Holiday houses in Governors Island

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Top-rated holiday rentals in Governors Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

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, 93 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 favourite

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, 1,396 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 favourite

An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.

Apartment in Boston

4.99 out of 5 average rating, 135 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

Guest favourite

Apartment in Winthrop

4.76 out of 5 average rating, 202 reviews

Private Quiet 1BR Apt • Boston • Airport & Beaches

Private 1-bedroom top-floor apartment in a quiet Winthrop neighborhood minutes from Logan Airport, Boston, beaches, restaurants, and public transportation. Features include a queen bedroom, private bath, WiFi, Smart TVs, air conditioning, kitchenette, free dedicated off-street parking, and sleeping accommodations for up to 4 guests. Note: private 3rd-FL apartment accessed by stairs. Not suitable for guests with mobility issues. Clean, comfortable home base for Boston, airport & beach trips.

Top Guest favourite

Condo in Winthrop

4.99 out of 5 average rating, 237 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 favourite

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, 503 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 favourite

Home in Boston

5 out of 5 average rating, 29 reviews

Boston Buccaneer Retreat

Modern Luxury Near Forest Hills Station – A Sophisticated Urban Retreat Experience unparalleled elegance in this brand-new, high-end residence, perfectly positioned just moments from Forest Hills Station. Designed for discerning travelers, this exquisite home blends sophisticated design, premium finishes, and state-of-the-art amenities. The Orange Line is just outside the porch . save on rental cars and enjoy a gateway to Northeastern University and all of Boston's top transit routes.

Guest favourite

An open-concept living area showcases a modern kitchen with white cabinets and stainless steel appliances. A dining table is positioned adjacent, with seating for four. Comfortable seating is provided by a light-colored sofa and stylish chairs, complemented by a textured area rug.

Condo in Boston

4.95 out of 5 average rating, 152 reviews

Modern Luxury | Free Parking, Near T | Home Cinema

Discover a stylish East Boston condo featuring modern farmhouse design and stunning Boston skyline views. Just a 5-minute walk to the Blue Line and only 11 minutes from Logan Airport, it's the perfect home base for exploring the city. This spacious 3-bedroom retreat comfortably sleeps 7 guests and includes a luxurious home theater, a fully equipped kitchen, and free parking. Enjoy the perfect blend of comfort, convenience, and a quiet neighborhood just minutes from downtown Boston.

Top Guest favourite

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, 112 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

A well-lit bedroom features a spacious bed with white bedding and decorative pillows. A bedside lamp stands next to the bed, and a window is dressed with long gray curtains. A mirror reflects the room's light, enhancing the sense of openness.

Apartment in Boston

4.87 out of 5 average rating, 204 reviews

Cozy suite in the city!

Enjoy a stylish experience at this centrally-located place in an extremely vibrant neighborhood of Boston. While staying at the AIRBNB, you will be in close proximity to the BCEC if you are in town for work. If you are in town for a pleasure, you will be very close to Downtown Boston, Fenway Park, the Seaport District, Faneuil Hall and the historic North End. You’ll be pleasantly surprised of how easy public transportation is to navigate around the city from the AIRBNB.

Top Guest favourite

A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.

Boat in Boston

4.95 out of 5 average rating, 154 reviews

2BR Spacious Yacht - Heat & AC- On Freedom Trail

The coolest way to stay in Boston: not a water view — you're ON the water. Carpe Diem II is a yacht in Charlestown Navy Yard with 2 queen staterooms, each with a private bathroom and shower, for up to 4 adults. Fall asleep to the harbor rocking you, have dinner and cocktails on the aft deck as boats cruise past, and stay comfortable with central A/C and heat. The Freedom Trail, North End, and Downtown are steps away. Hotels have views. You'll have the harbor.

Top Guest favourite

An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.

Guest suite in Winthrop

4.94 out of 5 average rating, 1,053 reviews

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.