
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 $86 NZD per night before taxes and fees

Verified guest reviews
Over 6,640 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
30 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!
Top-rated house rentals in Winthrop
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

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.

Historic Home w/ King bd Walk to Everything
Historic home in the heart of Salem, walk to everything! Built for a painter in 1823, with sun-filled rooms, high ceilings, gleaming colonial pumpkin-pine floors; renovated for modern comfort with brand new systems. Large 1st-floor apartment in my two-family home. 5 min stroll to the center of town, witch museum, restaurants. King bed, Full bed, Queen sofa bed. Not suitable for infants or young children. Parking permit for one car only during October.
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.

Modern Smart Home/EVCharge/Boston/Harvard/MBTA
This eclectic 3-level new build modern smart home with over 3000 sq feet of living has a lot to offer! It is centrally and officially located in the Tufts/ Somerville neighborhood, near Winter Hill and is a few minutes to Boston's Back Bay. About a 15-minute walk to Magoun Square MBTA station. You and your guests will be close to many of the most popular attractions that Somerville, Cambridge and Boston has to offer.

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.

Spacious and Luxurious House
Welcome to our stunning Airbnb! Our stylish and modern ranch style home is the perfect place for your next vacation or business trip. Located in a quiet and safe neighborhood, our home is perfect for couples, families, or a group of friends. It features 3 bedrooms and bathroom and can comfortably accommodate 6 guests
Popular amenities for Winthrop house rentals
House rentals with a pool

Private heated Pool *Easy Boston Access! STR-25-22

4-Bed Home w/Pool + Walking Trails + Dead End St.

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Luxury lake retreat- pool, fire pit, trails

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

Pretzel Factory Loft w/Peloton

Best House Cambridge/Somerville

Oceanfront stunning views, train to Salem & Boston

Cozy, historic 3 bedroom home close to Boston!

Cozy & Modern Entire Residential Home ❤️

Newly remodeled home with ocean views!

Cozy & Modern 2 Bedroom House - Free Parking !

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

Hideaway House: Modern home, historic seaside town

Beach walk

Modern 2BR Getaway Near Revere Beach

Boston Buccaneer Retreat

Entire House Near Boston-Salem - Walk to the beach

Cambridge Cottage Retreat Near Harvard

Waterfront w/private beach, hot tub, & firepit!

Bright and spacious midcentury design near Boston
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $145 NZD | $164 NZD | $174 NZD | $207 NZD | $219 NZD | $236 NZD | $226 NZD | $229 NZD | $186 NZD | $196 NZD | $176 NZD | $167 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
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Atlantic City Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Waterfront rentals Winthrop
- Rentals with a patio Winthrop
- Pet-friendly rentals Winthrop
- Beachfront rentals Winthrop
- Rentals with beach access Winthrop
- Family-friendly rentals Winthrop
- Rentals with a fireplace Winthrop
- Fitness-friendly rentals Winthrop
- Apartment rentals Winthrop
- Rentals with a fire pit Winthrop
- House rentals Suffolk County
- House rentals Massachusetts
- House rentals United States
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Boston Common
- Boston Seaport
- Gillette Stadium
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- MIT Museum
- Duxbury Beach
- Boston College
- North Hampton Beach
- Northeastern University
- Crane Beach
- Quincy Market
- Tufts University
- Harvard Square
- Roger Williams Park Zoo





