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Winthrop Vacation Rentals

Find 314 available offers from 8 partners
Winthrop
Anytime
Guests
Winthrop
Anytime
Guests

Popular Filters to find the Perfect Rental in Winthrop

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation Houses with Pools

Apartment  Winthrop
Dec 14 - Dec 21
-67%
$1,371
$455 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-Oriented Holiday Apartment with Pool

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pool
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Apartment  Winthrop
Dec 7 - Dec 14
-61%
$1,516
$589 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Family-Friendly Pleasant Apartment with Pool

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pool
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Apartment  Winthrop
Dec 7 - Dec 14
-55%
$1,814
$822 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment with Pool

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pool
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Dog-Friendly Vacation Rentals

Apartment  Winthrop
Jan 21 - Jan 28
-74%
$878
$230 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment with 3 Rooms for 8 Persons

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pet-friendly
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Apartment  Winthrop
Dec 2 - Dec 9
-72%
$869
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Beautiful Apartment | Next to the Beach | Pets Are Welcome

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pet-friendly
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Apartment  Winthrop
Dec 2 - Dec 9
-72%
$869
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment with 2 Rooms for 6 Persons

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pet-friendly
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Cabins with a sauna

Apartment  Winthrop
from $427 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Fully Equipped Pleasant Rental Apartment with Sauna & Pool | Dogs Allowed

Winthrop, Suffolk County, Massachusetts, United States
Sauna
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Apartment  Winthrop
from $305 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with Sauna & Pool

Winthrop, Suffolk County, Massachusetts, United States
Sauna
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Apartment  Winthrop
from $212 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Fully Equipped Beautiful Apartment with Pool & Sauna | Pet-Friendly

Winthrop, Suffolk County, Massachusetts, United States
Sauna
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Best Vacation Home Deals in Winthrop

Save up to 72%

Apartment Winthrop
Nov 16 - Nov 23
-29%
$512
$362 per night
Apartment ∙ 3 guests ∙ 2 bedrooms

Rental Apartment with 2 Rooms for 3 Persons

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Apartment Winthrop
Dec 2 - Dec 9
-72%
$869
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment | City View

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Apartment Winthrop
Dec 2 - Dec 9
-72%
$871
$243 per night
Apartment ∙ 8 guests ∙ 2 bedrooms

Rental Apartment with 2 Rooms for 8 Persons

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Search through the 314 vacation homes listed in Winthrop and find the perfect spot for your vacation. Using HomeToGo's search feature you can instantly search and compare the prices of each listed rental to find the best deal and save up to 72%.

Recommended Vacation Rentals in Winthrop

Find your perfect vacation rental in Winthrop: from $62 per night

Private room Winthrop
Jul 20 - Jul 27
$102 per night
Private room ∙ 2 guests ∙ 1 bedroom

Dedicated Room | Close to the Beach

4.5
Excellent (68 ratings)
Winthrop, Suffolk County, Massachusetts, United States
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Private room Winthrop
Jul 20 - Jul 27
$102 per night
Private room ∙ 2 guests ∙ 1 bedroom

Dedicated Room for 2 Persons

4.5
Excellent (68 ratings)
Winthrop, Suffolk County, Massachusetts, United States
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Private room Winthrop
Aug 10 - Aug 17
$102 per night
Private room ∙ 2 guests ∙ 1 bedroom

Private Room for 2 Persons

4.5
Excellent (68 ratings)
Winthrop, Suffolk County, Massachusetts, United States
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Private room Winthrop
Jul 20 - Jul 27
$102 per night
Private room ∙ 2 guests ∙ 1 bedroom

Dedicated Room | Close to the Beach

4.5
Excellent (68 ratings)
Winthrop, Suffolk County, Massachusetts, United States
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Apartment Winthrop
Dec 2 - Dec 9
-72%
$869
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with 2 Rooms for 6 Persons

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Apartment Winthrop
Dec 2 - Dec 9
-72%
$869
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Wonderful Holiday Apartment | Beach Nearby | Dogs Allowed

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Bed and breakfast Winthrop
Jul 27 - Aug 3
$379 per night
Bed and breakfast ∙ 6 guests ∙ 4 bedrooms

Family-Friendly Bed & Breakfast | Next to the Beach

Winthrop, Suffolk County, Massachusetts, United States
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Bed and breakfast Winthrop
Aug 28 - Sept 4
$290 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant Bed & Breakfast | Next to the Beach

3.0
Winthrop, Suffolk County, Massachusetts, United States
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Private room Winthrop
Jul 20 - Jul 27
$121 per night
Private room ∙ 2 guests ∙ 1 bedroom

Private Room with Patio & Yard

Winthrop, Suffolk County, Massachusetts, United States
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Budget-friendly Rentals in Winthrop

Find Fantastic yet Inexpensive Rentals

Apartment Winthrop
Jan 26 - Feb 2
-69%
$806
$248 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Charming Rental Apartment | Near Beacon Hill

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Apartment Winthrop
Jan 25 - Feb 1
-68%
$637
$206 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment | Near Beacon Hill

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Apartment Winthrop
Feb 1 - Feb 8
-71%
$692
$199 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Wonderful Apartment | Next to Beacon Hill

Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Top-Rated Offers and Accommodations in Winthrop

Book Vacation Rentals with the Highest User Rating

House Winthrop
Dec 7 - Dec 14
-36%
$599
$386 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home with Barbeque

5.0
Outstanding (25 ratings)
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Resort Winthrop
Nov 15 - Nov 22
$603 per night
Resort ∙ 4 guests ∙ 1 bedroom

Child-Friendly Nice Resort with Sauna | Next to Faneuil Hall

4.9
Outstanding (4 ratings)
Winthrop, Suffolk County, Massachusetts, United States
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Apartment Winthrop
Aug 17 - Aug 24
$302 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment | Pets Allowed

5.0
Outstanding
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
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Popular Rental Amenities in Winthrop

  • Pool (172)
  • WiFi (308)
  • Pet-friendly (67)
  • Kitchen (106)
  • Air conditioning (294)
  • Parking (15)
  • Washing machine (171)
  • TV (269)
  • Dishwasher (53)
  • Balcony/patio (71)
  • Microwave (186)
  • Grill (17)

Finding a vacation rental with a pool shouldn't be too hard in Winthrop. More than half of the accommodations provide one. In addition, more Apartment rental have pools than any other type of accommodation. They are a great choice if you go in a group of 9, as that is the number of people they can accommodate on average. You can also rent a vacation rental with a pool near the water, which is the case for nearly all of the rentals in this destination.

Information about vacation rentals in Winthrop

🏡 Vacation rentals available 314 rentals
💳 Possible discounts up to 72%
🌙 Nightly prices starting at $62
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 68 homes
🏊 Vacation rentals with pools 172 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Winthrop?

We found 314 vacation homes in Winthrop available for your next trip.

What are the most popular vacation home amenities in Winthrop?

Many travellers are searching for Pool, Internet, and Pets allowed when booking a vacation home in Winthrop.

Are there pet-friendly vacation rentals in Winthrop?

Yes, there are 68 pet-friendly vacation rentals in Winthrop, with an average nightly price of $458.

What's the best month to book a vacation rental in Winthrop?

When booking a vacation rental in Winthrop, remember that the rainiest months are usually December and January, with August often being the sunniest.

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