House holiday rentals in Winthrop

Best House Cambridge/Somerville

spacious 1900's mansard Victorian. Bright cheerie & centrally located if you're looking for a pad in Cambridge/Somerville. A 10-12minute walk to Harvard Square & close to the Red Line. Great kitchen, living room & /cablewifi. Three bedrooms--one with a European Queen Bed, one double bed & one single. There is one full bathroom w/a large glass shower & a claw foot tub. There is a half bath on the first floor. There is a front porch to sit & sip wine on & a back deck where you can grill & eat out on. I've been living here 12 years--Its tastefully appointed, eclectic finds & a mid century modern touch--absolutely the best equipted kitchen. I've been a chef in Boston & Cambridge for quite some time!

Value · Location · Cleanliness

Private Cozy Third Floor Space

This was formerly a servant's quarters in a large colonial home on the third floor and accessed by a private stairway that leads from the first floor to the third floor. The living room and bedroom are both large with original wood floors and are appointed with a comfortable couch, chairs, full-sized bed, books, wall decorations, a big flat screen TV, private bathroom with tub and shower with all newer fixtures and there is also a small refrigerator and micro-wave. It is a totally private space.

Value · Family · Heating

Oceanfront stunning views, train to Salem & Boston

Relax at Casa de Mar, our 3 bedroom / 3 full bathroom oceanfront North Shore home with panoramic views of Swampscott Bay to Nahant. Walk to the train — downtown Salem in 7 min, Boston in 23 min. Enjoy a bright great room with 25’ ceilings, 70” TV, and modern kitchen. The master bedroom has a king bed, sitting area, TV, private balcony, and en suite bath. The first floor queen bedroom has a private balcony. The third queen bedroom has en suite bath. Perfect for family getaways and group trips.

Family · Value · Check-in

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.

Family · Value · Beach

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 six guests, making it perfect for families or groups of friends. 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 offers ample seating, and the fully equipped kitchen, private deck with breathtaking views of the ocean.

Family · Location · Outdoor spaces

Bright Family Oasis Near Boston w/ Parking

Bright, plant-filled oasis in a quiet Medford neighborhood just minutes from Boston, with easy access to transit and free parking. Guests return again and again for the spotless cleanliness, curated art, and true “home away from home” feel. Enjoy a fully equipped chef’s kitchen and private backyard. Perfect for exploring the city, then relaxing in a peaceful, beautifully designed space. Or working from home. Conveniently located for day trips to Salem, Cambridge and downtown Boston.

Family · Location · Outdoor spaces

Stunning urban hideaway nearby Harvard Square

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

Family · Value · Getting around

Boston Best with Parking - GREAT reviews

**READ our reviews :) - 10min walk to Airport Blue line subway T-stop - 10min drive to Downtown Boston - Local dining options in walking distance - 1 parking spot available upon request - Spacious and comfortable house Welcome to your Best Boston experience. I am Rafael and I will ensure that you get any attention needed with a text, call, or email. We hope that you enjoy our recommendations for activities and meals - we based them on our lifelong East Boston experiences.

Location · Value · Bathroom

Large, Comfortable & Conveniently located Home

You will be close to everything when you stay at this centrally-located private, updated historical home. 4 bedrooms & 2 baths w/plenty of extra space for large families or groups. Fenced-in spacious patio with huge backyard. Sizable, private parking area. Near Routes 95 & 128. Only 25 mins to Boston. Perfect for trips to picturesque points, including Boston, Gloucester, Newburyport, Rockport, Cape Ann, historic Salem & Maine coastal towns and cities. Dog friendly.

Family · Location · Amenities

Queen Anne Victorian in Excellent Location

3BR/2FB Queen Anne Victorian in Medford Sq/Lawrence Estates. 3 fireplaces & hardwood throughout. Open kitchen, island w/hood, marble counters & SS chef’s kitchen appliances. Mahogany deck and professionally landscaped yard. Primary BR with fireplace, primary bath;marble flrs. Location location location. Steps away from Medford Square including the Chevalier Theater; Minutes away from downtown Boston, Tufts University, Davis Square and Cambridge.

Value · Location · Getting around

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Value · Location · Cleanliness

Modern 2-bedroom w/parking near Encore and Logan

Modern two bedroom with free parking, conveniently located 7 minutes from Boston Logan Airport, 5 minutes from Revere Beach and only 12 minutes to Encore Casino and downtown Boston. No parties or events are allowed in the unit. Penalties apply. DISCLAIMER: For your safety and the safety of others, surveillance cameras are installed outdoors at this property.

Location · Family · Cleanliness