Vacation rentals 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).

Cody’s Place | Boston Area Pool, Beach & Parking

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

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.

Truly Oceanfront! Spacious Family Petfriendly Home

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.

Vacation by the Sea

We welcome you to our comfortable getaway one block from the sea ! Beautiful and newly renovated. Located in a family neighborhood with houses close together so very important that our guests are respectful, in terms of noise and disturbances . Absolutely no parties are allowed. As a tight knit neighborhood, we will be alerted if house rules are not obeyed . We love treating guests with special touches upon request. Additional amenities, for a fee, can enhance the enjoyment of your stay.

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.

Cozy Basement Apartment-Stoneham

This is a private in-law apartment in the basement of the home. Full Kitchen/living room combination, full bath and 1 bedroom with private entrance. Close to Routes 93 and 128 and 95. 15-45 minute drive to Boston depending on the traffic and time of day. Convenient to grocery stores and shopping plaza, casino. We live in the main house above the apartment. There is potential for a little overhead noise. Please read the whole listing and house rules. Must be 21 to request this listing!

Near Boston / Everett historic two-bedroom

Cozy 2-bedroom apartment in charming historic 1920's home with original bathroom and original woodwork throughout, updated with modern amenities. Enjoy an amazing night's sleep on new luxury mattresses topped with crisp hotel-style linens, dreamy pillows, and cozy comforters. Cook dinner in the fully-stocked kitchen. A short Uber or subway ride into Boston. Close to Encore Casino, Assembly Row; and centrally located for day trips to Salem, the ocean, or the lakes and mountains of NH.

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with 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.

Shoreview Studio Lounge

This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.