Winthrop vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Winthrop vacation rentals

Stay near Winthrop's top sights

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
Donna's Restaurant12 locals recommend

Other great vacation rentals in Winthrop

Superhost

Place to stay in Boston

4.79 out of 5 average rating, 189 reviews

Lovely Private Studio near Logan Airport

Aug 1 – 8

€ 197 per night
Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 196 reviews

Modern and comfortable studio apartment

Dec 24 – 31

€ 126 per night
Guest favorite

Guest suite in Marblehead

4.97 out of 5 average rating, 262 reviews

Private Loft Right on Atlantic Avenue

Jul 10 – 17

€ 166 per night
Guest favorite

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Dec 8 – 15

€ 139 per night
Guest favorite

Apartment in Woburn

4.94 out of 5 average rating, 107 reviews

Comfy-Spacious-private 1BR conveniently located

Jan 7 – 14

€ 147 per night
Guest favorite

Guest suite in Melrose

4.93 out of 5 average rating, 488 reviews

Private & Cozy Suite -near Bost-Airp-Salem-Train

Aug 16 – 23

€ 120 per night
Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Apr 11 – 18

€ 156 per night
Guest favorite

Apartment in Winthrop

4.94 out of 5 average rating, 16 reviews

Vibrant Winthrop Apartment - Close to Ocean!

Dec 4 – 11

€ 134 per night

Quick stats about vacation rentals in Winthrop

  • Total rentals

    150 properties

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • 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

    € 37 before taxes and fees

Frequently Asked Questions

  • Where should I stay in Winthrop?

    Make yourself at home in Winthrop by choosing from our most frequently booked neighborhoods. We have over 2,290 vacation rentals in Orient Heights, over 150 vacation rentals in Beachmont, and over 150 vacation rentals in Cottage Park.

  • Are there pet-friendly vacation rentals in Winthrop?

    Four-legged friends are welcome in Winthrop. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Winthrop?

    Yes! Work meets play with ease at over 70 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in condo rentals in Winthrop?

    Experience the best of Winthrop with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Winthrop have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Winthrop have wireless internet?

    Absolutely! We offer over 70 apartment rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Winthrop?

    Winthrop has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Condo Rentals in Winthrop?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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