
House holiday 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!

Seaside Cottage
Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

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!

Homey getaway by the beach
Cute and homey well furnished 3 bedroom apartment in an older 2 family beach house. 1 min walk away from the best and least crowded part of Nantasket Beach, and a short 5 min drive from the Hull downtown. Ideal for vacationers, visitors, and families, the house features 3 bedrooms, 2 full baths, a nice and well equip kitchen with quality Samsung appliances, and a small BBQ deck overlooking a private backyard with a picnic table and stone patio. The house is literally 175 Yards from the beach :-)

Gorgeous Retreat - Amazing Kitchen - Hosts 6
PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino Whether you travel for outdoor adventure, beach time, family bonding or just hanging out, this gorgeous two-bedroom home – just minutes away from the beach and Encore Casino and less than 20 minutes from the city center – was lovingly renovated and outfitted to curate an experience of being at home, at peace, and surrounded with quiet beauty. Restaurants, Grocery Store, Pharmacy and other conveniences within minutes walk.

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.

Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

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.

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.

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.

The Brickhouz at Arlington !
Just a little bit of everything for everyone to have a spectacular time in Boston, perfect for family gathering ! A funky and quirky cozy 4-bedroom brickhouse smack right in the middle of Arlington Center. 10 mins to Harvard Square, 15 minutes to Boston and Logan airport. Sleeps 8 - 2 bathrooms. Short 1 minute walk to cafes and restaurants. Discounts available for longer stays. Strictly no parties or unapproved pets.
Popular amenities for house rentals in Winthrop
House rentals with a pool

Entire Cape House

Dog-Friendly, 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

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

The House by the Sea

Coastal Getaway: walk to beach and town

Cozy & Modern Entire Residential Home ❤️

Historic Home w/ King bd Walk to Everything

Newly remodeled home with ocean views!

3 bdr, steps from the ocean, minutes from Boston

Lovely home by the Ocean-4 miles from Salem
Private house rentals

Charming upscale apartment

My Three Suns

Hideaway House: Modern home, historic seaside town

4BR•King Bed•Walk to Downtown Salem•Free Parking

Modern 2BR Getaway Near Revere Beach

Sea Forever - Oceanfront Home in Nahant!

Entire House Near Boston-Salem - Walk to the beach

Steps to beach -18 min to Boston, Sleeps 8
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 SGD | $122 SGD | $125 SGD | $153 SGD | $162 SGD | $174 SGD | $167 SGD | $169 SGD | $138 SGD | $145 SGD | $130 SGD | $124 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 house rentals in Winthrop

Total holiday rentals
Explore 60 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at $51 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 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 Station and Suffolk Downs Station
Destinations to explore
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- Rentals with a patio Winthrop
- Rentals with outdoor seating Winthrop
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- Rentals with a fireplace Winthrop
- Pet-friendly rentals Winthrop
- Beachfront rentals Winthrop
- Family-friendly rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- House rentals Suffolk County
- House rentals Massachusetts
- House rentals United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Northeastern University
- Boston Seaport
- Boston University
- Freedom Trail
- MIT Museum
- New England Aquarium
- Boston Convention and Exhibition Center
- Gillette Stadium
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Quincy Market
- Museum of Fine Arts
- Onset Beach
- North Hampton Beach
- Roxbury Crossing Station
- Prudential Center




