
House holiday rentals in Winthrop
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Top-rated house rentals in Winthrop
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The Nest | A peaceful retreat in the city
Unwind and relax on a quiet street in the heart of Somerville. With easy access to Harvard, MIT, Tufts, and Boston, this newly updated Victorian home is a perfect base to explore all that New England has to offer. You can also visit an abundance of local restaurants and coffeeshops within walking distance. During your stay, you will enjoy full use of a smart TV, comfortable work-from-home setup, brand new washer/dryer/dishwasher/range, off-street parking, and multizone heating/ cooling systems.

Seaside Cottage
Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

Family Friendly Green Oasis Minutes from Boston
Oasis filled with natural light, plants & art in a quiet neighborhood minutes from Downtown Boston. Perfect for sightseeing & enjoying the best of the city and neighboring towns. Walk to Wrights Pond for a swim & hike the Middlesex Fellsway Reservation. Fully equipped chefs kitchen. Private backyard surrounded by trees. Wake up to birds chirping and relax after a long day of exploring while you watch your favorite TV show. Enjoy a bath in the soak-in tub. 3 parking spaces, office setup & laundry

3 BR Private Family Home, S. Boston/Seaport/BCEC
A beautiful, renovated single home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features luxurious amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

Ocean Views at Casa de Mar near Salem & Boston
Relax and unwind at Casa de Mar - our 3 bed, 3 full bath seaside home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, a desk, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

Gorgeous Retreat - Amazing Kitchen - Hosts 6
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino Whether you travel for outdoor adventure, beach time, family bonding or just hanging out, this gorgeous two-bedroom home – just minutes away from the beach and Encore Casino and less than 20 minutes from the city center – was lovingly renovated and outfitted to curate an experience of being at home, at peace, and surrounded with quiet beauty. Restaurants, Grocery Store, Pharmacy and other conveniences within minutes walk.

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.

Entire Apartment in Stoneham
Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

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.

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free
Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Prime location near Boston
Home in Everett, MA. Located just a 20 minute walk from Encore Boston Harbor Casino. This location is also just a 15 minute drive from downtown Boston. Room in the basement has a microwave, refrigerator, coffee maker, and hot water for making tea which is provided along with light snacks and coffee. There is a desk for laptop. Queen Tempurpedic Mattress topper as well as a pull out sofa. Private bathroom with spacious shower. See guide book for more info on the area!

Beautiful historical house in Salem
The whole group will enjoy easy access to everything from this centrally located place. A few minutes walk to a multitude of great restaurants, shops, galleries, the witch house, ghost and witch tours, trolley tours, Salem ferry, Pickering wharf, Salem witch museum, witch dungeon museum and a few minutes drive to Salem Willows and the house of the seven gables. All three bedrooms that are on the second floor will have AC units from mid June till September.
Popular amenities for Winthrop house rentals
House rentals with a pool

NEW! Walk To Beach! Sunshine House

Comfortable Home w/ POOL!

Large Pool, Nature Trails, Redd's Pond, 4-Bed

Bauhaus Retreat in Nature Preserve

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

Large & beautiful home, shared pool and yard
Weekly house rentals

Spacious & Pet-Friendly Modern Home in Charlestown

All the comforts of home, quiet city neighborhood

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

Sunny 3 bedroom on beach

Harvard Square - free permitted on street parking

Sea Forever - Oceanfront Home in Nahant!

Cozy & Modern Entire Residential Home ❤️

Newly remodeled home with ocean views!
Private house rentals

Cozy by the coast! Long Term deals!

Lux Townhouse Steps to T, Zen Patio + 4 Parking

Safe Harbor At Sunset Point With a View

Entire House Near Boston-Salem - Walk to the beach

*NEW*Free Parking|Steps to Train|Game Room+Poker

Revere Beach House, Logan Airport, Bay Views

Minot's Delight

Across the Subway · close to TD Garden · Families!
Quick stats about house rentals in Winthrop
Total rentals
60 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
6.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
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- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- Duxbury Beach
- New England Aquarium
- Good Harbor Beach
- Canobie Lake Park
- MIT Museum
- Freedom Trail
- Crane Beach
- Faneuil Hall Marketplace
- Onset Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- North Hampton Beach
- Rye North Beach
- Quincy Market
- Prudential Center
- White Horse Beach