
House vacation rentals in Winthrop
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Top-rated house rentals in Winthrop
Guests agree: these houses are highly rated for location, cleanliness, and more.

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

Retro New England cottage - walk to the beach!
A peaceful beach retreat close to all the action. This one-bedroom bungalow is one of the oldest in the neighborhood and is full of retro charm. The house is within walking distance of Nantasket Beach and is set back from the road in a large, quiet yard. The driveway is big enough to park two cars, so you'll never have to worry about beach parking. Enjoy all Hull has to offer, from fresh seafood to nature reserves and paddleboarding. Convenient ferry access makes a day trip to Boston a breeze.

Homey getaway by the beach
Cute and homey well furnished 3 bedroom apartment in an older 2 family beach house. 1 min walk away from the best and least crowded part of Nantasket Beach, and a short 5 min drive from the Hull downtown. Ideal for vacationers, visitors, and families, the house features 3 bedrooms, 2 full baths, a nice and well equip kitchen with quality Samsung appliances, and a small BBQ deck overlooking a private backyard with a picnic table and stone patio. The house is literally 175 Yards from the beach :-)

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.

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.

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.

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.

Clean, spacious In-Law Suite -Near Everything
Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

By the Ocean - Egg Rock House - 4 bed 4.5 bath
🐚 Welcome to Egg Rock House - “Wicked awesome” oceanfront home on the scenic shores of New England. Steps to restaurants, shops, nightlife, trains, and endless outdoor fun. Perfect launchpad for visiting Ipswich, Newburyport, Salem, Marblehead, Gloucester, and Rockport. Only 30 minutes by train to Boston’s North Station. Relax on the front deck with sweeping ocean views just outside your door.

Walk To Everything
NOTE FOR WORLD CUP 2026 TRAVELERS: Please be advised this property is not near Foxborough, MA. Roughly 1 1/2-2hrs by car. Much longer by public transportation. Steps from the harbor and minutes to the beach, this modern two-bedroom home has been completely renovated. Free parking on site and surrounded by shopping, food, and more--walking distance to everything you need.
Popular amenities for Winthrop house rentals
House rentals with a pool

Nana-tucket Inn

Entire Cape House

Dog-Friendly, 4-Bed Home w/Pool, Walking Trails

Bauhaus Retreat in Nature Preserve w/ Pool

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Private 4BR Home w/ Pool | Family Friendly Retreat

Spacious vacation unit in premium suburban town
Weekly house rentals

Spacious & Pet-Friendly Modern Home in Charlestown

Charming upscale apartment

My Three Suns

Entire Home 2BR/2BTH Quite Area with parking

Bright & Cheery 4 Bedroom Home with Ocean Views

Amazing apartment

Entire House Near Boston-Salem - Walk to the beach

Beautiful Kitchen | Deck | Yard | Salem/Marblehead
Private house rentals

Boutique Beach Stay | Hull Coastal Escape

4BR•King Bed•Walk to Downtown Salem•Free Parking

The House by the Sea

3 Bedroom Boston-area Gem

Villaggio By The Sea.

Coastal Getaway: walk to beach and town

Oceanfront-Harbor View Home

The Sunset Lighthouse Marblehead
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ308 | ﺩ.ﺇ353 | ﺩ.ﺇ360 | ﺩ.ﺇ441 | ﺩ.ﺇ466 | ﺩ.ﺇ503 | ﺩ.ﺇ481 | ﺩ.ﺇ488 | ﺩ.ﺇ397 | ﺩ.ﺇ419 | ﺩ.ﺇ375 | ﺩ.ﺇ356 |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about house rentals in Winthrop

Total vacation rentals
Explore 60 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 5,950 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Winthrop vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winthrop rentals

4.8 Average rating
Winthrop stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Winthrop's top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station
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- Rentals with a patio Winthrop
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- Rentals with a washer and dryer Winthrop
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- Family-friendly rentals Winthrop
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Boston Seaport
- Boston University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Boston Convention and Exhibition Center
- Canobie Lake Park
- Gillette Stadium
- Crane Beach
- Duxbury Beach
- Quincy Market
- Museum of Fine Arts
- Onset Beach
- North Hampton Beach
- Roxbury Crossing Station
- Prudential Center
- Roger Williams Park Zoo




