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy/warm Near-Commuter rail, Boston, Airport, Casino and More !

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, vacation rental in Winthrop
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, vacation rental in Winthrop
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, vacation rental in Winthrop

Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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*** Open-Plan Luxury Condo / Close To Logan Airport***, vacation rental in Winthrop
*** Open-Plan Luxury Condo / Close To Logan Airport***, vacation rental in Winthrop
*** Open-Plan Luxury Condo / Close To Logan Airport***, vacation rental in Winthrop

*** Open-Plan Luxury Condo / Close To Logan Airport***

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern Beachside Space - Near Boston/Airport/Train, vacation rental in Winthrop
Modern Beachside Space - Near Boston/Airport/Train, vacation rental in Winthrop
Modern Beachside Space - Near Boston/Airport/Train, vacation rental in Winthrop

Modern Beachside Space - Near Boston/Airport/Train

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 2BR condo king size bed fireplace and  free parking 420 friendly, vacation rental in Winthrop
Spacious 2BR condo king size bed fireplace and  free parking 420 friendly, vacation rental in Winthrop
Spacious 2BR condo king size bed fireplace and  free parking 420 friendly, vacation rental in Winthrop

Spacious 2BR condo king size bed fireplace and free parking 420 friendly

Rental Home
5 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, vacation rental in Winthrop
Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, vacation rental in Winthrop
Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, vacation rental in Winthrop

Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston

Condo/Apartment in Eagle Hill
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Modern 2 Bedrooms Apartment Close to Boston, vacation rental in Winthrop
Cozy Modern 2 Bedrooms Apartment Close to Boston, vacation rental in Winthrop
Cozy Modern 2 Bedrooms Apartment Close to Boston, vacation rental in Winthrop

Cozy Modern 2 Bedrooms Apartment Close to Boston

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport, vacation rental in Winthrop
Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport, vacation rental in Winthrop
Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport, vacation rental in Winthrop

Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Apartment 10 min to Airport and city, vacation rental in Winthrop
Cozy Apartment 10 min to Airport and city, vacation rental in Winthrop
Cozy Apartment 10 min to Airport and city, vacation rental in Winthrop

Cozy Apartment 10 min to Airport and city

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Enisa's Home - Boston/Airport/Walk to t-line & beach!, vacation rental in Winthrop
Enisa's Home - Boston/Airport/Walk to t-line & beach!, vacation rental in Winthrop
Enisa's Home - Boston/Airport/Walk to t-line & beach!, vacation rental in Winthrop

Enisa's Home - Boston/Airport/Walk to t-line & beach!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Brand new beach unit ����♂️⛵�️, vacation rental in Winthrop
Brand new beach unit ����♂️⛵�️, vacation rental in Winthrop
Brand new beach unit ����♂️⛵�️, vacation rental in Winthrop

Brand new beach unit ����♂️⛵�️

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nice 3 Bed Apt near Downtown Boston, vacation rental in Winthrop
Nice 3 Bed Apt near Downtown Boston, vacation rental in Winthrop
Nice 3 Bed Apt near Downtown Boston, vacation rental in Winthrop

Nice 3 Bed Apt near Downtown Boston

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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1 bedroom apt.Minutes to Encore Casino and Boston., vacation rental in Winthrop
1 bedroom apt.Minutes to Encore Casino and Boston., vacation rental in Winthrop
1 bedroom apt.Minutes to Encore Casino and Boston., vacation rental in Winthrop

1 bedroom apt.Minutes to Encore Casino and Boston.

Rental Home
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Mujan's home away from home, vacation rental in Winthrop
Mujan's home away from home, vacation rental in Winthrop
Mujan's home away from home, vacation rental in Winthrop

Mujan's home away from home

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop
Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop
Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop

Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water, vacation rental in Winthrop
43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water, vacation rental in Winthrop
43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water, vacation rental in Winthrop

43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , vacation rental in Winthrop
Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , vacation rental in Winthrop
Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , vacation rental in Winthrop

Fully Furnished Modern Condo Close to all Amenities, Restaurants Free parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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2B Clark Chelsea - Boston, vacation rental in Winthrop
2B Clark Chelsea - Boston, vacation rental in Winthrop
2B Clark Chelsea - Boston, vacation rental in Winthrop

2B Clark Chelsea - Boston

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Room In The House Right Across First Public American Revere Beach And Ocean, vacation rental in Winthrop
Cozy Room In The House Right Across First Public American Revere Beach And Ocean, vacation rental in Winthrop
Cozy Room In The House Right Across First Public American Revere Beach And Ocean, vacation rental in Winthrop

Cozy Room In The House Right Across First Public American Revere Beach And Ocean

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cheerful House with 2 Large Bedrooms, vacation rental in Winthrop
Cheerful House with 2 Large Bedrooms, vacation rental in Winthrop
Cheerful House with 2 Large Bedrooms, vacation rental in Winthrop

Cheerful House with 2 Large Bedrooms

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pet-Friendly Revere Getaway, Steps from the T!, vacation rental in Winthrop
Pet-Friendly Revere Getaway, Steps from the T!, vacation rental in Winthrop
Pet-Friendly Revere Getaway, Steps from the T!, vacation rental in Winthrop

Pet-Friendly Revere Getaway, Steps from the T!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Pet-Friendly Apartment, 6 Miles to Downtown, vacation rental in Winthrop
NEW! Pet-Friendly Apartment, 6 Miles to Downtown, vacation rental in Winthrop
NEW! Pet-Friendly Apartment, 6 Miles to Downtown, vacation rental in Winthrop

NEW! Pet-Friendly Apartment, 6 Miles to Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Boston Apartment, < 10 Mi to Top Universities, vacation rental in Winthrop
NEW! Boston Apartment, < 10 Mi to Top Universities, vacation rental in Winthrop
NEW! Boston Apartment, < 10 Mi to Top Universities, vacation rental in Winthrop

NEW! Boston Apartment, < 10 Mi to Top Universities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop
Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop
Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas, vacation rental in Winthrop

Suite at House of L: Beautiful Garden, AC, Fast WiFi, near Boston, Eateries, Cas

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Cozy apartment-close to Logan/Revere Beach/Downtown Boston, vacation rental in Winthrop
Amazing Cozy apartment-close to Logan/Revere Beach/Downtown Boston, vacation rental in Winthrop
Amazing Cozy apartment-close to Logan/Revere Beach/Downtown Boston, vacation rental in Winthrop

Amazing Cozy apartment-close to Logan/Revere Beach/Downtown Boston

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful apartment in the best location., vacation rental in Winthrop
Beautiful apartment in the best location., vacation rental in Winthrop
Beautiful apartment in the best location., vacation rental in Winthrop

Beautiful apartment in the best location.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Convenience at Conant! Home Away From Home For 5+!, vacation rental in Winthrop
Convenience at Conant! Home Away From Home For 5+!, vacation rental in Winthrop
Convenience at Conant! Home Away From Home For 5+!, vacation rental in Winthrop

Convenience at Conant! Home Away From Home For 5+!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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4 BR 4000 SF OCEANFRONT MODERN HOME NR BEACH, DOWNTOWN, AIRPORT - 90 DAY MINIMUM, vacation rental in Winthrop
4 BR 4000 SF OCEANFRONT MODERN HOME NR BEACH, DOWNTOWN, AIRPORT - 90 DAY MINIMUM, vacation rental in Winthrop
4 BR 4000 SF OCEANFRONT MODERN HOME NR BEACH, DOWNTOWN, AIRPORT - 90 DAY MINIMUM, vacation rental in Winthrop

4 BR 4000 SF OCEANFRONT MODERN HOME NR BEACH, DOWNTOWN, AIRPORT - 90 DAY MINIMUM

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Room With Part Ocean View! First Public Revere Beach Right Across The House, vacation rental in Winthrop
Cozy Room With Part Ocean View! First Public Revere Beach Right Across The House, vacation rental in Winthrop
Cozy Room With Part Ocean View! First Public Revere Beach Right Across The House, vacation rental in Winthrop

Cozy Room With Part Ocean View! First Public Revere Beach Right Across The House

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern 2/Bed 2/Bath Condo near Boston # W/Parking, vacation rental in Winthrop
Modern 2/Bed 2/Bath Condo near Boston # W/Parking, vacation rental in Winthrop
Modern 2/Bed 2/Bath Condo near Boston # W/Parking, vacation rental in Winthrop

Modern 2/Bed 2/Bath Condo near Boston # W/Parking

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2BR with a king size bed and TV and  all the amenities you need, vacation rental in Winthrop
2BR with a king size bed and TV and  all the amenities you need, vacation rental in Winthrop
2BR with a king size bed and TV and  all the amenities you need, vacation rental in Winthrop

2BR with a king size bed and TV and all the amenities you need

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ocean View & City View, vacation rental in Winthrop
Ocean View & City View, vacation rental in Winthrop
Ocean View & City View, vacation rental in Winthrop

Ocean View & City View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 30
Match: Sleeps
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Luxury 2 BR | 2BA on Revere Beach, vacation rental in Winthrop
Luxury 2 BR | 2BA on Revere Beach, vacation rental in Winthrop
Luxury 2 BR | 2BA on Revere Beach, vacation rental in Winthrop

Luxury 2 BR | 2BA on Revere Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Luxury 1 BR | 1 BA w/ Office Room on Revere Beach, vacation rental in Winthrop
Luxury 1 BR | 1 BA w/ Office Room on Revere Beach, vacation rental in Winthrop
Luxury 1 BR | 1 BA w/ Office Room on Revere Beach, vacation rental in Winthrop

Luxury 1 BR | 1 BA w/ Office Room on Revere Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Modern 3BR with free parking near Revere Beach!!, vacation rental in Winthrop
Modern 3BR with free parking near Revere Beach!!, vacation rental in Winthrop
Modern 3BR with free parking near Revere Beach!!, vacation rental in Winthrop

Modern 3BR with free parking near Revere Beach!!

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Everything You Need, Bright Sunny Condo, vacation rental in Winthrop
Everything You Need, Bright Sunny Condo, vacation rental in Winthrop
Everything You Need, Bright Sunny Condo, vacation rental in Winthrop

Everything You Need, Bright Sunny Condo

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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1 minute walk to subway, 10 minutes to  airport, vacation rental in Winthrop
1 minute walk to subway, 10 minutes to  airport, vacation rental in Winthrop
1 minute walk to subway, 10 minutes to  airport, vacation rental in Winthrop

1 minute walk to subway, 10 minutes to airport

Private Room
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston, vacation rental in Winthrop
Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston, vacation rental in Winthrop
Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston, vacation rental in Winthrop

Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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