
Apartment holiday rentals in Winthrop
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Winthrop
Guests agree: these apartments are highly rated for location, cleanliness and more.

Walk! Walk! Kenmore Square - 2 Beds / 1 Bathroom
2 beds / 1 bathroom apartment in the middle of everything! Located right in Kenmore Square, steps from subway station and Famous Citgo Sign. Walking distance to Fenway Park, Back Bay, restaurants, bars, and more! Walk walk walk everywhere! Next to Boston University and in front of Charles River Esplanade. Very close to Downtown, Cambridge, Longwood Medical Area, supermarkets, and way so many cool places! Includes everything you'll need for your stay. Super safe and convenient neighborhood! :)

Oceanfront Pool. Close to Boston. Free Parking.
Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Country Charm minutes from the Hub - 1st Floor Apt
Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Spacious 3 Bedroom Apartment with King Bed
Family friendly, walk-out basement style apartment close to everything! Clean and safe neighborhood. A 10 minute walk to two beaches: Revere Beach - America's first public beach & Short Beach - a neighborhood favorite. 5 minute walk to Beachmont T station and bus lines - 15 minutes to Downtown Boston! 10 minute drive to Logan or 20 minute drive to the Casino. 25 minute drive to Salem. Walkable to an Italian Bakery, Dunkin Donuts and Starbucks as well as a number of restaurants and eateries.

Beachmont Guest Suite
Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

Stunning Oceanview-4 Train Stop Logan Airport
Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

Modern & Cozy Apt close to Boston and Salem
New & Modern, Close to the beach , 15 minutes to the airport & BOSTON. Close to the beach, Salem, & Boston. minutes away from the commuter rail 5 People can comfortably stay here. minutes away from the commuter rail 10 minutes away from Salem 15 minutes to the Airport Several basic amenities included like snacks, water, mouthwash, toothbrushes, toothpastes, etc. Washing and Drying machine are included in the stay. Free Parking (Private Driveway) Smart TV with Netflix access included

Spacious Strawberry Hill Suite (West Cambridge)
This 3rd floor suite is less than 2 miles west of Harvard Sq. You'll have exclusive access to the space, which has a full bathroom and kitchenette. There is a queen bed suitable for two people and the couch in the living room converts to a bed for one. Our neighborhood is friendly, safe, and has a lot to offer. Public transportation (bus) is a 5 minute walk. The trip to Harvard Square is 10-15 minutes. I live in the home downstairs and am available should you need me during your stay.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

2 Bedroom Apartment with Ocean Views
Quiet, newly renovated 2 bedroom apartment just outside Boston 180 degree ocean views 10-15 min walk to subway with quick access to Goverment Center, MGH, Aquarium, North End and TD Garden. Beach access accross the street and short walk to Revere Beach. Lots of good resturaunts and cafes nearby. Unit is located on the 3rd floor. 3 sets of stairs to access apartment. Perfectly safe but not handicap accessible or convenient for anyone with impaired mobility or small children.

-0 Garden Apt 2 BR Free Parkng Near Airprt/Boston
Our newly renovated condo was gutted down to the studs and totally rebuilt with high-end finishes. There is plenty of space for guests to sit, relax, and mingle. The kitchen is equipped with stainless-steel appliances and select tools to cook a hearty meal before heading out for the day. The beds are fitted with cotton sheets for a comfortable restful sleep. Please see our other listings http://abnb.me/EVmg/eyPnXsHpyD http://abnb.me/EVmg/VTw1o92pyD

Entire guest suite in Stoneham
Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.
Popular amenities for Winthrop apartment rentals
Weekly apartment rentals

Spacious 2B Entire Home near Boston, Salem& Encore

Pleasant Place 2

Boston / Charlestown Apartment

Quiet brownstone close to city

Prime Central 1brm in North End Boston

Nxt to ocean, 5 min dntwn by T

5 minutes to downtown. Charming. Clean. Cozy.

Lux 2BR Apt w/ Pool and Gym
Private apartment rentals

1 bed, 2 rooms, 4 guests Cute&new. Free parking

The Upton - The Upton Boston, South End

Beacon Hills Studio next to State house

Studio in East Boston #1

Ocean view studio with hot tub & access to Boston

Luxury Boston Home +Free Parking +5 mins to Casino

Chic Condo near T Station & Airport.

The Family House - 3 Bedroom Condo with Parking
Apartment rentals with a hot tub

South Boston. Minutes away from Convention Center

c. 1850 Farmhouse 8mi. from Boston-close to Salem

Lakeside apartment, patio, hot tub, outside shower

Renovated Studio, steps to MGH, Suffolk, Sleeps 4

Two Bedroom Apt Pool Gym, Free Parking.

Cozy Waterfront Home with Jacuzzi and Fireplace

Studio Apt private bath+ Hot Tub, free parking

Amazing Location in Little Italy with Roof Deck
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $164 SGD | $183 SGD | $208 SGD | $211 SGD | $250 SGD | $227 SGD | $253 SGD | $255 SGD | $237 SGD | $253 SGD | $206 SGD | $182 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 |
Quick stats about flat rentals in Winthrop

Total holiday rentals
Explore 90 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at $63 SGD per night before taxes and fees

Verified guest reviews
Over 5,260 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
80 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 Station and Suffolk Downs Station
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Waterfront rentals Winthrop
- Rentals with outdoor seating Winthrop
- Rentals with a patio Winthrop
- Pet-friendly rentals Winthrop
- Fitness-friendly rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- Rentals with beach access Winthrop
- Family-friendly rentals Winthrop
- Rentals with a fireplace Winthrop
- Beachfront rentals Winthrop
- House rentals Winthrop
- Flat rentals Suffolk County
- Flat rentals Massachusetts
- Flat rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Boston University
- Boston Seaport
- Canobie Lake Park
- Crane Beach
- Boston Convention and Exhibition Center
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- Gillette Stadium
- Onset Beach
- North Hampton Beach
- Prudential Center
- Roger Williams Park Zoo
- Roxbury Crossing Station




