A coastal town with a lighthouse, sandy beach, and residential buildings.

Winthrop Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winthrop vacation rentals

A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

1. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.0 out of 10, Wonderful, (17 reviews)
"This is a convenient small apartment. However, it should be made clear that it is under the flight path to Logan airport. There were planes flying over till around 23:30, and they started again around 05:30. They were pretty loud."
United Kingdom
Philip
$242 nightly
The price is $270
Oct 13 - Oct 14
Total with taxes and fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A living room with a fireplace, a television, and a dining area with chairs and a table.

2. Casa de Los Clarey • Boston • Logan • Beaches • Free Parking

Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
Winthrop
10.0 out of 10, Exceptional, (58 reviews)
"Loved staying here, great host and great location close to Boston and Salem!"
United States
Stephanie M.
$361 nightly
The price is $403
Oct 7 - Oct 8
Total with taxes and fees
Casa de Los Clarey • Boston • Logan • Beaches • Free Parking
A modern kitchen with wooden cabinets, a refrigerator, and a dining area with chairs.

3. Beautiful 3-bedroom apartment with AC in welcoming Winthrop

Beautiful 3-bedroom apartment with AC in welcoming Winthrop
Winthrop
$389 nightly
The price is $435
Oct 6 - Oct 7
Total with taxes and fees
Beautiful 3-bedroom apartment with AC in welcoming Winthrop
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

4. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (45 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
$313 nightly
The price is $360
Oct 5 - Oct 6
Total with taxes and fees
Bright 2BR by Boston Waterfront
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

5. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.4 out of 10, Good, (26 reviews)
"Cute space! Wasn’t too difficult navigating Boston from this location."
United States
Rebecca
$330 nightly
The price is $380
Oct 5 - Oct 6
Total with taxes and fees
The Concord Hotel
A stone house with a garden bed, a hose, and a brick pathway.

6. Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A hallway with brick walls and a polished floor, leading to a door.

7. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (28 reviews)
"NICE PLACE TO USE AS A BASE TO SEE TO TRAVEL FROM"
United States
Rodney S.
$187 nightly
The price is $205
Oct 29 - Oct 30
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
A waterfront cityscape with a prominent clock tower, a river with boats, and modern buildings.

8. Location+Comfort+Convenience

Location+Comfort+Convenience
East Boston
9.4 out of 10, Exceptional, (88 reviews)
"Fantastic location, easy access to Maverick station! Cozy space. Convenient to restaurants and the mattresses are excellent!"
United States
Elaine S.
$305 nightly
The price is $351
Oct 21 - Oct 22
Total with taxes and fees
Location+Comfort+Convenience
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

9. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (329 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$316 nightly
The price is $353
Oct 18 - Oct 19
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A compact kitchen with white cabinets, a black countertop, and two wooden chairs.

10. Modern 2 BR, 1BA Near Convention Center & Seaport

Modern 2 BR, 1BA Near Convention Center & Seaport
South Boston
9.8 out of 10, Exceptional, (242 reviews)
"Very clean apartment, in great location with friendly host."
United States
Sylwia G.
$372 nightly
The price is $428
Oct 4 - Oct 5
Total with taxes and fees
Modern 2 BR, 1BA Near Convention Center & Seaport
A building with a sign reading "GREEN TURTLE" and a dock with red chairs.

11. Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.

Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
Charlestown
10.0 out of 10, Exceptional, (258 reviews)
"Loved this experience!!! Would book this again! So convenient to see Boston! "
United States
Ellen Z.
$425 nightly
The price is $488
Oct 7 - Oct 8
Total with taxes and fees
Romantic Boston Harbor Houseboat Stay for 2 people. A/C. Close to Freedom Trail.
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

12. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (74 reviews)
"Great location and the host was very helpful for everything. Definitely I’m gonna stay here again."
United States
Sandy M.
$419 nightly
The price is $482
Oct 7 - Oct 8
Total with taxes and fees
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
A modern kitchen with white cabinets, stainless steel appliances, and a glass dining table set for six.

13. 3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (20 reviews)
"Wonderful place and close to everything!"
United States
Erin A.
3BR3Bth Entire House/Steps to Downtown & TD Garden
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

14. 3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
East Somerville
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$409 nightly
The price is $457
Oct 4 - Oct 5
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
An outdoor patio area with a covered seating area, a fire pit, and a well-lit ambiance.

15. 🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (93 reviews)
"Honestly, the Boiler Room is even bigger than it looks in the pictures and is so perfectly curated! We LOVED our stay and if I ever get the opportunity to come back to Boaton, I will be staying here!"
United States
Katie C.
$311 nightly
The price is $358
Oct 5 - Oct 6
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
A residential house with a covered porch, a garage, and a well-maintained garden.

16. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (15 reviews)
"Will not be disappointed!"
United States
Dave O.
$263 nightly
The price is $294
Nov 1 - Nov 2
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A modern kitchen with stainless steel appliances, a blue and white patterned sofa, and a cityscape painting on the wall.

17. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (18 reviews)
"Great location- excellent place!"
United States
Deborah S.
$369 nightly
The price is $424
Oct 4 - Oct 5
Total with taxes and fees
Perfetto North End 1brm
A marina with numerous boats docked, a large building with a green roof, and a cityscape in the background.

18. Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
Boston
10.0 out of 10, Exceptional, (136 reviews)
"I reserved the Green Turtle for out-of-town guests over Memorial Day weekend and will do so again. They will thrilled to stay on the water their first time visiting Boston and found the boat comfortable and restful."
United States
Gale P.
$586 nightly
The price is $673
Oct 8 - Oct 9
Total with taxes and fees
Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat
A modern kitchen with white cabinets, a grey tiled backsplash, a microwave, a kettle, and two stools.

19. 14a-Cozy and well decorated apartment in awesome Boston

14a-Cozy and well decorated apartment in awesome Boston
Dorchester
10.0 out of 10, Exceptional, (34 reviews)
"The whole place is excellent, location and services just around the corner "
United States
Ramon G.
$464 nightly
The price is $533
Oct 4 - Oct 5
Total with taxes and fees
14a-Cozy and well decorated apartment in awesome Boston
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

20. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (17 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
$224 nightly
The price is $263
Oct 20 - Oct 21
Total with taxes and fees
Stunning Back Bay Studio Apartment
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winthrop Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Nautical theme"
Michael Howard 2-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winthrop

Everything you need to know about Winthrop vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winthrop vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winthrop vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winthrop vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winthrop. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winthrop in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $170 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winthrop rentals

At Expedia, we put the best Winthrop vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winthrop rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winthrop vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winthrop. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals near top points of interest in Winthrop, or you can choose a more secluded option if you're looking for relaxation. Visitors to Winthrop speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the cafes and waterfront during your trip.

What are some of the best vacation home rentals in Winthrop?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation home rental near Winthrop offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals are there in Winthrop?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Winthrop stay.

What can I see and do in Winthrop?

Winthrop Beach and Donovan Beach are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include Fenway Park and Faneuil Hall Marketplace.

What are vacation rentals like in Winthrop?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Winthrop. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.