
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.

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!

Brand New 3Bed2bath Home Near Logan, Boston &Salem
Welcome to your home away from home! Enjoy a comfortable, stylish, and stress-free stay in this brand-new 3-bedroom home, perfectly located just minutes from Bostonâs most popular destinations. Whether youâre traveling with family, visiting for work, or planning a getaway, this space is designed to make you feel relaxed, welcomed, and truly at home. Youâll be just 15 minutes from Logan Airport, Downtown Boston, Salem, Revere Beach, and major highways, with the convenience of free on-site parking

Modern home 22 min Boston, 20 min Gillette Stadium
Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

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.

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.

Oceanfront 3BR/3BA near Salem + Boston w/ Views
Relax at Casa de Mar, a 3 bedroom / 3 full bathroom oceanfront North Shore home with sweeping views of Swampscott Bay to Nahant. Minutes to Salem and close to Boston. Enjoy a bright great room with 25â ceilings, 70â TV, and modern kitchen. The master bedroom features a king bed, sitting area, TV, private balcony, and en suite bath. The first floor queen bedroom includes a private balcony. The third queen bedroom has en suite bath. Perfect for family getaways and small group trips.

Sunny Salem Condo: Quiet, convenient & parking.
Enjoy historic Salem in this bright, lovely condominium on the second and third floors of a fully renovated house. Two bedrooms, two family rooms, hardwood floors, and full kitchen with major appliances, dishwasher, and a sunny table for dining. In unit washer and dryer and two parking spots in a private driveway. Walking distance to Hocus Pocus house, downtown Salem, and a great local grocery store. This location is incredibly comfortable, clean, private and relaxing.

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

Oceanfront I Decks I 4 Ensuite BRs I 35Â min to Boston
đ Welcome to Egg Rock House - âWicked awesomeâ 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 Bostonâs North Station. Relax on the front deck with sweeping ocean views just outside your door.

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.
Popular amenities for Winthrop house rentals
House rentals with a pool

Nana-tucket Inn

Pool Is Open! 4-Bed Home w/Pool + Walking Trails

Bauhaus Retreat in Nature Preserve w/ Pool

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

STEPS to Private Beach-7 Beds, Pool, Fenced Yard

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

Hidden Gem near Boston w/ Private lake access
Weekly house rentals

Boutique Beach Stay | Hull Coastal Escape

Luxury 5BR Home Minutes to Boston

Entire Home | Boston Skyline | Airport | Downtown

The House by the Sea

Spacious 5BR Executive Retreat - 10 Min to Boston

Boston Buccaneer Retreat

Cozy Cottage by the Sea

Cozy Home Walkable to Downtown
Private house rentals

My Three Suns

4BRâ˘King Bedâ˘Walk to Downtown Salemâ˘Free Parking

Bright & Cheery 4 Bedroom Home with Ocean Views

3 Bedroom Boston-area Gem

Amazing apartment

Walking Distance to Everything in Old Town

Waterfront Beach Home With Attached In- Law Suite

The Essex of Gloucester
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$17,573 GYD | G$19,874 GYD | G$21,129 GYD | G$25,104 GYD | G$26,568 GYD | G$28,660 GYD | G$27,405 GYD | G$27,823 GYD | G$22,594 GYD | G$23,849 GYD | G$21,338 GYD | G$20,292 GYD |
| 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 G$8,368Â GYD per night before taxes and fees

Verified guest reviews
Over 6,180 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 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 guestsâaveraging 4.8 out of 5!

Nearby attractions
Winthrop's top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station
Destinations to explore
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- Apartment rentals Winthrop
- Rentals with a fireplace Winthrop
- Waterfront rentals Winthrop
- Beachfront rentals Winthrop
- Rentals with beach access Winthrop
- Family-friendly rentals Winthrop
- Rentals with a patio Winthrop
- Pet-friendly rentals Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a washer and dryer Winthrop
- Fitness-friendly rentals Winthrop
- House rentals Suffolk County
- House rentals Massachusetts
- House rentals United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Gillette Stadium
- Northeastern University
- Freedom Trail
- Boston Convention and Exhibition Center
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Onset Beach
- Quincy Market
- Roxbury Crossing Station
- North Hampton Beach
- Museum of Fine Arts
- Prudential Center





