
House holiday rentals in Winthrop
Find and book unique houses on Airbnb
Quick stats about house rentals in Winthrop

Total holiday rentals
Explore 60 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at $68 NZD per night before taxes and fees

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

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Winthrop holiday 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
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 Boston’s most popular destinations. Whether you’re traveling with family, visiting for work, or planning a getaway, this space is designed to make you feel relaxed, welcomed, and truly at home. You’ll 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.

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.

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 25’ ceilings, 70” TV, and modern kitchen. The master bedroom features a king bed, sitting area, 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.

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.

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.

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!

Getaway in Historic Charlestown
**PLEASE NOTE REGARDING PARKING" Resident sticker parking 8 am to 8 pm Monday thru Friday. Weekends and holidays, no restrictions. The automobile has to be registered in Charlestown to get a parking sticker. The first floor of a three-story wooden framed home, built-in 1875. A totally private space. There is a good-sized living room, a bedroom with a queen size sleigh bed, and a full kitchen. The 'cozy' bathroom was added in 2012. Maximum of TWO people.
Popular amenities for Winthrop house rentals
House rentals with a pool

Summer heated Pool ~Easy Boston Access! STR-25-22

Pool Is Open! 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

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)
Weekly house rentals

Boutique Beach Stay | Hull Coastal Escape

Entire Home | Boston Skyline | Airport | Downtown

Modern 2BR Getaway Near Revere Beach

Beach walk

Boston Buccaneer Retreat

Entire House Near Boston-Salem - Walk to the beach

Magnificent Ocean View; walk to beaches and town

3 bdr, steps from the ocean, minutes from Boston
Private house rentals

Luxury 5BR Home Steps to Medford Square

The House by the Sea

3 Bedroom Boston-area Gem

Cozy Cottage by the Sea

Cozy Home Walkable to Downtown

Dotey Cottage: Walk to the Beach w/ Fenced in Yard

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

Lovely home by the Ocean-4 miles from Salem
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $143 NZD | $162 NZD | $172 NZD | $205 NZD | $217 NZD | $234 NZD | $223 NZD | $227 NZD | $184 NZD | $194 NZD | $174 NZD | $165 NZD |
| 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 |
Destinations to explore
- Plainview Holiday rentals
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- Boston Holiday rentals
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- Waterfront rentals Winthrop
- Rentals with a fireplace Winthrop
- Rentals with beach access Winthrop
- Apartment rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with outdoor seating Winthrop
- Beachfront rentals Winthrop
- Family-friendly rentals Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- Fitness-friendly rentals Winthrop
- House rentals Suffolk County
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- 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
- Northeastern University
- Gillette Stadium
- 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





