House vacation rentals in Winthrop

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Winthrop house rentals

House rentals with a pool

Guest favorite
Home in North Andover
4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

JeremyRating, 5 stars5 months ago
We had an absolutely wonderful experience staying at this Airbnb! The home was impeccably clean, cozy, and well-stocked with everything we could possibly need. The host's attention to detail was evident in every corner, from the kids' toys to the thoughtful touches like snacks, coffee, and local guidebooks. The location was perfect—peaceful and quiet but still close to shops and restaurants. I especially loved relaxing in front of the fire and enjoying the serene surroundings. The host was incredibly responsive and went above and beyond to ensure our stay was seamless, offering great tips about the area and checking in (without being intrusive). I highly recommend this spot to anyone visiting North Andover or the greater Boston area.
Top guest favorite
Home in Newton
5 out of 5 average rating, 14 reviews

Villa with private Pool in Boston's Elite Enclave

LucyRating, 5 stars5 days ago
Serge was helpful with marathon weekend details and was very responsive. House is as described, quite spacious and easily sleeps 8 adults. The game room includes billiards, darts, a massage chair, and 3 comfortable theater chairs. The kitchen is fully equipped with everything needed to prepare large family meals. It’s a 30 minute walk to the Newton Center green line train stop, which is recommended for transportation to and from downtown Boston. The price was a little high, but everything in the area was increased for marathon weekend. Would recommend.
Top guest favorite
Home in Lakeside Marblehead
5 out of 5 average rating, 13 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

ChristopherRating, 5 stars5 days ago
Everything was as listed and very responsive and great host. The property was in a very nice and in a great town. We enjoyed our time there.
Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars6 days ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Superhost
Home in Rockport
5 out of 5 average rating, 4 reviews

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

ChrisRating, 5 stars6 months ago
Great space. Loved that it was dog friendly. My older lab appreciated the amount of space! Kids enjoyed themselves and the neighborhood was quiet and the few people we ran into were very friendly.
Guest favorite
Home in Arlington
4.93 out of 5 average rating, 29 reviews

Beautiful Spacious 4BRM House!

SusanRating, 5 stars4 days ago
Maxine anticipated every possible need and so much more available. She went beyond any host I have ever stayed with and I travel quite often. I highly recommend Maxine's place
Top guest favorite
Home in Norwood
4.97 out of 5 average rating, 36 reviews

the house of id; vintage shop, accessible space

NatalieRating, 5 stars2 weeks ago
This has to be the neatest little place on Airbnb in the Boston area, and that's something to be said. Paige and Dara described the place and the experience perfectly, were a dream to communicate with, and were overall humorous hosts. Their in-house shop was very entertaining for us. We will absolutely be staying here again in the future.
Guest favorite
Home in Hull
4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

BriannaRating, 5 stars10 months ago
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Weekly house rentals

Guest favorite
Home in Salisbury
4.88 out of 5 average rating, 210 reviews

Spacious waterfront free parking &Wi-fi

AnthonyRating, 5 stars1 day ago
Had a wonderful stay here, perfect location and was able to enjoy the sounds of the ocean the entire time. Would definitely recommend staying here and I’d look forward to being here again in the future. Thank you so much!
Guest favorite
Home in South Weymouth
4.93 out of 5 average rating, 117 reviews

Entire House Near South Shore Hospital/Whole Foods

ChloeRating, 5 stars4 weeks ago
My groups stayed at Trang’s home for 2 night and our stay was perfect. The home was exactly as pictured in the listing and was very clean and spacious. Check-in instructions were straight forward and easy to understand. Would definitely stay again in the future if we ever find ourselves in the area.
Top guest favorite
Home in Newburyport
4.99 out of 5 average rating, 129 reviews

“Salty Girl” Plum Island, MA

AshleyRating, 5 stars3 days ago
Another amazing stay at Salty Girl! Erin’s home is spotless and calm and inviting. There were so many small touches to make a family’s stay easy like a toy drawer, step stool in the bathroom, and stuffed animals for the kids in the bunk room! Truly so thoughtful. The location couldn’t be better with an easy walk to the bay and beach. Really peaceful surroundings. Thank you! We can’t wait to return!!!
Top guest favorite
Home in Tewksbury
4.98 out of 5 average rating, 54 reviews

Tewksbury, MA --5 night minimum stay--4 beds, 2.5 baths, quiet street, 5 min drive to shops

MaureenRating, 5 stars4 months ago
Lauren’s house was the perfect place to stay for Christmas. It had everything we could possibly need and the garage was so convenient. I appreciated the night lights throughout the house. I felt very much at home and would highly recommend staying at Lauren’s!
Guest favorite
Home in Lexington
4.92 out of 5 average rating, 119 reviews

Mid-Century Modern in Historic Lexington

MichaelRating, 5 stars3 weeks ago
Great place for our coaches to meet up and sleep after a full day of coaching in Boston area. Very comfortable space. Highly recommend this home.
Top guest favorite
Home in Wrentham
4.88 out of 5 average rating, 105 reviews

Backyard Oasis with Hot Tub

AndresRating, 5 stars2 months ago
A wonderful place that felt even larger than in the pictures, surrounded by beautiful scenery, offering complete privacy, and the perfect touch of a delicious hot tub experience under a snowy night.
Superhost
Home in Woburn
4.88 out of 5 average rating, 135 reviews

Large 4Bed 2Bath Clean Alternative to Hotel Living

AshleeRating, 5 stars1 week ago
The apartment was as listed, and very clean, with all the amenities we needed to stay there. It was centrally located to all the areas we went to. The directions to get in were very clear. Dev was very responsive when I contacted him and it was overall a great stay.
Guest favorite
Home in Framingham
4.97 out of 5 average rating, 145 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

NathanRating, 5 stars5 months ago
Amazing price and amazing place to spend Halloween! Great places to eat and adventure around! The house was peaceful but had very friendly atmosphere with the neighbors. If I could have Andrea be the host for every air bnb I would be greatful knowing I have someone that's reliable and great with communication. She will treat you right and has great recommendations!

Private house rentals

Top guest favorite
Home in Marshfield
4.93 out of 5 average rating, 71 reviews

Winterfell - Beautiful Beachhouse (Private Beach!)

PegRating, 5 stars4 months ago
Tommy was great. He was easy to contact and communicated wonderfully. The house was set up for a guest with everything you needed for a comfortable stay. The furniture and beds were so comfortable as well as the welcoming feel. Plenty of spacious rooms. Even spaces you could have alone time. When they described the house on the ocean, it really is. This was by far the best Airbnb we’ve stayed at. Hope to rent it again next year. I can’t say enough on how comfortable the house is. This is the first house we’ve recommend for other people to stay at. Peg
Guest favorite
Home in Reading
4.95 out of 5 average rating, 61 reviews

Charming Home in Reading with a Large Yard

T.J.Rating, 5 stars1 week ago
We thoroughly enjoyed our stay. The location was wonderful and the hosts were extremely easy to work with
Guest favorite
Home in Salem
4.95 out of 5 average rating, 149 reviews

Quaint Little New Hampshire Lake House Getaway!

NaserRating, 5 stars3 weeks ago
James was an excellent host for my family and me. We thoroughly enjoyed the place and its beautiful surroundings.
Guest favorite
Home in Southborough
4.88 out of 5 average rating, 164 reviews

Luxury Living at its Best in X-Large 8 Beds Estate

KateRating, 5 stars2 months ago
We had a wonderful 2 day work retreat!! Plenty of space for work colleagues to spread out but many options for us to be together! It was wonderful!
Top guest favorite
Home in Norwood
4.95 out of 5 average rating, 39 reviews

The Cozy Colonial - 4 BDRM house with parking

CalebRating, 5 stars2 weeks ago
What an absolutely lovely home that our family was thrilled to stay at! Very clean, quiet, and comfortable. Close to everything!! Certainly a 5 star stay!
Top guest favorite
Home in Swampscott
5 out of 5 average rating, 22 reviews

The House by the Sea

AngelicaRating, 5 stars5 months ago
This was the PERFECT place for my family’s girls trip to Salem. It was only a 12 minute drive into town. The house is breathtaking!!! The pictures do not do it any justice. Everything is spotless and very welcoming. The private beach is a 3 minute walk up the road. The neighborhood is very peaceful and the neighbors were also very friendly. Tracy was an amazing host!!! 10/10 recommendation.
Guest favorite
Home in Marshfield
5 out of 5 average rating, 37 reviews

Lovely Family House Steps Away from Sandy Beach

ChevonRating, 5 stars4 months ago
Loved my stay at this beautiful home. Very clean, and felt like home. All my friends slept well and were comfortable everywhere we gathered in the home. Dominique was wonderful and responsive. I would certainly rent this again in the future.
Superhost
Home in Marshfield
4.86 out of 5 average rating, 14 reviews

"The Fieldstone Beach House"

JenniferRating, 5 stars7 months ago
Nice place with everything we needed in it. Andreas was super great. We went in a fishing charter and he let us borrow a cooler for our trip. The showers were amazing. The outside sitting area with a fire pit was one of the greatest features. We are a cooking family and although there were two cooking areas to stay together and cook it was a tight fit. What we got for the price was a really good deal.

Quick stats about house rentals in Winthrop

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore

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