Holiday rentals in Boston

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!

Theatre | Arcade | Pool w. Free 3 Car Parking

Experience The Chelsea Retreat, your private escape with free parking for up to 3 cars and an average 15 minute drive to Boston’s top attractions! Enjoy a cinematic night with a 150” 4K theatre and immersive surround sound, challenge friends in the arcade with foosball, pinball, and classic arcade games, or unwind beneath the gazebo before floating the day away in the pool. Shoot hoops, fire up the BBQ, or retreat to a quiet, dedicated workspace. Luxury, fun, and convenience all in one place.

Penthouse 2 Beds /2 Baths luxury in South Boston

Kick back and relax in this calm, stylish space. You won’t even feel like you are in the center of the city . Everything you need is within a walking distance , bars , coffee shops and many restaurants to choose from. Top floor unit, private balcony with 2 full bedrooms & 2 full bathrooms on opposite sides of the house makes traveling in groups much more comfortable. Brand new build 2023 , this is a hotel like stay professionally managed but with the comfort of a home away from home

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

A brand new spacious 3rd floor apartment over 1,000 sq ft centrally locate, near 2 subway stations/bus line, 4 grocery stores within 10 mins walk. The apt has a big kitchen, roof top deck and a huge yard. All brand new furnitures from Crate & Barrel, Pottery Barn and West Elm. Bed sheet sets from Crate & Barrel. NO Cleaning fee. We offer a great atmosphere, high quality amenities and cleanliness are utmost importance. Please read the reviews from prior guests.

Hipster Basecamp | Fireplace • Views • Parking

Welcome to Hipster Basecamp, a curated space where mid-century design meets modern comfort. Enjoy bold touches like a double-sided fireplace, Smeg appliances, and a ceiling-mounted rain shower. Brew espresso or mix cocktails with everything at your fingertips, then head to the deck to unwind and take in the peaceful view. Admire original artwork throughout — and if a piece speaks to you, it's available for purchase. (*note: record player is currently out of order)

Cozy studio in Bay Village near Public Garden

This newly renovated private studio is ready to welcome you! This unit has 1 queen bed and 1 sleeper sofa, a desk, a kitchenette, a full bathroom, and a washer/dryer. It is the lower level of a historic 1800s Bostonian house, recently renovated. It has its own separate entrance. Great location! Conveniently located in Bay Village next to the Boston Public Garden, the studio is close to Downtown, Theater district, Chinatown, Beacon Hill, Back Bay, and South End!

Private luxury penthouse in Boston downtown.

Experience luxury living in the heart of Downtown Boston. This stunning penthouse offers breathtaking city views, elegant modern furnishings, and a spacious layout designed for comfort and style. Enjoy floor-to-ceiling windows, premium amenities, and easy access to Boston’s top restaurants, shopping, nightlife, and historic attractions. Whether you’re visiting for business or leisure, this exclusive retreat delivers a five-star experience above the city skyline.

South End Historic Rowhouse | Reunions + World Cup

In the heart of Boston’s South End is this newly finished, design-forward 3 bedroom, 2.5 bath historic brick rowhouse. Stay in a legacy neighborhood with classic architecture, tree lined streets, and true character. This home is high-end with thoughtful finishes and furnishings. Laundry, fireplace, and private outdoor space. Surrounded by green parks, cafes and restaurants, and one block from Boston’s only Michelin-star. Accessible to the best of the city.

Your own cottage in the city

Whether you need to relax, be productive, or have a safe home base for your adventures, the Sowden cottage has you covered. Nestled near the heart of Roslindale, the cottage is a short walk to shopping and dining and is near easy transportation to every part of Boston. It's the perfect place to call home while you work, visit family, or experience the city we love. Whatever brings you to Boston, we look forward to welcoming you at the cottage!

Renovated 1-Bed w/ private deck

Newly-renovated, modern apartment located directly above Remnant Brewing Satellite, in the vibrant and culturally diverse neighborhood of Wellington-Harrington. The location is perfect for someone who wants quick access to: Inman Square, East Cambridge, Harvard Square, Kendall Square, Union Square, Central Square, Davis Square, Charlestown, and Downtown Boston. Easy access to Fenway, TD Bank North, theaters, venues, and the hospitals.

Cambridge Cottage Retreat Near Harvard

Escape to a charming Cambridge cottage just a 15 minute walk (4 min drive) to Harvard Square. Enjoy the best of both worlds - steps from vibrant shops, cafes, and restaurants, yet tucked away as a peaceful retreat. Dine in a cozy nook overlooking a sun dappled garden oasis. This one-bedroom features a queen bed, plus a full pullout sofa in the open living area - perfect for someone travelling alone, couples or small families.

The Weiss : Modern Gallery • Historic Property!

Stay inside a historic restored monastery in Brighton. This spacious studio blends preserved historic architecture with modern comfort and features an expandable room divider for a one-bedroom feel. Just a 5-minute walk to the T with easy access to Boston College, Harvard, hospitals, and downtown Boston. Amenities Include: → Blazing-fast WiFi → 65” Smart TV → Fully stocked kitchen → Washer & dryer → Comfortable queen bed