Winthrop holiday rentals

We found 3,038 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:13 Nov - 20 Nov

Dining
Private kitchen
Interior
Exceptional
(90 reviews)

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

Boston

8% off
AU$17,435
for 7 nights, 1 home
AU$2,491 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Private kitchen
Living area
Room
Living area
Exceptional
(39 reviews)

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

Boston

8% off
AU$7,706
for 7 nights, 1 apartment
AU$1,101 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Private kitchen
Exterior detail
Room
Living area
Exceptional
(28 reviews)

Funky and cozy home ! A little bit of everything for everyone.

Arlington

8% off
AU$5,342
for 7 nights, 1 home
AU$763 per night
includes taxes & fees
Funky and cozy home ! A little bit of everything for everyone.
Chestnut Sweet's front door on the garden. The Sweet is in its own building.
Terrace/patio
Interior
The garden
Exceptional
(152 reviews)

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

Marblehead

8% off
AU$2,548
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Outdoor dining
Marina
View of waterfront from Third Floor Suite Living Room
Gracious staircase access to Third Floor
Exceptional
(97 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,909
for 7 nights, 1 room
AU$416 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Living room, 65" Smart TV, Genuine leather sectional sofa, Book and toys shelf.
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Exceptional
(66 reviews)

Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite

Boston

8% off
AU$7,649
for 7 nights, 1 apartment
AU$1,093 per night
includes taxes & fees
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Entrance to the cottage.
Kitchen and dining area with access to the back deck.
Kitchen with round dining table that seats four.
Living room with adjacent bar area.
Exceptional
(9 reviews)

Adorable Boat House with Covered Deck, Courtyard and Office. Pet-friendly

Marblehead

8% off
AU$4,712
for 7 nights, 1 cottage
AU$673 per night
includes taxes & fees
Adorable Boat House with Covered Deck, Courtyard and Office. Pet-friendly
Interior
Interior
Living area
Property grounds
Exceptional
(17 reviews)

Direct Ocean Front Condo with large wrap around balcony

Hull

8% off
AU$4,224
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
Direct Ocean Front Condo with large wrap around balcony
Interior
Property grounds
Sitting room
Exterior detail
Exceptional
(19 reviews)

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

Cambridge

8% off
AU$4,734
for 7 nights, 1 home
AU$676 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Dining
Exterior detail
Living area
Interior
Exceptional
(33 reviews)

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

Marblehead

12% off
AU$4,860
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!
Interior
Interior
Room
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,928
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Living room with decorative fireplace.
View of Marblehead Harbor from Fort Sewall
Bar area next to a stain-glass window.
Living room with smart TV.
Exceptional
(9 reviews)

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

Marblehead

8% off
AU$3,839
for 7 nights, 1 cottage
AU$548 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
Portion of garden surrounding my home
Twin bed with trundle bed in second room in Master Bedroom Suite
Excellent
(46 reviews)

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

Hull

8% off
AU$2,693
for 7 nights, 1 room
AU$385 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Property grounds
Living area
Room
Private kitchen
Exceptional
(6 reviews)

Ocean front Studio across from beach

Hull

8% off
AU$2,788
for 7 nights, 1 home
AU$398 per night
includes taxes & fees
Ocean front Studio across from beach
Top floor, with queen sized bed and seating.
Exterior
Terrace/patio
Relax on the main floor, up one level and adjacent to the kitchen, with balcony.
Exceptional
(8 reviews)

Relaxing 2-BR townhome steps to MIT, Harvard, T Red Line, food & more!

Cambridge

8% off
AU$4,147
for 7 nights, 1 home
AU$592 per night
includes taxes & fees
Relaxing 2-BR townhome steps to MIT, Harvard, T Red Line, food & more!
Interior
Interior
Room
Dining
Very good
(6 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
AU$7,021
for 7 nights, 1 apartment
AU$1,003 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Room
Terrace/patio
Dining
Living area
Exceptional
(31 reviews)

Enjoy Gorgeous Sunsets From Your Waterfront Beach House.

Hull

8% off
AU$4,302
for 7 nights, 1 home
AU$615 per night
includes taxes & fees
Enjoy Gorgeous Sunsets From Your Waterfront Beach House.
Exterior detail
Exterior detail
Interior
Living area
Exceptional
(6 reviews)

3-bedroom 2 baths beautiful victorian with WiFi, AC

Boston

8% off
AU$6,524
for 7 nights, 1 apartment
AU$932 per night
includes taxes & fees
3-bedroom 2 baths beautiful victorian with WiFi, AC
Dining
Living area
Living area
Tufts campus is just a 1 minute walk away with beautiful areas for sitting
Exceptional
(11 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

8% off
AU$5,197
for 7 nights, 1 apartment
AU$742 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Room
Interior
Living area
Private kitchen
Exceptional
(48 reviews)

World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train

Boston

9% off
AU$5,608
for 7 nights, 1 apartment
AU$801 per night
includes taxes & fees
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Interior
Living area
Interior
Dining
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
AU$5,837
for 7 nights, 1 apartment
AU$834 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Bedroom 2,
Cool Historic Details in this 1860's townhome apartment,  stairs required!
Dining
Roof top deck with city views!!
Exceptional
(46 reviews)

Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!

Boston

8% off
AU$6,899
for 7 nights, 1 apartment
AU$986 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Private kitchen
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$5,979
for 7 nights, 1 apartment
AU$854 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Private kitchen
Interior
Room
Private kitchen
Exceptional
(25 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,627
for 7 nights, 1 apartment
AU$804 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
  • 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. TD Garden and Fenway Park 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:

  • New England Aquarium (3.7 mi / 6 km)
  • Encore Boston Harbor (4.7 mi / 7.5 km)
  • Harpoon Brewery (3.5 mi / 5.6 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 most popular type of holiday home accommodation in Winthrop?
The most popular types of holiday homes in Winthrop are apartments. Hoping for something different? Stayz offers a variety of options to match our guests' unique needs, so you'll see holiday homes in all sizes and shapes. The perfect fit is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Winthrop?
A range of factors can influence how much you pay for a holiday home in Winthrop, including the season, type of property and length of stay. However, all of our holiday homes have something in common — excellent value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Winthrop?
When you travel and the style and size of the property will influence the cost of your beachside holiday home. Click on your Winthrop travel dates to see all your options on Stayz. Can't live without a private pool? Use the filters to choose the features and amenities you want in your beach house.
Are there pet-friendly holiday homes in Winthrop?
With six holiday homes that welcome four-legged guests, your furry companion can join in on your Winthrop break. Use the filter tool to search our pet-friendly holiday homes and find a pad that'll set tails wagging on Stayz.
What are popular home amenities in Winthrop?
Tennis, nearby museums and a swimming pool are the most popular home amenities in Winthrop. Whether you're taking to the road by yourself, with your significant other or a group of best friends, Stayz will help you find a holiday home that suits your tastes with all the extras you're looking for.
Are there holiday homes in Winthrop that welcome kids?
With six family-friendly holiday properties to choose from in Winthrop, now is the perfect time to introduce the kiddos to the excitement of travel. Simply check our "Properties good for families" filter box to browse stays loaded with amenities ideal for families on the move, such as living rooms, yards, entertainment units and bunk beds.
What are the top attractions for families in Winthrop?
Keep the kids entertained at these fantastic family-friendly attractions in Winthrop:
  • New England Aquarium
  • Museum of Science
  • Revere Beach
Are there one-bedroom holiday homes in Winthrop?
You can pick from three one-bedroom homes in Winthrop. Whether you're on the lookout for a secluded cottage or a cabin, our one-bedroom homes are just right if you don't require loads of space. One of the best parts about having your own digs? You won't have to share your holiday with strangers.
Can I find two-bedroom holiday homes in Winthrop?
Take off with your besties and enjoy a relaxing escape in one of the three two-bedroom holiday properties Winthrop has to offer.
Are there holiday homes with WiFi in Winthrop?
Winthrop has four holiday homes with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to scrolling social media, these Stayz homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Winthrop?
Winthrop has five holiday homes where you can relax and recharge in air-conditioned comfort. To locate a stay on Stayz that provides this perk, enter your desired travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Winthrop?
The minimum required age is usually 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your chosen Winthrop stay before you book.
How long can I rent a holiday home in Winthrop for?
The amount of time you can book a Winthrop holiday home for is up to the property. Simply enter your travel dates to browse available options that offer extended stays. They include all you require to make your extended getaway more comfortable like laundries and air conditioning. Some holiday homes might also offer weekly or monthly discounts, so you can hang around longer for less.

More holiday ideas