
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 $64 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Winthrop holiday rentals include wifi 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 (MBTA 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!
ValueLocationBathroom

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.
FamilyLocationHospitality

Oceanfront stunning views, train to Salem & Boston
Relax at Casa de Mar, our 3 bedroom / 3 full bathroom oceanfront North Shore home with panoramic views of Swampscott Bay to Nahant. Walk to the train — downtown Salem in 7 min, Boston in 23 min. Enjoy a bright great room with 25’ ceilings, 70” TV, and modern kitchen. The master bedroom has a king bed, sitting area, TV, private balcony, and en suite bath. The first floor queen bedroom has a private balcony. The third queen bedroom has en suite bath. Perfect for family getaways and group trips.
LocationFamilyQuiet

Cozy, Spacious Home in the Heart of Cambridge
Welcome to your home away from home in the heart of Cambridge! This spacious 4bd/2ba home is perfect for family visits, getaways with friends, and long-term stays. House-trained pets are welcome! We are very conveniently located in Central Square: <5 min walk from H Mart, Target, CVS, restaurants, cafes <5 min walk from the Central T station and bus stop 1 stop/15 min walk from MIT/Kendall Square 1 stop/20 min walk from Harvard University 3 stops/15 min ride from Boston Common/Downtown Boston
FamilyLocationComfort

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.
FamilyValueTV

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.
LocationValuePets

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.
LocationFamilyNearby

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.
FamilyValueAccuracy

Beautiful Kitchen | Deck | Yard | Salem/Marblehead
This charming and recently renovated 3-bedroom, 1.5-bathroom house is the perfect retreat for your New England family getaway. Nestled directly between historic Marblehead and Salem downtown, you'll find yourself surrounded by the rich maritime history and colonial charm that these picturesque towns have to offer. Enjoy charming downtown Marblehead or enjoy the bewitching ambiance in Salem. Come home to glass of wine on the deck while the kids play freely in the backyard.
ValueFamilyBack garden

10 minutes to Airport-Boston-Casino (2G)
(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.
FamilyLocationWalkability
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.
ValueLocationLaundry

Rio Stays
Our place is your place with a combination of modern and colonial touches, we made it thinking about you, either for fun, recreation or business, close to the casino, downtown, revere beach, and the most prestigious colleges and universities, and don't forget museums and historical places, with amazing places, with a great night and day view , and coffee maker to start or finish your day!!
LocationFamilyBathroom
Popular amenities for house rentals in Winthrop
House rentals with a pool

Spacious vacation unit in premium suburban town
ValueFamilyParks

Theatre | Arcade | Pool w. Free 3 Car Parking
LocationFamilyKitchen

Pool is Open in Sept.+Walking Trails+Dead End St.
FamilyValueBathroom

Beautiful Spacious 4BRM House!
FamilyValueCheck-in

Heated Pool Firepit Huge Screen Porch King bed
LocationFamilyBathroom

the house of id; vintage shop, accessible space
FamilyLocationAccuracy

Private/Quiet Single Family Home
ValueLocationBathroom

Luxury lake retreat- pool, fire pit, trails
ValueFamilyAmenities
Weekly house rentals

The Brickhouz at Arlington !
FamilyLocationHeating

Oceanfront I Decks I 4 Ensuite BRs I 35 min Boston
LocationValueShared spaces

Walk To Everything
ValueFamilyHospitality

Cozy, historic 3 bedroom home close to Boston!
FamilyLocationAccuracy

Prime location near Boston
ValueFamilyHospitality

Luxurious House-Harvard/PorterT 4BR/4Bath, Parking
FamilyLocationEV charging

Large, Comfortable & Conveniently located Home
LocationFamilyAir conditioning

Top 10% Stay | Sleeps 6 | Easy Boston Access
FamilyValueParking
Private house rentals

3 bdr, steps from the ocean, minutes from Boston
ValueFamilyHospitality

Waterfront Escape - Close to Airport & Downtown
ValueLocationNearby

The Beach House, Crescent Beach
LocationFamilyCheck-in

Modern 2BR Getaway Near Revere Beach
ValueFamilyParking

Cambridge Cottage Retreat Near Harvard
FamilyLocationComfort

Seaside Serenity
LocationFamilyCleanliness

Magnificent Ocean View; walk to beaches and town
FamilyLocationSleep quality

SkyDeck Stylish Stay
FamilyLocationComfort
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 SGD | $121 SGD | $128 SGD | $158 SGD | $147 SGD | $191 SGD | $167 SGD | $169 SGD | $137 SGD | $145 SGD | $130 SGD | $123 SGD |
| 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
- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- Boston College
- Northeastern University
- MIT Museum
- Duxbury Beach
- North Hampton Beach
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Roger Williams Park Zoo





