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Winthrop Holiday Apartments

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48 rentals in Winthrop.
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Boston Harbor One or Two Bedroom Waterfront Home, holiday rental in Winthrop
Boston Harbor One or Two Bedroom Waterfront Home, holiday rental in Winthrop
Boston Harbor One or Two Bedroom Waterfront Home, holiday 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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Queen One Bedroom Suite, holiday rental in Winthrop
Queen One Bedroom Suite, holiday rental in Winthrop
Queen One Bedroom Suite, holiday rental in Winthrop

Queen One Bedroom Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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King Studio, holiday rental in Winthrop
King Studio, holiday rental in Winthrop
King Studio, holiday rental in Winthrop

King Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront One or Two Bedroom Private Apartment on Boston Harbor, holiday rental in Winthrop
Waterfront One or Two Bedroom Private Apartment on Boston Harbor, holiday rental in Winthrop
Waterfront One or Two Bedroom Private Apartment on Boston Harbor, holiday rental in Winthrop

Waterfront One or Two Bedroom Private Apartment on Boston Harbor

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ikram's Place so close to Boston, Subway & Logan international Airport, holiday rental in Winthrop
Ikram's Place so close to Boston, Subway & Logan international Airport, holiday rental in Winthrop
Ikram's Place so close to Boston, Subway & Logan international Airport, holiday 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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Fun, Family Friendly Restored Fire House 2 Bedroom Apt, holiday rental in Winthrop
Fun, Family Friendly Restored Fire House 2 Bedroom Apt, holiday rental in Winthrop
Fun, Family Friendly Restored Fire House 2 Bedroom Apt, holiday rental in Winthrop

Fun, Family Friendly Restored Fire House 2 Bedroom Apt

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming New England cottage within walking distance to three beaches., holiday rental in Winthrop
Charming New England cottage within walking distance to three beaches., holiday rental in Winthrop
Charming New England cottage within walking distance to three beaches., holiday rental in Winthrop

Charming New England cottage within walking distance to three beaches.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Seaside Oasis in Nahant, holiday rental in Winthrop
Seaside Oasis in Nahant, holiday rental in Winthrop
Seaside Oasis in Nahant, holiday rental in Winthrop

Seaside Oasis in Nahant

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 BR/ 3 BATH in Historic Home Mins from Kendall Sq , MIT,  Harvard, Boston..., holiday rental in Winthrop
3 BR/ 3 BATH in Historic Home Mins from Kendall Sq , MIT,  Harvard, Boston..., holiday rental in Winthrop
3 BR/ 3 BATH in Historic Home Mins from Kendall Sq , MIT,  Harvard, Boston..., holiday rental in Winthrop

3 BR/ 3 BATH in Historic Home Mins from Kendall Sq , MIT, Harvard, Boston...

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront vacation home w/ private beach and spectacular views on the Atlantic

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Newly renovated home, top of the line appliances., holiday rental in Winthrop
Newly renovated home, top of the line appliances., holiday rental in Winthrop
Newly renovated home, top of the line appliances., holiday rental in Winthrop

Newly renovated home, top of the line appliances.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cape Cod Oceanside cottage, nr. Boston,train,plane, adhere to CDC, c-19 retreat, holiday rental in Winthrop
Cape Cod Oceanside cottage, nr. Boston,train,plane, adhere to CDC, c-19 retreat, holiday rental in Winthrop
Cape Cod Oceanside cottage, nr. Boston,train,plane, adhere to CDC, c-19 retreat, holiday rental in Winthrop

Cape Cod Oceanside cottage, nr. Boston,train,plane, adhere to CDC, c-19 retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular OCEANFRONT near BOSTON, SALEM and Logan Airport, holiday rental in Winthrop
Spectacular OCEANFRONT near BOSTON, SALEM and Logan Airport, holiday rental in Winthrop
Spectacular OCEANFRONT near BOSTON, SALEM and Logan Airport, holiday rental in Winthrop

Spectacular OCEANFRONT near BOSTON, SALEM and Logan Airport

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Unobstructed Direct Oceanfront  in Seaside Boston/Nahant, holiday rental in Winthrop
Unobstructed Direct Oceanfront  in Seaside Boston/Nahant, holiday rental in Winthrop
Unobstructed Direct Oceanfront  in Seaside Boston/Nahant, holiday rental in Winthrop

Unobstructed Direct Oceanfront in Seaside Boston/Nahant

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., holiday rental in Winthrop
2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., holiday rental in Winthrop
2 Bedroom Home Minutes to Boston, Logan, TD Garden, and all Attractions., holiday rental in Winthrop

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Boston (4 miles) | Clean | Safe | Family | NO PARTIES | Near Train/Bus, holiday rental in Winthrop
Boston (4 miles) | Clean | Safe | Family | NO PARTIES | Near Train/Bus, holiday rental in Winthrop
Boston (4 miles) | Clean | Safe | Family | NO PARTIES | Near Train/Bus, holiday rental in Winthrop

Boston (4 miles) | Clean | Safe | Family | NO PARTIES | Near Train/Bus

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
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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NEW! Cozy Boston Area Home < 1 Mi to Revere Beach!, holiday rental in Winthrop
NEW! Cozy Boston Area Home < 1 Mi to Revere Beach!, holiday rental in Winthrop
NEW! Cozy Boston Area Home < 1 Mi to Revere Beach!, holiday rental in Winthrop

NEW! Cozy Boston Area Home < 1 Mi to Revere Beach!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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★ Modern-Gem w/ Parking - 1.5m to Encore Casino ♣︎, holiday rental in Winthrop
★ Modern-Gem w/ Parking - 1.5m to Encore Casino ♣︎, holiday rental in Winthrop
★ Modern-Gem w/ Parking - 1.5m to Encore Casino ♣︎, holiday rental in Winthrop

★ Modern-Gem w/ Parking - 1.5m to Encore Casino ♣︎

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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*** Open-Plan Luxury Condo / Close To Logan Airport***, holiday rental in Winthrop
*** Open-Plan Luxury Condo / Close To Logan Airport***, holiday rental in Winthrop
*** Open-Plan Luxury Condo / Close To Logan Airport***, holiday rental in Winthrop

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern 3BR/ Free Parking Close to Encore- Everett #2, holiday rental in Winthrop
Modern 3BR/ Free Parking Close to Encore- Everett #2, holiday rental in Winthrop
Modern 3BR/ Free Parking Close to Encore- Everett #2, holiday rental in Winthrop

Modern 3BR/ Free Parking Close to Encore- Everett #2

Condo/Apartment
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, holiday rental in Winthrop
Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, holiday rental in Winthrop
Entire Private 2Bd Apartment/Condo Near Airport Blue Line Train Station Boston, holiday 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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Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, holiday rental in Winthrop
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, holiday rental in Winthrop
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!, holiday 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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Cozy Modern 2 Bedrooms Apartment Close to Boston, holiday rental in Winthrop
Cozy Modern 2 Bedrooms Apartment Close to Boston, holiday rental in Winthrop
Cozy Modern 2 Bedrooms Apartment Close to Boston, holiday rental in Winthrop

Cozy Modern 2 Bedrooms Apartment Close to Boston

Holiday Rental House
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, holiday rental in Winthrop
Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport, holiday rental in Winthrop
Stunning 1 BR-Apt-Oceanview to Revere Beach -3 Train Stop Boston Logan Airport, holiday 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, holiday rental in Winthrop
Cozy Apartment 10 min to Airport and city, holiday rental in Winthrop
Cozy Apartment 10 min to Airport and city, holiday 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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Modern 3BR/ Close to Encore & Boston- Everett #3, holiday rental in Winthrop
Modern 3BR/ Close to Encore & Boston- Everett #3, holiday rental in Winthrop
Modern 3BR/ Close to Encore & Boston- Everett #3, holiday rental in Winthrop

Modern 3BR/ Close to Encore & Boston- Everett #3

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Large spacious 6 bedroom house, holiday rental in Winthrop
Large spacious 6 bedroom house, holiday rental in Winthrop
Large spacious 6 bedroom house, holiday rental in Winthrop

Large spacious 6 bedroom house

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Modern Beachside Space - Near Boston/Airport/Train, holiday rental in Winthrop
Modern Beachside Space - Near Boston/Airport/Train, holiday rental in Winthrop
Modern Beachside Space - Near Boston/Airport/Train, holiday rental in Winthrop

Modern Beachside Space - Near Boston/Airport/Train

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stay in Style! The Encore Suite + Free parking!, holiday rental in Winthrop
Stay in Style! The Encore Suite + Free parking!, holiday rental in Winthrop
Stay in Style! The Encore Suite + Free parking!, holiday rental in Winthrop

Stay in Style! The Encore Suite + Free parking!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Ranch Home, holiday rental in Winthrop
Beautiful Ranch Home, holiday rental in Winthrop
Beautiful Ranch Home, holiday rental in Winthrop

Beautiful Ranch Home

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Enisa's Home - Boston/Airport/Walk to t-line & beach!, holiday rental in Winthrop
Enisa's Home - Boston/Airport/Walk to t-line & beach!, holiday rental in Winthrop
Enisa's Home - Boston/Airport/Walk to t-line & beach!, holiday rental in Winthrop

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

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Brand new house apartment for VIP        -, holiday rental in Winthrop
Brand new house apartment for VIP        -, holiday rental in Winthrop
Brand new house apartment for VIP        -, holiday rental in Winthrop

Brand new house apartment for VIP -

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nice 3 Bed Apt near Downtown Boston, holiday rental in Winthrop
Nice 3 Bed Apt near Downtown Boston, holiday rental in Winthrop
Nice 3 Bed Apt near Downtown Boston, holiday rental in Winthrop

Nice 3 Bed Apt near Downtown Boston

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

1 bedroom apt.Minutes to Encore Casino and Boston.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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10 Min To Boston Casino 15 Min To The Garden & Downtown 20 Min Frm Logan Airport, holiday rental in Winthrop
10 Min To Boston Casino 15 Min To The Garden & Downtown 20 Min Frm Logan Airport, holiday rental in Winthrop
10 Min To Boston Casino 15 Min To The Garden & Downtown 20 Min Frm Logan Airport, holiday rental in Winthrop

10 Min To Boston Casino 15 Min To The Garden & Downtown 20 Min Frm Logan Airport

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Sanitized Oasis, Clean & Modern Escape Near Boston’s New Casino & Airport, holiday rental in Winthrop
Sanitized Oasis, Clean & Modern Escape Near Boston’s New Casino & Airport, holiday rental in Winthrop
Sanitized Oasis, Clean & Modern Escape Near Boston’s New Casino & Airport, holiday rental in Winthrop

Sanitized Oasis, Clean & Modern Escape Near Boston’s New Casino & Airport

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Private + Clean 1BR | Kitchen | Work Desk+WiFi | Kendall Square, holiday rental in Winthrop
Private + Clean 1BR | Kitchen | Work Desk+WiFi | Kendall Square, holiday rental in Winthrop
Private + Clean 1BR | Kitchen | Work Desk+WiFi | Kendall Square, holiday rental in Winthrop

Private + Clean 1BR | Kitchen | Work Desk+WiFi | Kendall Square

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Boston (4 miles) | Clean | Safe | WIFI | FAMILY | NO PARTIES, holiday rental in Winthrop
Boston (4 miles) | Clean | Safe | WIFI | FAMILY | NO PARTIES, holiday rental in Winthrop
Boston (4 miles) | Clean | Safe | WIFI | FAMILY | NO PARTIES, holiday rental in Winthrop

Boston (4 miles) | Clean | Safe | WIFI | FAMILY | NO PARTIES

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mod Kendall Square 1BR w/ W/D, near Mass General Hospital, holiday rental in Winthrop
Mod Kendall Square 1BR w/ W/D, near Mass General Hospital, holiday rental in Winthrop
Mod Kendall Square 1BR w/ W/D, near Mass General Hospital, holiday rental in Winthrop

Mod Kendall Square 1BR w/ W/D, near Mass General Hospital

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mujan's home away from home, holiday rental in Winthrop
Mujan's home away from home, holiday rental in Winthrop
Mujan's home away from home, holiday rental in Winthrop

Mujan's home away from home

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New! Renovated Private Apartment near Boston, Eateries, Encore Casino, Mass Gene, holiday rental in Winthrop
New! Renovated Private Apartment near Boston, Eateries, Encore Casino, Mass Gene, holiday rental in Winthrop
New! Renovated Private Apartment near Boston, Eateries, Encore Casino, Mass Gene, holiday rental in Winthrop

New! Renovated Private Apartment near Boston, Eateries, Encore Casino, Mass Gene

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, holiday rental in Winthrop
43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water, holiday rental in Winthrop
43' Boston Harbor Motor Yacht - Walk to North End and Relax on the Water, holiday rental in Winthrop

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing Location in Little Italy with Roof Deck, holiday rental in Winthrop
Amazing Location in Little Italy with Roof Deck, holiday rental in Winthrop
Amazing Location in Little Italy with Roof Deck, holiday rental in Winthrop

Amazing Location in Little Italy with Roof Deck

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , holiday rental in Winthrop
Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , holiday rental in Winthrop
Fully Furnished Modern Condo Close to all Amenities, Restaurants  Free parking  , holiday 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, holiday rental in Winthrop
2B Clark Chelsea - Boston, holiday rental in Winthrop
2B Clark Chelsea - Boston, holiday rental in Winthrop

2B Clark Chelsea - Boston

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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1 minute walk to subway, 10 minutes to  airport, holiday rental in Winthrop
1 minute walk to subway, 10 minutes to  airport, holiday rental in Winthrop
1 minute walk to subway, 10 minutes to  airport, holiday 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, holiday rental in Winthrop
Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston, holiday rental in Winthrop
Walk to subway and beach, 10 mins by T to airport and 15 mins to downtown Boston, holiday 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
More info
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sterns & foster queen size bed , holiday rental in Winthrop
sterns & foster queen size bed , holiday rental in Winthrop
sterns & foster queen size bed , holiday rental in Winthrop

sterns & foster queen size bed

Private Room
1 bedroom
1 bathroom
Sleeps 1
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Cozy Bedroom, holiday rental in Winthrop
Cozy Bedroom, holiday rental in Winthrop
Cozy Bedroom, holiday rental in Winthrop

Cozy Bedroom

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 1
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