Holiday rentals in Deer Island

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).

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand spanking new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There are two great restaurants nearby - Molinari’s and Tavolo, as well as a local coffee shop & a Dunkin just across the T Station.

Ocean View Boston Gathering Place: ChezBlue

Surround your grown-up group with spectacular ocean views in this stylish waterfront condo. This unit is the entire 3rd floor and our personal Boston home. It’s pro-cleaned, and has normal neighborhood sound-levels, including occasional air-traffic, but nothing disruptive. Adjacent to Boston by car, ferry, or public transit. Visit Salem–even Maine–or just relax. Enjoy our rocky beach or walk a few blocks to the sandy, lifeguarded area. Cafés and restaurants are walkable, and groceries deliver.

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.

The Price is Right 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

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Oceanfront Penthouse Retreat

Step into luxury at this stunning, top-floor penthouse with breathtaking panoramic views of the ocean. Perfect for a romantic getaway, family vacation, or serene retreat, this exclusive beachfront oasis combines modern elegance with coastal charm. Relax on your private terrace as you enjoy endless sea views, or take a short walk to the beach just steps from your door. Private terrace with spectacular ocean views, Direct beach access, walking distance to local dining, WIFI, smart TV, AC

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.

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.

Apartment in Revere near the airport

Enjoy the simplicity of this quiet and central accommodation. Located in a strategic area. Close to the airport, beaches, shopping malls, train station, Downtown Boston, etc. The apartment has a bedroom, large kitchen, living-dining room, full bathroom and an outside terrace overlooking the interior of the property. The living-dining room has the peculiarity of having a door with a lock so it can be used as an additional private room if required.

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

Elegant Oasis with Pool and Gym

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa