Winthrop vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Winthrop

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

Guest favorite
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.
Nov 16 – 23
$179 per night
4.96 out of 5 average rating, 275 reviews
Guest favorite
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.
Jun 4 – 11
$215 per night
4.99 out of 5 average rating, 412 reviews
Guest favorite
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.
Sep 2 – 9
$272 per night
4.95 out of 5 average rating, 147 reviews

Popular amenities for Winthrop vacation 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 vacation rentals in Winthrop

Guest favorite
Barn in Nahant
Entire Beach-Town Cottage, Barn Charm, near Boston
Mar 20 – 27
$217 per night
5.0 out of 5 average rating, 104 reviews
Superhost
Bungalow in Revere Beach
Cape cod style seaside condo Boston, Airport,Train
Aug 19 – 26
$452 per night
4.82 out of 5 average rating, 123 reviews
Guest favorite
Guest suite in Everett
Basement Apartment in prime location near Boston
Dec 6 – 13
$120 per night
4.92 out of 5 average rating, 214 reviews
Superhost
Apartment in Lynn
First Floor Flat Located Between Boston, Salem
Apr 21 – 28
$102 per night
4.89 out of 5 average rating, 218 reviews
Guest favorite
Guest suite in Nahant
The Annex Oceanfront
Feb 2 – 9
$134 per night
4.98 out of 5 average rating, 339 reviews
Guest favorite
Guest suite in Peabody
Cozy West Peabody Guest Suite
Jul 4 – 11
$102 per night
4.98 out of 5 average rating, 177 reviews
Guest favorite
Guest suite in Scituate
Private Scituate Getaway - walk to harbor
Mar 27 – Apr 3
$95 per night
4.91 out of 5 average rating, 172 reviews
Guest favorite
Loft in Swampscott
Gorgeous Oceanfront Penthouse
May 20 – 27
$332 per night
5.0 out of 5 average rating, 249 reviews
Guest favorite
Guest suite in Revere
Adorable studio with pool
Dec 4 – 11
$135 per night
4.86 out of 5 average rating, 129 reviews
Superhost
Apartment in Weymouth
Lovely studio on the coast! Beach close by!
Sep 3 – 10
$111 per night
4.81 out of 5 average rating, 156 reviews
Guest favorite
Guest suite in Arlington
Modern and comfortable studio apartment
Jan 1 – 8
$93 per night
4.92 out of 5 average rating, 192 reviews
Guest favorite
Guest suite in Stoughton
Modern private studio with outdoor hot tub!
Oct 25 – Nov 1
$239 per night
4.99 out of 5 average rating, 153 reviews

Other great vacation rentals in Winthrop

Superhost
Apartment in Winthrop
Sunny 2br appt close to Boston/Airport/Beaches.
Mar 21 – 28
$140 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Winthrop
Cozy & Modern Entire Residential Home ❤️
Nov 27 – Dec 4
$270 per night
4.84 out of 5 average rating, 44 reviews
Guest favorite
Home in Winthrop
The Day-Burrill-Wadsworth-La Voix House
Oct 17 – 24
$359 per night
5.0 out of 5 average rating, 22 reviews
Guest favorite
Apartment in Winthrop
Oceanfront apartment, 15min from Boston!
Nov 21 – 28
$309 per night
4.86 out of 5 average rating, 64 reviews
Guest favorite
Home in Winthrop
Luxury 3BR/2BA Home Featured in Boston Magazine
Sep 16 – 23
$533 per night
5.0 out of 5 average rating, 24 reviews
Guest favorite
Apartment in Revere
2 Bedroom Apartment with Ocean Views
Feb 7 – 14
$225 per night
4.9 out of 5 average rating, 42 reviews
Guest favorite
Vacation home in Winthrop
Sunny, spacious 3 BR on Winthrop beach
Jul 14 – 21
$488 per night
4.97 out of 5 average rating, 32 reviews
Guest favorite
Home in Revere
Seaside Serenity Boston -Pet Frndly+Htd Pool
May 2 – 9
$654 per night
5.0 out of 5 average rating, 9 reviews
Guest favorite
Apartment in Revere
Spacious 3 Bedroom Apartment with King Bed
Aug 10 – 17
$200 per night
4.98 out of 5 average rating, 81 reviews
Guest favorite
Guest suite in Winchester
Warm and cozy 1st flr sweet guest suite w parking
Jan 27 – Feb 3
$88 per night
5.0 out of 5 average rating, 95 reviews
Guest favorite
Guest suite in Revere
Corner Cottage - cozy studio just north of Boston
Sep 2 – 9
$113 per night
4.95 out of 5 average rating, 92 reviews
Guest favorite
Apartment in Revere
Beautiful Cozy and lovely one bedroom apartment.
Aug 13 – 20
$156 per night
4.96 out of 5 average rating, 48 reviews

Quick stats about vacation 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

$40 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 160 vacation rentals in Cottage Park, over 160 vacation rentals in Beachmont, and over 2,210 vacation rentals in Orient Heights.

  • 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 80 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Winthrop vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Winthrop, available on Airbnb. Make a splash and soak up the sun in style!

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

    Experience the best of Winthrop with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Winthrop have air conditioning?

    Absolutely! We offer over 60 apartment 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 60 apartment rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Winthrop?

    Winthrop has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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