Holiday houses in Winthrop

4.92 out of 5 average rating, 1,303 reviews

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.

4.92 out of 5 average rating, 321 reviews

Guest suite in Revere

Private Studio 10 min from airport

Private guest suite is centrally-located for easy access to the city. Professionally cleaned. You’ll have a private entrance to come and go as you’d like with a code keypad door. Our newly renovated BASEMENT 500 sq ft is perfect for a guests to escape for a few days. Private bathroom and kitchenette, 10 min away from airport. Bus and train station walking distance. 15 min walk to Revere Beach We are in close proximity to Downtown Boston as well as Salem and other areas. Free wifi Street parking

4.91 out of 5 average rating, 288 reviews

Apartment in Beachmont

Boston 3 Room Apt 5 Min Walk to Train & Beach

Listing description Sunny 3 room apartment with private entrance. Just 1 block from the ocean and short walk to Revere Beach. The MBTA Blue Line is a short 10 minute walk, be at Logan Airport or Downtown Boston in minutes. The apartment has a full kitchen, spacious master bedroom with king size bed and TV. The living room has a TV, sofa, comfortable twin size day bed with a privacy door between B.R. and L.R. Visit historic Salem via public transportation. Laundry on site. Free Driveway Parking.

4.96 out of 5 average rating, 244 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

4.94 out of 5 average rating, 130 reviews

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

4.99 out of 5 average rating, 187 reviews

Condo in Winthrop

Truly Ocean-Front!: Spacious Family Home + Pets

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. 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.

4.99 out of 5 average rating, 123 reviews

Apartment in Beachmont

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

4.98 out of 5 average rating, 466 reviews

Cottage in Winthrop

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, 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.

Superhost

4.74 out of 5 average rating, 175 reviews

Heavenly Hideaway Boston Airport Beach Park Free

Private spacious 1 bedroom 1 bath attic apartment with new rug/paint/ac. Nice little skyline view of Boston in a beautiful safe quiet residential neighborhood. Great place to rest your head or use as a base to Boston The Encore Casino Salem & beyond! Bedroom comfy mattress/sheets 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas sofa bed 55” Smart TV sitting chair table 2 chairs/lamps Kitchenette fridge microwave Keurig toaster oven dishes silverware glass

4.95 out of 5 average rating, 933 reviews

Guest suite in Winthrop

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

4.94 out of 5 average rating, 152 reviews

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

Superhost

Guest suite in Winthrop

4.86 out of 5 average rating, 118 reviews

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

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Other great holiday rentals in Winthrop

5 out of 5 average rating, 12 reviews

Sunny 2br appt close to Boston/Airport/Beaches.

LoriRating, 5 stars1 month ago

My family and I loved our stay at Olga’s gorgeous house! We were there for five weeks with our two young sons, and it exceeded all our expectations. Not only is the space large and light-drenched, it’s nicely decorated and equipped with everything you could need. And the neighborhood is wonderful—a quick walk to the water with friendly neighbors. Olga was incredibly kind and helpful—the perfect host. If you’re looking for a large, comfortable space near the beach and not far from Boston, I highly recommend you check out her place!

Superhost

Home in Winthrop

4.84 out of 5 average rating, 75 reviews

Sunny 3 bedroom on beach

KenRating, 5 stars4 weeks ago

I had a very nice time. The place was perfect. Couldn't have asked for anymore.

4.89 out of 5 average rating, 76 reviews

Vibrant Winthrop Apartment - Close to Ocean!

EdmondRating, 5 stars3 weeks ago

We had a great stay! The place was cozy and comfortable, located conveniently close to both the airport and the city center. The backyard was a lovely bonus, perfect for relaxing. The host was very kind and responsive whenever we had questions. Would definitely recommend it to others!

4.97 out of 5 average rating, 63 reviews

Pleasant Place 2

SiennaRating, 5 stars2 weeks ago

We had the best weekend. This Airbnb is a great size for 2 people. Clean, cozy and you have everything you need. Close to the city but you’re right by the ocean. Great restaurants nearby. We stayed to celebrate our engagement and attend a concert at Suffolks downs. We would definitely visit again. Easy to find and easy to get into. Nice and quiet neighborhood.

Home in East Boston

4.76 out of 5 average rating, 200 reviews

Renovated Cozy City Getaway

ЗияRating, 5 stars2 weeks ago

We did like the place and enjoyed it. Place to work from home and available parking space on the street made this property best for us. Traveled for Shakira's concert, unfortunately it was canceled. There is a train Rails and it is close to the airport. I wouldn't suggest to those who is noise sensitive. Overall I was satisfied with the price and quality. Thanks.

4.87 out of 5 average rating, 69 reviews

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

Kasey Kiley SlotterRating, 5 stars5 days ago

Carmen was a wonderful host! The location is perfect to walk everywhere to get a bite to eat or get needed items. Ferry not far away if you want to take it back and forth to Boston. The place was very clean, beds were extremely comfortable, and we had everything we needed.

4.85 out of 5 average rating, 20 reviews

Charming condo steps from beach

DaphaneRating, 5 stars2 weeks ago

I am so thankful for this location. Casie has everything you need or want. If you think you left something before coming, don't worry, she'll have it there. Plenty of pots and pans to cook, if you like. My husband and I stayed during the week, so it was quiet and very peaceful. The neighbors are friendly. Walking distance from the ocean and plenty of restaurants, convenient stores or the market. Very convenient place to stay. Also, the bed is so comfortable and the place is clean. Spacious living room, dinning room and kitchen. We would definitely come back. Thanks again!