Holiday 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
Flat 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.
17–24 NovIndividual Host,
£190 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.
8–15 JunIndividual Host,
£215 per night
4.99 out of 5 average rating, 412 reviews
Guest favourite
Guest suite in Winthrop
Licensed Boston airport studio 5 stars, subway
We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.
5–12 OctIndividual Host,
£184 per night
4.92 out of 5 average rating, 1183 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
Guest suite in Nahant
Rock Steady - Panoramic Ocean Front Home
10–17 JunIndividual Host,
£313 per night
4.95 out of 5 average rating, 147 reviews
Guest favourite
Home in Quincy
Artist's Haven (2)
7–14 JunIndividual Host,
£111 per night
4.96 out of 5 average rating, 121 reviews
Guest favourite
Guest suite in Nahant
The Annex Oceanfront
14–21 JanIndividual Host,
£135 per night
4.98 out of 5 average rating, 339 reviews
Guest favourite
Flat in Revere
Quiet Neighborhood Luxury Stay
2–9 Feb
£256 per night
4.96 out of 5 average rating, 143 reviews
Guest favourite
Guest suite in Arlington
Modern and comfortable studio apartment
28 Dec – 4 Jan
£104 per night
4.92 out of 5 average rating, 192 reviews
Guest favourite
Guest suite in Scituate
Private Scituate Getaway - walk to harbor
27 Mar – 3 AprIndividual Host,
£100 per night
4.91 out of 5 average rating, 172 reviews
Guest favourite
Guest suite in Marblehead
Ocean Park Retreat
3–10 Dec
£104 per night
4.92 out of 5 average rating, 243 reviews
Guest favourite
Flat in Salem
Your home for the holidays!
25 Nov – 2 DecIndividual Host,
£126 per night
4.95 out of 5 average rating, 758 reviews
Superhost
Flat in Lynn
First Floor Flat Located Between Boston, Salem
21–28 AprProfessional Host,
£107 per night
4.89 out of 5 average rating, 218 reviews
Guest favourite
Flat in Winthrop
Sea la Vie
15–22 Jul
£337 per night
5.0 out of 5 average rating, 24 reviews
Superhost
Flat in Winthrop
Sunny 2br appt close to Boston/Airport/Beaches.
22–29 MarIndividual Host,
£176 per night
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winthrop
Newly Renovated Ocean View 2 Bdrm Apt
18–25 JanIndividual Host,
£254 per night
4.91 out of 5 average rating, 87 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

£31 before taxes and fees

Destinations to explore

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