Vacation rentals in Winthrop

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winthrop

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Winthrop
Cody's Place Boston Airport Pool/Beaches ParkFree
Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.
16–23 Nov
$396 NZD per night
4.96 out of 5 average rating, 275 reviews
Guest favourite
Cottage in Winthrop
J&K's BnB .... Private studio Airbnb with parking
Our non-smoking private Studio Bnb is located by the airport in a small safe seaside community called Point Shirley. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free wireless Wi-Fi, RokuTV, & one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.
4–11 Jun
$449 NZD per night
4.99 out of 5 average rating, 412 reviews
Guest favourite
Guest suite in Nahant
Rock Steady - Panoramic Ocean Front Home
Just north of Boston, our home is a mid century ranch we renovated in 2019. The Airbnb is a spacious separate ground floor living space surrounded by a private cove that is truly breathtaking. 1000 square feet of sunlit comfort. Enjoy the sound of the waves, stunning sunrises and a landscaped back patio that abuts our cliff. In the summer take advantage of the town beach down the street. During the winter relax in front the fireplace. Top it all off with hi-speed Wi-fi – it's a perfect getaway.
3–10 Sep
$599 NZD per night
4.95 out of 5 average rating, 147 reviews

Popular amenities for Winthrop holiday rentals

Stay near Winthrop's top sights

Boston Logan International Airport110 locals recommend
Deer Island22 locals recommend
Belle Isle Seafood27 locals recommend
Stop & Shop15 locals recommend
Angela's Cafe Orient Heights12 locals recommend
Nick's Place11 locals recommend

Other great holiday rentals in Winthrop

Guest favourite
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
16–23 Feb
$270 NZD per night
4.91 out of 5 average rating, 225 reviews
Guest favourite
Barn in Nahant
Entire Beach-Town Cottage, Barn Charm, near Boston
20–27 Mar
$479 NZD per night
5.0 out of 5 average rating, 104 reviews
Guest favourite
Guest suite in Everett
Basement Apartment in prime location near Boston
6–13 Dec
$258 NZD per night
4.92 out of 5 average rating, 214 reviews
Superhost
Apartment in Lynn
First Floor Flat Located Between Boston, Salem
21–28 Apr
$223 NZD per night
4.89 out of 5 average rating, 218 reviews
Superhost
Bungalow in Revere Beach
Cape cod style seaside condo Boston, Airport,Train
25 Oct – 1 Nov
$1,215 NZD per night
4.82 out of 5 average rating, 123 reviews
Guest favourite
Loft in Swampscott
Gorgeous Oceanfront Penthouse
27 Dec – 3 Jan
$630 NZD per night
5.0 out of 5 average rating, 249 reviews
Guest favourite
Guest suite in Nahant
The Annex Oceanfront
2–9 Feb
$280 NZD per night
4.98 out of 5 average rating, 339 reviews
Guest favourite
Apartment in Winthrop
Newly Renovated Ocean View 2 Bdrm Apt
2–9 Jan
$550 NZD per night
4.91 out of 5 average rating, 87 reviews
Superhost
Apartment in Winthrop
Sunny 2br appt close to Boston/Airport/Beaches.
21–28 Mar
$367 NZD per night
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Winthrop
Sea la Vie
21–28 Aug
$704 NZD per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Winthrop
Cozy & Modern Entire Residential Home ❤️
27 Nov – 4 Dec
$595 NZD per night
4.84 out of 5 average rating, 44 reviews
Guest favourite
Home in Winthrop
The Day-Burrill-Wadsworth-La Voix House
17–24 Oct
$797 NZD per night
5.0 out of 5 average rating, 22 reviews

Quick stats about holiday rentals in Winthrop

Total rentals

150 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

12K reviews

Nightly prices starting at

$66 NZD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Winthrop