Holiday rentals in Winthrop

4.87 out of 5 average rating, 68 reviews

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

Discover your dream stay in this cozy 2bed, 1bath property located in picturesque Winthrop, Ma. It's perfectly situated 5-min from Yirrell Beach offering access to relaxation & city excitement. A convenient 20min drive from the bustling heart of Boston & 15min from Logan Airport & Encore Casino. Walking distance to public transportation & easy access to city adventures. clean & beautifully furnished and has a fully stocked eat-in kitchen, and a spacious deck. Short & long term stays are welcome

4.99 out of 5 average rating, 68 reviews

Apartment in Winthrop

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

4.92 out of 5 average rating, 1,300 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.

4.91 out of 5 average rating, 286 reviews

Flat 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, 241 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.

4.99 out of 5 average rating, 186 reviews

Apartment 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.

4.89 out of 5 average rating, 76 reviews

Vibrant Winthrop Apartment - Close to Ocean!

Whether you're traveling for work or leisure, this modern Winthrop apartment is a gem! The 1-bed, 1-bath vacation rental has everything needed for a stress-free stay, like a fully equipped kitchen, WiFi, and a workspace for those clocking in remotely. Downtown Boston is easily accessible with multiple transportation options nearby, so spend time at the New England Aquarium or catch a ball game at Fenway Park. Plus, breathe in the ocean breeze and take advantage of the proximity to the beach.

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.

4.97 out of 5 average rating, 62 reviews

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

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

4.98 out of 5 average rating, 65 reviews

Private room in Lynn

Private room in a condo

Saint JeanRating, 5 stars3 weeks ago

Abdel’s place is as described. It is well decorated: simply and elegantly. Furthermore, the place is clean, obviously well taken cared of. Listed amenities works. Abdel is communicative, proactive and flexible. For example I checked in 2 hours ahead of time. Found my room cleaned, ready and comfortable. That was my mistake for checking ahead of time. He managed to accommodate me anyway. Definitely recommend Abdel’s place.

5 out of 5 average rating, 25 reviews

Solo traveler private bedroom in Winthrop

DanmarRating, 5 stars9 months ago

Beatriz and Luis were great hosts. Very accommodating and always made sure I had a great stay.

5 out of 5 average rating, 15 reviews

Private room in Lynn

Cozy Private Room

ErinRating, 5 starstoday

I loved staying here. Phuong is kind and welcoming, and her dog is a great co-host. Bed is very comfortable and room darkening shades were available. Would definitely stay here again.

Private room in East Boston

4.97 out of 5 average rating, 38 reviews

Free parking room 3

AlexandraRating, 5 stars4 days ago

This was my second stay! Will continue to be my Boston stay next time I visit. So close to Blue Lime- safe neighborhood- walkable. Free parking! Spotless and comfortable!!

Superhost

4.96 out of 5 average rating, 69 reviews

Winthrop By The Sea

PoojaRating, 5 stars3 weeks ago

Howard was an amazing host! The place itself was so cute and pretty, and there was enough room for the three of us to sleep and hang out comfortably. Howard was super friendly and the kindest host we've had so far. We had lots of engaging conversations with him and felt really close by the end of the trip. The place itself is a short Uber ride to the metro stop, from which getting into Boston is super easy. It's also next to a really great restaurant and the beach. We'll definitely be looking to stay with Howard again when we come back!

4.58 out of 5 average rating, 24 reviews

Winthrop by the Sea

Myoung WoonRating, 5 stars2 weeks ago

Great place if you are staying for 1 or 2 nights! It is a bit far from Boston, but blue line station is nearby

4.97 out of 5 average rating, 72 reviews

2 - Jeremiah Suite & Private Deck (180 sq ft)

TaylorRating, 5 stars7 months ago

We loved staying here! We felt so welcomed and comfortable. It was easy to find and parking was great! It was a beautiful place!