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Winthrop Vacation Rentals

Find 409 available home rentals from 9 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Winthrop

Find your perfect vacation rental in Winthrop from just $66 per night!

Villa Winthrop
-26%
Jun 23 - Jun 30
Free cancellation
Villa ∙ 10 guests ∙ 1 bedroom

242 m² Villa

Winthrop, Suffolk County, Massachusetts, United States
$2,020$2,028
per night
$2,020$2,028
per night
View deal
Apartment Winthrop
-55%
Mar 7 - Mar 14
Free cancellation
Apartment ∙ 6 guests ∙ 3 bedrooms

90 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$628$589
per night
$628$589
per night
View deal
Bed and breakfast Winthrop
Apr 12 - Apr 19
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chateau sur Mer Bed & Breakfast

Winthrop, Suffolk County, Massachusetts, United States
$255
per night
$255
per night
View deal
Bed and breakfast Winthrop
-60%
Feb 22 - Mar 1
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

HomeStay Near Downtown Boston - Andrew Station Area

Winthrop, Suffolk County, Massachusetts, United States
$423$163
per night
$423$163
per night
View deal
House Winthrop
-61%
Jan 17 - Jan 24
Free cancellation
House ∙ 4 guests ∙ 2 bedrooms

102 m² House

Winthrop, Suffolk County, Massachusetts, United States
$705$272
per night
Outstanding(87 ratings)
$705$272
per night
View deal
Apartment Winthrop
-51%
Apr 24 - May 1
Free cancellation
Apartment ∙ 6 guests ∙ 3 bedrooms

83 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$851$439
per night
$851$439
per night
View deal
Private room Winthrop
Feb 8 - Feb 15
Private room ∙ 2 guests ∙ 1 bedroom

Private room

Winthrop, Suffolk County, Massachusetts, United States
$105
per night
Outstanding(76 ratings)
$105
per night
View deal
Apartment Winthrop
-38%
Feb 15 - Feb 22
Apartment ∙ 3 guests ∙ 2 bedrooms

83 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$575$355
per night
$575$355
per night
View deal
Apartment Winthrop
-38%
Feb 19 - Feb 26
Apartment ∙ 2 guests ∙ 1 bedroom

18 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$318$190
per night
Outstanding(1 rating)
$318$190
per night
View deal
Apartment Winthrop
-51%
Feb 12 - Feb 19
Apartment ∙ 5 guests ∙ 2 bedrooms

77 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$553$363
per night
Good
$553$363
per night
View deal
Private room Winthrop
Sept 6 - Sept 13
Private room ∙ 2 guests ∙ 1 bedroom

Private room

Winthrop, Suffolk County, Massachusetts, United States
$105
per night
Outstanding(76 ratings)
$105
per night
View deal
Apartment Winthrop
-39%
Feb 15 - Feb 22
Apartment ∙ 6 guests ∙ 3 bedrooms

88 m² Apartment

Winthrop, Suffolk County, Massachusetts, United States
$675$413
per night
Very good(1 rating)
$675$413
per night
View deal
Private room Winthrop
Mar 1 - Mar 8
Private room ∙ 2 guests ∙ 1 bedroom

Private room

Winthrop, Suffolk County, Massachusetts, United States
$105
per night
Outstanding(76 ratings)
$105
per night
View deal
Private room Winthrop
Mar 1 - Mar 8
Private room ∙ 2 guests ∙ 1 bedroom

Private room

Winthrop, Suffolk County, Massachusetts, United States
$105
per night
Outstanding(76 ratings)
$105
per night
View deal
Private room Winthrop
Feb 8 - Feb 15
Private room ∙ 2 guests ∙ 1 bedroom

Private room

Winthrop, Suffolk County, Massachusetts, United States
$125
per night
$125
per night
View deal

Vacation Houses with pools

Apartment  Winthrop
Jul 6 - Jul 13
$409 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.3
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pool
View deal
Apartment  Winthrop
Feb 19 - Feb 26
-38%
$1,223
$1,225 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Winthrop, Suffolk County, Massachusetts, United States
Pool
View deal
Apartment  Winthrop
Jul 12 - Jul 19
$1,139 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
Pool
View deal
See all offers

Best Vacation Home Deals in Winthrop

Save up to 44%

Apartment Winthrop
Mar 15 - Mar 22
-44%
$345
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
View deal
Apartment Winthrop
Feb 14 - Feb 21
-29%
$244
$185 per night
Apartment ∙ 4 guests ∙ 1 bedroom
3.9
Good
Winthrop, Suffolk County, Massachusetts, United States
View deal
House Winthrop
Jul 11 - Jul 18
-22%
$705
$617 per night
House ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(87 ratings)
Winthrop, Suffolk County, Massachusetts, United States
View deal

Search through the 409 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 20%.

Budget-friendly Rentals in Winthrop

Find Fantastic yet Inexpensive Rentals

House Winthrop
Jul 6 - Jul 13
$575 per night
House ∙ 2 guests ∙ 1 bedroom
Winthrop, Suffolk County, Massachusetts, United States
Free cancellation
View deal
Apartment Winthrop
Jul 1 - Jul 8
$557 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
4.2
Very good
Winthrop, Suffolk County, Massachusetts, United States
View deal
Resort Winthrop
Oct 3 - Oct 10
$792 per night
Resort ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(4 ratings)
Winthrop, Suffolk County, Massachusetts, United States
View deal

Top-Rated Offers and Accommodations in Winthrop

Book Vacation Rentals with the Highest User Rating

Condo Winthrop
Dec 14 - Dec 21
-54%
$416
$240 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding(74 ratings)
Winthrop, Suffolk County, Massachusetts, United States
View deal
House Winthrop
Nov 30 - Dec 7
-39%
$946
$481 per night
House ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding(8 ratings)
Winthrop, Suffolk County, Massachusetts, United States
View deal
Resort Winthrop
Sept 26 - Oct 3
$841 per night
Resort ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(4 ratings)
Winthrop, Suffolk County, Massachusetts, United States
View deal

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Popular Rental Amenities in Winthrop

  • Pool (208)
  • WiFi (402)
  • Pet-friendly (176)
  • Kitchen (183)
  • Air conditioning (386)
  • Parking (14)
  • Washing machine (220)
  • TV (348)
  • Dishwasher (93)
  • Balcony/patio (81)
  • Microwave (216)
  • Grill (35)

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 more than two-thirds of the rentals in this destination.

Information about vacation rentals in Winthrop

🏡 Vacation rentals available 409 rentals
💳 Possible discounts up to 20%
🌙 Nightly prices starting at $66
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 170 homes
🏊 Vacation rentals with pools 208 homes
9,791 reviews
Winthrop vacation rentals have an average rating of 4.3/5 on 9,791 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Winthrop?

We found 409 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 170 pet-friendly vacation rentals in Winthrop, with an average nightly price of $439.

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.

Top vacation destinations in Winthrop

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