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Holiday homes in Winthrop You’ll Love

Top-Rated Winthrop Holiday homes for Every Budget and Style!

Looking for a holiday home in Winthrop (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Winthrop.

We found 17 Holiday-homes in Winthrop and the surrounding area (within 30 miles)

Revere Luxury House, Private Beach in Revere, USA

Revere Luxury House, Private Beach

Villa in Revere near Winthrop, Massachusetts , 115 Lynnway
Providing a garden, Revere Luxury House, Private Beach offers accommodations in Revere.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $309.15 Show details »

Upscale Penthouse w Gym & Parking near MGH & TUFTS in Boston, USA

Upscale Penthouse w Gym & Parking near M...

Holiday home in Boston near Winthrop, Massachusetts , 99 Kneeland Street
Just a 12-minute walk from Boston Tea Party Ship & Museum and 0.8 miles from Back Bay, Upscale Penthouse w Gym & Parking near MGH & TUFTS features acc...
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $68.00 Show details »

Waterfront Retreat with Deck about 7 Mi to Boston! in Winthrop, USA

Waterfront Retreat with Deck about 7 Mi...

Holiday home in Winthrop, Massachusetts
Waterfront Retreat with Deck about 7 Mi to Boston! offers accommodations in Winthrop, 1.1 miles from Winthrop Beach and 7.3 miles from Freedom Trail.
  • Parking

Fabulous 2 Reviews 9.0

from $55.00 Show details »

Beacon Hill: The Aldrich House in Boston, USA

Beacon Hill: The Aldrich House

Holiday home in Boston near Winthrop, Massachusetts , 59 Mount Vernon Street
Housed in a historic building, Beacon Hill: The Aldrich House features accommodations with a garden and free Wifi in Boston, a 8-minute walk from King...
  • Pets allowed
  • Bar
  • Family rooms

Exceptional 7 Reviews 9.8

from $72.00 Show details »

Private Home Near Kendall Sq - CM-241 in Cambridge, USA

Private Home Near Kendall Sq - CM-241

Holiday home in Cambridge near Winthrop, Massachusetts , Cardinal Medeiros Avenue 241
Private Home Near Kendall Sq - CM-241 is located in Cambridge, just 1.6 miles from Peabody Museum and 1.8 miles from Harvard Square.
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 in Cambridge, USA

Luxury Apartment w King Bed Shared Pool...

Holiday home in Cambridge near Winthrop, Massachusetts , 151 North First Street
Just 1.1 miles from TD Garden and 1.2 miles from Freedom Trail, Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 features accommodations in Cam...
  • Pets allowed
  • Fitness centre
  • Swimming pool
  • Swimming Pool

no reviews

from $73.00 Show details »

3BR2Bth parking, CambridgeBoston, WD, Subway, AC in Somerville, USA

3BR2Bth parking, CambridgeBoston, WD, Su...

Holiday home in Somerville near Winthrop, Massachusetts , 30 Horace Street 2 Floor
3BR2Bth parking, CambridgeBoston, WD, Subway, AC is a recently renovated vacation home in Somerville, near Inman Square.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 14 Reviews 9.6

from $500.77 Show details »

3BR2Bth parking Cambridge Boston in Somerville, USA

3BR2Bth parking Cambridge Boston

Holiday home in Somerville near Winthrop, Massachusetts , 30 Horace Street 1 Floor
3BR2Bth parking Cambridge Boston is located in Somerville, just a 14-minute walk from Inman Square and 1.2 miles from Central Square Theatre.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 10 Reviews 9.8

from $254.44 Show details »

Forever Green Manor - 6 bedroom - Stunning Ocean Views in Winthrop, USA

Forever Green Manor - 6 bedroom - Stunni...

Holiday home in Winthrop, Massachusetts , 90 Highland Avenue
Forever Green Manor - 6 bedroom - Stunning Ocean Views offers accommodations in Winthrop, a 8-minute walk from Short Beach and 1.5 miles from Donovan ...
  • Parking
  • Family rooms

Exceptional 4 Reviews 9.7

from $1.726.66 Show details »

3 BR with parking near Downtown Boston in Somerville, USA

3 BR with parking near Downtown Boston

Holiday home in Somerville near Winthrop, Massachusetts , 15 Maine Terrace 2 Floor
3 BR with parking near Downtown Boston is a recently renovated vacation home in Somerville, near Cambridge College.
  • Parking
  • Pets allowed
  • Family rooms

Superb 9 Reviews 9.3

from $254.44 Show details »

Pet-Friendly Revere Getaway, Steps from the T! in Revere, USA

Pet-Friendly Revere Getaway, Steps from...

Holiday home in Revere near Winthrop, Massachusetts
Pet-Friendly Revere Getaway, Steps from the T! is located in Revere, just 5.5 miles from Freedom Trail and 5.6 miles from Boston North Station.
  • Parking
  • Pets allowed

Very good 1 Reviews 8.0

from $241.64 Show details »

Revere Home Getaway in Revere, USA

Revere Home Getaway

Holiday home in Revere near Winthrop, Massachusetts , 20 Curtis Road
Revere Home Getaway is located in Revere, just a 8-minute walk from Revere Beach and 1.3 miles from Short Beach.
  • Parking
  • Pets allowed

no reviews

from $63.00 Show details »

CityScape in Chelsea, USA

CityScape

Holiday home in Chelsea near Winthrop, Massachusetts , 11 Lash St
CityScape is located in Chelsea, just 3.9 miles from Boston North Station and 3.9 miles from TD Garden.
  • Parking

no reviews

from $375.96 Show details »

Mystic River Escape Home Gym Office Near Encore in Medford, USA

Mystic River Escape Home Gym Office Near...

Holiday home in Medford near Winthrop, Massachusetts
Mystic River Escape Home Gym Office Near Encore is located in Medford, just 2.2 miles from Cambridge College and 3 miles from Inman Square.
  • Parking

no reviews

from $94.00 Show details »

In-between the Coast and the City in Everett, USA

In-between the Coast and the City

Holiday home in Everett near Winthrop, Massachusetts
In-between the Coast and the City is located in Everett, just 2.6 miles from Cambridge College and 3.9 miles from Freedom Trail.
  • Parking

Very good 4 Reviews 8.0

from $336.74 Show details »

Charming Boston Area Home Less Than 1 Mi to Revere Beach! in Revere, USA

Charming Boston Area Home Less Than 1 Mi...

Holiday home in Revere near Winthrop, Massachusetts
Charming Boston Area Home Less Than 1 Mi to Revere Beach! is located in Revere, just 7 miles from Kings Chapel and Burying Ground and 7.1 miles from F...
  • Parking
  • Spa and wellness centre

Fabulous 1 Reviews 9.0

from $81.00 Show details »

Seaside Serenity Boston Pet Frndly Htd Pool in Revere, USA

Seaside Serenity Boston Pet Frndly Htd P...

Holiday home in Revere near Winthrop, Massachusetts , 90 Whitin Avenue
Seaside Serenity Boston Pet Frndly Htd Pool is located in Revere, just a few steps from Revere Beach and 8.2 miles from Peabody Essex Museum.
  • Pets allowed

Exceptional 2 Reviews 10.0

from $78.00 Show details »

Number of Holiday homes in Winthrop 17
Number of guest ratings 392
Average price per night $342.00
Lowest price per night $53,00
Highest price per night $3.129,32

Top 10 Cheapest Holiday-homes in Winthrop

Discover the Cheapest Holiday-homes in Winthrop – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Winthrop

Check out the Most Booked Holiday-homes in Winthrop – Based on Guest Popularity.

Holiday homes in Winthrop (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Winthrop can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Winthrop for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Winthrop should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com