Vacation rentals in Snake Island

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Top-rated vacation rentals in Snake Island

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Guest favorite
A well-furnished living area features a light-colored sofa adorned with patterned cushions, complemented by a blue ottoman. A large area rug in soft tones enhances the warmth of the hardwood floor. Natural light enters through multiple windows, while a decorative chandelier hangs from the ceiling.
Home in Winthrop
4.86 out of 5 average rating, 94 reviews

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

Guest favorite
The image displays a cozy dining area with a glass-topped table surrounded by four chairs. Natural light filters through the windows, highlighting oak hardwood floors and intricate wood trim. An inviting living space is visible in the background, featuring a plush seating arrangement.
Apartment in Winthrop
4.87 out of 5 average rating, 266 reviews

Grand 2BR Sleeps 6 • Boston • Airport & Beaches

Whether you’re traveling for work or vacation, solo, as a couple, with friends or family, this spacious, sun-filled 7-room apartment is the perfect home base. Comfortably sleeps up to 6 guests with 2 bedrooms, a full kitchen, living room, dining room, sunroom, 2 private porches, free off-street parking, oak hardwood floors, original gumwood trim, and on-site coin laundry. Minutes from Logan Airport, public transportation, beautiful Winthrop and North Shore beaches, and Boston’s top attractions.

Guest favorite
A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.
Guest suite in Winthrop
4.92 out of 5 average rating, 1398 reviews

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.

Top guest favorite
Condo in Winthrop
4.99 out of 5 average rating, 241 reviews

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.

Top guest favorite
Apartment in Winthrop
4.98 out of 5 average rating, 52 reviews

Ocean View Beachfront | Near Boston | Free Parking

Wake up to ocean views with the sun rising over the water from your window. On clear nights, watch the moon rise and reflect on the waves. This beachfront retreat, designed for couples, blends relaxation, romance, and adventure. Nestled in Winthrop, MA, just minutes from Boston, this private in-law oceanfront escape offers direct beach access and stunning views. Take a scenic summer ferry ride to Boston, explore local waterfront restaurants, or simply relax to the soothing sound of the waves.

Top guest favorite
The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.
Condo in Winthrop
4.98 out of 5 average rating, 120 reviews

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. An historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two condos and renovated).

Top guest favorite
Apartment in East Boston
5.0 out of 5 average rating, 26 reviews

Modern Waterfront 1 Bed 5 min walk to T & Beach

Modern 1 bed with amazing amenities & view. 5 min walk to the subway, beach or marsh with a responsive owner who lives upstairs. what's the catch? Right across the water is Logan and 2 dogs upstairs who occasionally bounce around the living room during the day Steps to minimize noise in the bedroom - Massport windows -Sound absorbing panel headboard & Additional panels - Love seat /ottoman/rugs/ soft surfaces to absorb sound -xl air purifier Customizations available with advance notice.

Top guest favorite
The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.
Cottage in Winthrop
4.98 out of 5 average rating, 504 reviews

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.

Guest favorite
A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.
Apartment in Winthrop
4.85 out of 5 average rating, 131 reviews

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to 8 guests, making it perfect for families or groups of friends. Located on the 2nd floor of a historic building, this home offers a bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area, kitchen and private deck with ocean views.

Top guest favorite
The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.
Apartment in Winthrop
4.96 out of 5 average rating, 113 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.

Top guest favorite
An open living area features warm wood floors and neutral-colored walls. A large dining table is surrounded by white chairs, with a light fixture above. A television is mounted on the wall opposite a comfortable sofa, complemented by a decorative plant and a textured area rug.
Apartment in Winthrop
4.93 out of 5 average rating, 76 reviews

Charming condo steps from beach

Escape to this renovated, 750 sq ft 1-bedroom condo in the heart of Winthrop, half a block from the ocean, and easily accessible to Boston! With cozy farmhouse decor, modern amenities, and a serene atmosphere, this charming retreat is perfect for a quiet getaway or a relaxing beach vacation. Walkable to nearby restaurants, shops, and a ferry or train ride away from downtown Boston. Ideal for couples or solo travelers looking for a calm, coastal experience.

Top guest favorite
Apartment in East Boston
5.0 out of 5 average rating, 54 reviews

3BR East Boston | Free St Parking | Near T & Logan

✨ Professionally cleaned, quiet neighborhood, free street parking 🅿️, easy access to downtown ✨ Easy transit access and room to relax. A spacious 3BR, 2.5BA home in Jeffries Point is a 5⭐ Guest Favorite in the top 5% of Boston stays. Enjoy a bright, modern layout, fast WiFi, in-unit laundry, and free street parking. Walk to the waterfront for stunning skyline views and great restaurants, with quick access to the Blue Line, Logan Airport, and downtown. 🤗

Popular amenities for Snake Island vacation rentals