Holiday rentals with a hot tub in Dorchester

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Guest favourite

Explore Boston in style! Dream home (STR-26-3)

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, office with bed, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - desirable and safe suburb of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

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Guest favourite

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.

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Guest favourite

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

New luxury 4BR/3 bath apartment with AC & EV charger

Enjoy Halloween in Salem MA while staying in our newly renovated 4 bdrm 3 bath apartment. Full kitchen with granite countertops, wine cooler, Bosch appliances, gas stoves, dish washer, microwave oven, toaster, coffee maker, water kettle, huge fridge. Central AC. With sleeper sofa bed in living room, the place host up to 10 guests comfortably. Conveniently located in Somerville MA, we are 5 stops from north station, where a 32 minutes ride gets you to Salem. Free parking on site with EV charger.

Luxury lake retreat- pool, fire pit, trails

A spacious private retreat in nature, on a lake with trails at your door, yet minutes to major highways and easy access to Boston. Grand suite: king bed, air bed, and 2 twin beds with private half bath Bonus Room with twin bed, washer & dryer Star Wars Room with queen bed 3 Spa-like bathroons with walk-in showers, plus Jacuzzi. Gourmet kitchen Beautiful shared backyard with private deck, BBQ grill, in-ground pool (May–August), fire pit, seating areas, and trails right outside your door!

Spacious Family 5BR Single House w/Parking

🔥 LIMITED-TIME DEAL: GET UP TO 20% OFF SELECTED DATES! ★ Entire spacious and private single-family home ★ 3 stylish living rooms with smart TV ★ 1 fully equipped kitchen + an kitchenette ★ 3 cozy dining areas ★ High-speed Wi-Fi ★ Central heating & AC ★ In-house laundry area ★ Fresh linens, towels, and essentials included ★ Parking: 2 cars in the garage + 4 reserved parking spaces A bright, roomy, and comfortable home ideal for family getaways, reunions, and group stays of up to 13 guests.

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Guest favourite

Headers’ Haven

Your family will be close to everything when you stay at this centrally-located in-law suite. Walking distance to beaches, shops, and restaurants. Steps from Steer Swamp Conservation Area. 13 miles from Boston, and an easy 10 min drive to Salem. Cool off in the pool during the summer heat, or relax in the hot tub on a chilly evening. There’s room for everyone on the pull out sectional to snuggle up for a movie night, complete with popcorn and candy machines. Sure to be a fun and cozy stay!

4br Near Stadium | Hot Tub + Firepit

Welcome to The Trophy House — your home base for fall in New England. Catch a Patriots game at nearby Gillette Stadium, spend a crisp day exploring Boston, or simply enjoy the season from the bright porch. Come home to golden-hour drinks in the patio courtyard, gather around the firepit as the air cools, then end the night soaking in the hot tub under the stars. With 4 bedrooms and room for 8, it’s made for memorable fall weekends with family and friends.

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Guest favourite

Amazing Location in Little Italy with Roof Deck

Our fully loaded one bed is centrally located in Boston's North End (Little Italy) on land that was previously American Patriot Paul Revere’s bell foundry. The unit features a spacious roof deck with a premium grill and hot tub. It is within 10 minutes walking distance to 50+ restaurants, TD Garden, the Freedom Trail, and the subway. It is also within walking distance to the Boston Common/Public Garden and many of Boston’s most visited attractions.

Luxury Scandinavian-Inspired house in Kendall

Experience modern elegance in this newly built, high-end home in the heart of Kendall Square, Cambridge. Thoughtfully designed with Scandinavian-inspired interiors. The chef’s kitchen features a Wolf gas range, Sub-Zero fridge, and Mitsubishi central air, ensuring ultimate comfort. Just minutes from MIT, the Red Line, and Lechmere Green Line, you're steps from top restaurants, cafes, and biotech hubs, with the Charles River and Beacon Hill nearby.

Top guest favourite

Guest favourite

Hot Tub, Gazebo, Pool table & Fire Table

Spacious and family-friendly home near Boston featuring a private backyard oasis with a gazebo, pool table, fire table, and outdoor dining area. Perfect for vacations, graduations, business trips, and family gatherings. Enjoy a fully equipped kitchen, fast Wi-Fi, Smart TVs, comfortable sleeping arrangements for up to 8 guests, and free driveway parking. Relax, unwind, and create lasting memories in a space designed for comfort and connection.

Romantic Getaway w/private Jacuzzi• Fire Pit•

Escape to a private romantic retreat just minutes from Boston. Relax in your private outdoor jacuzzi, enjoy the fire pit under the stars, and unwind in a cozy space designed for couples. Located in a quiet area just minutes from Boston, restaurants, and shopping — the ideal spot for couples or a peaceful weekend escape.