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

Cottage in Winthrop

4.99 out of 5 average rating, 413 reviews

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 1 – 8

R4,640 ZAR per night
Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 275 reviews

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.

Jan 22 – 29

R3,887 ZAR per night
Guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 122 reviews

Beachfront Boston: Large, Cozy, Relaxed + Pets

New 2-person soaker tub with ocean-view! Gather with family & friends in this owner-hosted home. Private entrance, entire 1st floor of a multi-family home, with normal family/kid sounds. Pro-cleaned and pet-friendly, space for everyone. Scoot into adjacent Boston by car, ferry/transit, or snuggle-up for a movie on the 70” TV. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all

Dec 19 – 26

R5,608 ZAR per night

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

Superhost

Place to stay in Boston

4.79 out of 5 average rating, 187 reviews

Lovely Private Studio near Logan Airport

Apr 19 – 26

R3,264 ZAR per night
Guest favorite

Guest suite in Norwell

4.95 out of 5 average rating, 258 reviews

Private suite South Shore

Apr 30 – May 7

R2,236 ZAR per night
Superhost

Apartment in Weymouth

4.81 out of 5 average rating, 157 reviews

Lovely studio on the coast! Beach close by!

Sep 1 – 8

R2,196 ZAR per night
Guest favorite

Guest suite in Medford

4.92 out of 5 average rating, 120 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Oct 28 – Nov 4

R2,372 ZAR per night
Guest favorite

Guest suite in Nahant

4.95 out of 5 average rating, 147 reviews

Rock Steady - Panoramic Ocean Front Home

Jun 15 – 22

R6,467 ZAR per night
Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 194 reviews

Modern and comfortable studio apartment

Nov 10 – 17

R2,037 ZAR per night
Guest favorite

Apartment in Revere

4.96 out of 5 average rating, 145 reviews

Quiet Neighborhood Luxury Stay

Dec 7 – 14

R5,232 ZAR per night
Guest favorite

Guest suite in Revere

4.85 out of 5 average rating, 131 reviews

Adorable studio with pool

Sep 20 – 27

R2,956 ZAR per night
Guest favorite

Guest suite in Melrose

4.93 out of 5 average rating, 487 reviews

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

Jul 5 – 12

R1,952 ZAR per night
Guest favorite

Loft in Swampscott

5.0 out of 5 average rating, 250 reviews

Gorgeous Oceanfront Penthouse

Nov 13 – 20

R4,665 ZAR per night
Guest favorite

Guest suite in Salem

4.99 out of 5 average rating, 685 reviews

The Mason Suite of Salem

Mar 10 – 17

R2,763 ZAR per night
Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 244 reviews

Ocean Park Retreat

Mar 13 – 20

R2,515 ZAR per night

Other great vacation rentals in Winthrop

Guest favorite

Apartment in Everett

4.92 out of 5 average rating, 194 reviews

Huge 1BR w/King Bed near BOS, Salem, Water &Nature

Sep 11 – 18

R2,451 ZAR per night
Guest favorite

Barn in Nahant

5.0 out of 5 average rating, 105 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

Apr 25 – May 2

R4,832 ZAR per night
Guest favorite

Cabin in Cohasset

4.92 out of 5 average rating, 280 reviews

Lionsgate at Cohasset

Sep 2 – 9

R2,978 ZAR per night
Guest favorite

Apartment in Stoneham

4.89 out of 5 average rating, 123 reviews

Entire guest suite in Stoneham

Nov 6 – 13

R1,534 ZAR per night
Guest favorite

Apartment in Woburn

4.97 out of 5 average rating, 102 reviews

Comfy-Spacious-private 1BR conveniently located

Nov 7 – 14

R2,708 ZAR per night
Guest favorite

Apartment in Winthrop

5.0 out of 5 average rating, 24 reviews

Sea la Vie

May 29 – Jun 5

R6,668 ZAR per night
Guest favorite

Home in Winthrop

5.0 out of 5 average rating, 23 reviews

The Day-Burrill-Wadsworth-La Voix House

Dec 5 – 12

R4,044 ZAR per night
Guest favorite

Apartment in Winthrop

4.91 out of 5 average rating, 87 reviews

Newly Renovated Ocean View 2 Bdrm Apt

Mar 19 – 26

R5,691 ZAR per night
Guest favorite

Home in Winthrop

4.84 out of 5 average rating, 44 reviews

Cozy & Modern Entire Residential Home ❤️

Jul 20 – 27

R5,600 ZAR per night
Guest favorite

Apartment in Winthrop

4.86 out of 5 average rating, 64 reviews

Oceanfront apartment, 15min from Boston!

Apr 16 – 23

R6,710 ZAR per night
Guest favorite

Guest suite in Revere

4.94 out of 5 average rating, 94 reviews

Corner Cottage - cozy studio just north of Boston

Sep 10 – 17

R2,482 ZAR per night
Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 97 reviews

Warm and cozy 1st flr sweet guest suite w parking

Jan 13 – 20

R1,906 ZAR per night

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

R757 ZAR 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 2,210 vacation rentals in Orient Heights, and over 160 vacation rentals in Beachmont.

  • 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 condo rentals in Winthrop?

    Experience the best of Winthrop with our condo rentals, starting at about $80 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 condo rentals in Winthrop have wireless internet?

    Absolutely! We offer over 10 condo 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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  4. Suffolk County
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