Winthrop holiday rentals

We found 2,947 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Winthrop that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winthrop

Showing deals for:25 Dec - 1 Jan

Private kitchen
Interior
Interior
Exceptional
(98 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
AU$16,994
for 7 nights, 1 home
AU$2,428 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Marina
Terrace/patio
Chestnut Sweet's front door on the garden. The Sweet is in its own building.
Interior
Exceptional
(157 reviews)

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead

8% off
AU$2,587
for 7 nights, 1 home
AU$370 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
AU$8,002
for 7 nights, 1 home
AU$1,143 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Room
Living area
Property grounds
Interior
Exceptional
(11 reviews)

Ocean front Studio across from beach

Hull

8% off
AU$3,256
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Ocean front Studio across from beach
Patio garden
Marina
Outdoor dining
Gracious staircase access to Third Floor
Exceptional
(99 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,924
for 7 nights, 1 room
AU$418 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Living room with decorative fireplace.
View of Marblehead Harbor from Fort Sewall
Bar area next to a stain-glass window.
Queen bedroom with window AC
Exceptional
(11 reviews)

Old Town Cottage Near Crocker Park and the Marblehead Harbor. Includes Parking!

Marblehead

8% off
AU$5,351
for 7 nights, 1 cottage
AU$764 per night
includes taxes & fees
Old Town Cottage Near Crocker Park and the Marblehead Harbor. Includes Parking!
Staircase from waterfront to my home
View of Spinnaker Island and water from Master Bedroom Suite
Twin bed with trundle bed in second room in Master Bedroom Suite
Portion of garden surrounding my home
Excellent
(48 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
AU$2,706
for 7 nights, 1 room
AU$387 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Sitting room
Property grounds
Kitchen
Interior
Exceptional
(21 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

8% off
AU$4,757
for 7 nights, 1 home
AU$680 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Interior
Interior
Room
Bathroom
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,957
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Living area
Living area
Room
Outdoor dining
Exceptional
(45 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,321
for 7 nights, 1 apartment
AU$1,046 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Dining
Living area
Interior
Private kitchen
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
AU$5,866
for 7 nights, 1 apartment
AU$838 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Private kitchen
Exterior detail
Living area
Interior
Exceptional
(34 reviews)

The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!

Marblehead

12% off
AU$4,934
for 7 nights, 1 home
AU$705 per night
includes taxes & fees
The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!
Dining
Private kitchen
Interior
Property grounds
Wonderful
(24 reviews)

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Boston

8% off
AU$5,727
for 7 nights, 1 apartment
AU$818 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Living area
Interior
Interior
Property grounds
Exceptional
(20 reviews)

Direct Ocean Front Condo with large wrap around balcony

Hull

8% off
AU$3,999
for 7 nights, 1 home
AU$571 per night
includes taxes & fees
Direct Ocean Front Condo with large wrap around balcony
Outdoor dining
Spacious 4 BR home for groups. Perfect for relaxing and gathering together
Room
Dining
Exceptional
(12 reviews)

4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train

Boston

8% off
AU$7,415
for 7 nights, 1 apartment
AU$1,059 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Bedroom #1
Backyard
Living room
Stainless steel kitchen appliances. (Old Table)
Exceptional
(71 reviews)

2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway

Boston

5% off
AU$3,551
for 7 nights, 1 apartment
AU$507 per night
includes taxes & fees
2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway
Dining
Interior
Interior
Room
Excellent
(7 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
AU$7,055
for 7 nights, 1 apartment
AU$1,008 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Room
Living area
Interior
Dining
Exceptional
(78 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
AU$1,416
for 7 nights, 1 room
AU$202 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Exterior detail
Living area
Room
Dining
Exceptional
(20 reviews)

Hocus Pocus Season is here! Don’t miss it!

Salem

6% off
AU$3,178
for 7 nights, 1 apartment
AU$454 per night
includes taxes & fees
Hocus Pocus Season is here! Don’t miss it!
Living area
Living area
Dining
Hallway between bedrooms, kitchen & bathroom
Exceptional
(11 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

8% off
AU$5,222
for 7 nights, 1 apartment
AU$746 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Room
Private kitchen
Exterior
Living area
Exceptional
(32 reviews)

Moody Salem Home Away From Home

Salem

8% off
AU$2,788
for 7 nights, 1 home
AU$398 per night
includes taxes & fees
Moody Salem Home Away From Home
Laundry in property
Private kitchen
Room
Overview
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
AU$4,210
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Living area
Dining
Living area
Private kitchen
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,094
for 7 nights, 1 apartment
AU$728 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Interior
Dining
Living area
Outdoor dining
Exceptional
(42 reviews)

Samuel Tucker House - Downtown Luxury 2 Bedroom Condo

Marblehead

7% off
AU$2,806
for 7 nights, 1 apartment
AU$401 per night
includes taxes & fees
Samuel Tucker House - Downtown Luxury 2 Bedroom Condo

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The beachside setting of Winthrop is ready to explore

The beaches and other outdoor surroundings create an inviting atmosphere in Winthrop. Travellers appreciate the restaurants in this welcoming city. Fenway Park and Boston Harbor are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Winthrop

Do you want to discover top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that Winthrop has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (4.7 mi / 7.5 km)
  • Harpoon Brewery (3.5 mi / 5.6 km)
  • New England Aquarium (3.7 mi / 6 km)
  • LEGO® Discovery Center Boston (5.2 mi / 8.3 km)
  • Boston Marathon Finish Line (5.3 mi / 8.6 km)
  • Franklin Park Zoo (7.5 mi / 12 km)

Exploring the natural features in Winthrop

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Winthrop. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (4.6 mi / 7.4 km)
  • Boston Harbor (3.7 mi / 5.9 km)
  • Copley Square (5.2 mi / 8.4 km)
  • Revere Beach (1.9 mi / 3 km)
  • Castle Island (3.2 mi / 5.2 km)
  • Seaport Common (3.7 mi / 6 km)

Seasonal weather averages in Winthrop

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 21°C.

Transport to and around Winthrop

The nearest airport is in Logan International Airport (BOS), located 2.1 mi (3.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 2.7 mi (4.3 km) away.

Frequently asked questions

What is the best area to stay in Winthrop when booking a holiday rental?
When considering a holiday rental in Winthrop, Massachusetts, a popular area to stay is near the waterfront, particularly in the neighbourhoods that offer stunning views of Boston Harbour. This location not only provides easy access to beautiful beaches but also the scenic charm of coastal living.The area boasts various properties, ranging from quaint cottages to more modern rentals, making it suitable for different preferences and budgets. Staying close to the waterfront allows visitors to enjoy top attractions such as Winthrop Beach, where you can relax by the sea or take a leisurely stroll along the shore. Additionally, the historic Winthrop Town Centre is nearby, offering a delightful mix of independent shops, cafes, and eateries that reflect the local character.Another appealing neighbourhood is the one that surrounds the Winthrop Yacht Club, which is great for those interested in water activities. This area not only provides easy access to boating and sailing but also features picturesque views, making it an inviting place to unwind after a day of exploration.
Where are the best areas for renting a beach house in Winthrop?
For renting a beach house in Winthrop, consider the picturesque waterfront areas along the eastern coast of Massachusetts. The neighbourhoods near Winthrop Beach offer a selection of charming properties with convenient access to the sandy shores and stunning views of Boston Harbour. Many of these beach houses come equipped with amenities such as outdoor patios or decks, where guests can enjoy al fresco dining, as well as fully stocked kitchens that cater to families or groups looking to make the most of their seaside experience.In addition, properties around Point Shirley provide a more tranquil environment, often featuring private yards and direct beach access, superb for leisurely strolls along the coast. The local area is also home to parks and walking paths, enhancing the outdoor experience. Many of the rentals here may include features like air conditioning, Wi-Fi, and laundry facilities, ensuring comfort during your stay.Furthermore, the proximity to local shops and restaurants in the nearby town centre adds convenience for visitors, making it easy to explore the vibrant local culture and cuisine.
What is the most popular type of holiday rental accomodation in Winthrop?
In Winthrop, apartments are the most popular type of holiday rental, with about 36 available throughout the town. These apartments often feature amenities such as fully equipped kitchens, comfortable living areas, and some may include balconies with views of the surrounding area. They are typically located in convenient neighbourhoods, providing easy access to local attractions and the waterfront.In addition to apartments, there are several holiday houses available for those seeking more space, ideal for families or groups. These homes usually come with multiple bedrooms, private outdoor areas, and amenities such as BBQ facilities, making them great for larger gatherings.
Are there any family house rentals in Winthrop?
In Winthrop, Massachusetts, there are several family-friendly house rentals available, making it a great spot for families looking to enjoy coastal living. Many of these homes are situated close to the beach, providing easy access for sandcastle building and seaside picnics. Properties often feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces like decks or patios where children can play safely.The town's proximity to local parks and playgrounds adds to its appeal, giving families plenty of options for outdoor activities. Additionally, visitors can explore the charming neighbourhoods, with their quaint shops and restaurants, creating a friendly setting for everyone.
Can I rent a holiday home with a pool or hot tub in Winthrop?
In Winthrop, there are several holiday homes available for rent that come with pools or hot tubs, providing a great option for travellers looking to relax and unwind during their stay. This charming coastal town, located just a short drive from Boston, offers a mix of beachside living and local amenities. Many of the holiday rentals feature private pools, inviting hot tubs, and outdoor spaces great for family gatherings or leisurely afternoons. Additionally, fully equipped kitchens and comfortable living areas are common, allowing guests to enjoy a cozy feel.
Are there pet-friendly house rentals in Winthrop?
In Winthrop, there are several pet-friendly holiday house rentals available, making it a welcoming destination for travellers with pets. The area features charming homes that often come equipped with amenities such as fully stocked kitchens, private outdoor spaces, and comfortable living rooms, great for relaxing after a day of exploring.Winthrop's proximity to scenic waterfront parks, such as Winthrop Beach and Deer Island, provides ample opportunities for pet owners to enjoy leisurely walks and outdoor activities with their furry companions. Additionally, the local community is known for its pet-friendly atmosphere, with various cafes and shops that welcome pets, enhancing the overall experience for travellers.
Are there any remote work holiday rentals in Winthrop?
In Winthrop, there are around 40 holiday rentals that cater to remote work needs. This coastal town, located just a short distance from Boston, offers a variety of properties that provide essential amenities for those looking to work while enjoying a getaway. Many of these rentals come equipped with reliable Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living spaces conducive to productivity.The area itself is charming, with scenic views of the waterfront and easy access to local parks. After a day of work, you can explore Winthrop's lovely beaches or enjoy the nearby restaurants and cafes. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winthrop?
In Winthrop, popular rental amenities include a kitchen, which allows guests to prepare their own meals, and a coffee and tea maker for a comforting morning brew. Many properties also offer onsite parking, making it convenient for those travelling by car. A desk is available in several rentals, providing a workspace for guests who may need to catch up on business or studies. Additionally, the proximity to the beach enhances the appeal of these rentals, allowing visitors to enjoy seaside activities and relaxation.
When is the best time to visit Winthrop for a holiday rental?
July marks the peak time to visit Winthrop, where sun-seekers flock to enjoy the charming coastal atmosphere. This period, from May to July, offers the best weather for beach activities, with pleasant temperatures averaging around 20 to 30 degrees Celsius. Visitors can indulge in swimming, sunbathing, and exploring the beautiful waterfront, all while soaking up the vibrant summer vibe.July is particularly bustling, making it an exciting choice for those who thrive in lively environments filled with fellow holidaymakers. The local restaurants and cafes buzz with energy, and various summer events add to the festive spirit.For those looking for a more budget-friendly option, consider planning your trip around November. During this time, this month provides a unique opportunity to experience Winthrop's coastal charm without the crowds. You can enjoy peaceful walks along the beach and capture stunning photographs of the tranquil landscape.Ultimately, your choice of when to visit Winthrop will depend on whether you prefer the vibrant energy of peak season or the serene beauty of the off-peak months.
What are the top attractions in Winthrop?
In Winthrop, visitors can enjoy a variety of attractions that showcase the town's coastal charm and community spirit. The picturesque Winthrop Beach offers a lovely seaside experience, great for leisurely walks and enjoying the ocean views. Close to the beach, the Winthrop Lighthouse stands as a historic landmark, providing a lovely backdrop for photographs and a glimpse into the area's maritime history.The quaint town centre features a selection of local shops, cafes, and restaurants, where travellers can savour fresh seafood and other regional delicacies. For outdoor enthusiasts, the Belle Isle Marsh Reservation provides walking trails and opportunities for birdwatching, allowing visitors to connect with nature.Additionally, the nearby Deer Island offers scenic views of the Boston skyline and is accessible for walking and biking, making it a great spot for a day out.
Are all fees included in the Winthrop holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winthrop holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winthrop with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winthrop holiday homes?
You can find great discounts on holiday homes in Winthrop on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winthrop holiday home booking on Stayz?
To find Winthrop holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winthrop?
A long-stay holiday home in Winthrop is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winthrop holiday home?
Book your Winthrop holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winthrop?
Prices for holiday homes in Winthrop vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winthrop to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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