Holiday rentals in Winthrop

4.87 out of 5 average rating, 70 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, 1,303 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

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, 246 reviews

Flat in Winthrop

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, 187 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.

4.99 out of 5 average rating, 124 reviews

Flat 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!

4.9 out of 5 average rating, 77 reviews

Flat in Winthrop

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, 468 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.

4.74 out of 5 average rating, 176 reviews

Flat in Winthrop

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, 934 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.

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Other great holiday rentals in Winthrop

Private room in East Boston

4.89 out of 5 average rating, 705 reviews

15min T to Downtown, Walk to airport & subway

XimenaRating, 5 stars2 weeks ago

Totana's accommodation was perfect for our night in Boston, as the next day we had to leave early for the airport. The house was super clean, as was the bathroom, and the bed was very comfortable.

4.96 out of 5 average rating, 69 reviews

Winthrop By The Sea

PoojaRating, 5 stars1 month 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!

4.78 out of 5 average rating, 50 reviews

Private room in Revere

Saltwater Nook

IanRating, 5 stars4 weeks ago

Cemal was a wonderful host. Very hospitable and clear instructions for the stay. Provided recommendations of things to do during the stay which was very kind. Would absolutely recommend to anyone staying in the area.

4.58 out of 5 average rating, 24 reviews

Winthrop by the Sea

Myoung WoonRating, 5 stars1 month 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, 73 reviews

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

AshleyRating, 5 stars2 days ago

We had a very comfortable stay here! The room was immaculate and the house was well situated. The home was well preserved and very charming. The only issue was that this place is not very accessible by transit, but there is parking available onsite.

4.89 out of 5 average rating, 91 reviews

Winthrop Home With A View

AnyiethRating, 5 stars4 weeks ago

Lana has been a welcoming host at my time in her apartment. I have never felt bored. She even went a head to suggest some of the incredible sites I should visit in Boston. I strongly recommend her place. There is a peaceful natural environment at Windhrov.

4.87 out of 5 average rating, 455 reviews

Private room in Chelsea

Private, Intimate Ocean Blue Room @ The Washburn!

ChristianRating, 5 stars4 weeks ago

Hospitable host. Made sure breakfast was available every day. The place is beautiful, well decorated. It made me want to stay longer. Donnell is great to talk to, respectful of your privacy, and available if you need anything. I had a great time.