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Our top choices for Winthrop condo rentals

Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
2.0 star property
Marblehead
10.0 out of 10, Exceptional, (2)
"This place is awesome. First time going to the east and I’d rather stay here over any 5 star hotel. Janie is so nice n gave some great suggestions for bars/places to eat while there. The only bad part about the trip was having to go home. Easy parking, fairy tale like back yard area, historic house, and only a 4 minute walk to the ocean. "
United States
Madison J.
The price is AED 273
AED 748 total
includes taxes & fees
4 Jan - 5 January 2026
Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Beacon Hill
The price is AED 375
AED 1,026 total
includes taxes & fees
11 Jan - 12 January 2026
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead
10.0 out of 10, Exceptional, (71)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
The price is AED 239
AED 809 total
includes taxes & fees
31 Dec - 1 January 2026
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail
Downtown Boston
10.0 out of 10, Exceptional, (52)
"Spacious condo, perfect location, and exceptional hospitality from mangers."
United States
Robert S.
The price is AED 575
AED 1,282 total
includes taxes & fees
22 Jan - 23 January 2026
Bright & Spacious Loft Steps to the Freedom Trail

*NEW Spacious 3BR |Downtown|Salem+Beverly|Parking

*NEW Spacious 3BR |Downtown|Salem+Beverly|Parking
Beverly
10.0 out of 10, Exceptional, (21)
"Very clean property, responsive hosts, great area, close to Salem! We had a great time and loved it. The beds were very comfortable! "
United States
Jaclyn K.
The price is AED 768
AED 1,662 total
includes taxes & fees
2 Jan - 3 January 2026
*NEW Spacious 3BR |Downtown|Salem+Beverly|Parking

Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
2.0 star property
Wakefield
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Alex c.
The price is AED 512
AED 1,463 total
includes taxes & fees
5 Jan - 6 January 2026
Stylish home next to train to Boston, near Salem

Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom
Salem
10.0 out of 10, Exceptional, (58)
"This was a truly wonderful property - clean, generously stocked, perfect location and attentive owner"
United States
Valerie G.
The price is AED 444
AED 1,264 total
includes taxes & fees
6 Jan - 7 January 2026
Downtown Salem - Park & Play Modern 3 Bedroom

*1710 Historic 2BR |Downtown Salem Retreat|Parking

*1710 Historic 2BR |Downtown Salem Retreat|Parking
Downtown Salem
10.0 out of 10, Exceptional, (63)
"We had a fantastic time here! The home was so charming and comfortable, and we loved the decor. The location couldn’t be more perfect (we were able to walk to all the sights we wanted to see in Salem), and the hosts are also very communicative. It truly exceeded our expectations. "
United States
Kristin B.
The price is AED 518
AED 1,230 total
includes taxes & fees
4 Jan - 5 January 2026
*1710 Historic 2BR |Downtown Salem Retreat|Parking

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
9.0 out of 10, Wonderful, (10)
"We enjoyed our stay and would definitely stay here again. It was clean, cute, very cute area, safe, and very short drive to Boston. We really loved the area and the people we interacted with were all so friendly! The beds were very comfy too!!"
United States
Meghan D.
The price is AED 767
AED 1,802 total
includes taxes & fees
24 Jan - 25 January 2026
Modern Three Bedroom Condo - Near Boston

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
10.0 out of 10, Exceptional, (1)
"Very happy with our stay here! The place was clean, warm, and comfortable. I really appreciated the easy check in/out procedures. I loved that we weren’t expected to complete a long list of cleaning tasks before checking out. Crib, pack n play, and high chair were available which is awesome for traveling with a baby. "
United States
Amna S.
The price is AED 694
AED 1,543 total
includes taxes & fees
1 Jan - 2 January 2026
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
2.0 star property
Swampscott
8.4 out of 10, Very Good, (6)
"Beautiful house & views,"
United States
Suzanne P.
The price is AED 802
AED 2,253 total
includes taxes & fees
31 Dec - 1 January 2026
Coastal Charm: Lobster Châto

Modern 2-bedroom condo 1 mile to Salem

Modern 2-bedroom condo 1 mile to Salem
2.0 star property
Beverly
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay!! Excellent location with many walking distance food options. Super clean and super cozy!! Hosts were responsive and caring for our comfort while we stayed. Thank you for the snacks!!! We would definitely stay here again!!!"
United States
Melissa G.
The price is AED 1,010
AED 1,456 total
includes taxes & fees
31 Dec - 1 January 2026
Modern 2-bedroom condo 1 mile to Salem

Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (5)
"Very nice and quiet neighborhood. Would love to rent again if the opportunity presents itself. "
United States
Bobby B.
The price is AED 555
AED 1,436 total
includes taxes & fees
1 Jan - 2 January 2026
Modern & Stylish 1-Bedroom Condo near Downtown

Spacious 3BR Salem Getaway, Modern & Walkable

Spacious 3BR Salem Getaway, Modern & Walkable
Salem
10.0 out of 10, Exceptional, (7)
"We had a great time, all was good. If you get takeout, you may want to make sure you grab salt, pepper, or ketchup packets. Overall we all really enjoyed the accommodations and being a short drive to all the fun sites in Salem."
United States
Tina G.
The price is AED 516
AED 1,130 total
includes taxes & fees
11 Jan - 12 January 2026
Spacious 3BR Salem Getaway, Modern & Walkable

Lg suite for up to 8 ppl/2 floor

Lg suite for up to 8 ppl/2 floor
Dorchester
10.0 out of 10, Exceptional, (12)
"It was a perfect location for our daily plans. The owner was very responsive to our needs "
United States
Mary P.
The price is AED 533
AED 1,756 total
includes taxes & fees
7 Jan - 8 January 2026
Lg suite for up to 8 ppl/2 floor

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Everett
10.0 out of 10, Exceptional, (30)
"Great location! Host was very attentive. Enjoyed our stay."
United States
Kim H.
The price is AED 675
AED 1,586 total
includes taxes & fees
14 Jan - 15 January 2026
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Eastie Gem: Taste of local life by the waterfront, airport and train

Eastie Gem: Taste of local life by the waterfront, airport and train
2.0 star property
East Boston
The price is AED 743
AED 1,606 total
includes taxes & fees
8 Jan - 9 January 2026
Eastie Gem: Taste of local life by the waterfront, airport and train

🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (53)
"Great house, perfect for our family of 5. Pretty far from Boston and weekend train service was spotty so spent quite a bit on Uber but other than that, a fantastic stay!"
United States
Alex S.
The price is AED 915
AED 1,904 total
includes taxes & fees
16 Jan - 17 January 2026
🎖The Ashmont Suite - Close to Subway + Downtown🎖

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston
South Boston
7.8 out of 10, Good, (6)
"Very clean "
United States
Paul A.
The price is AED 698
AED 1,664 total
includes taxes & fees
4 Jan - 5 January 2026
Lovely Two Bedroom Condo in South Boston

Brookline Village, Central Air, 2B, Near Longwood

Brookline Village, Central Air, 2B, Near Longwood
Brookline
9.6 out of 10, Exceptional, (63)
"Very clean, good location, good for 2 couples or family. Loved the provided coffee and snacks."
United States
marvin g.
The price is AED 671
AED 1,549 total
includes taxes & fees
4 Jan - 5 January 2026
Brookline Village, Central Air, 2B, Near Longwood
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

Frequently asked questions

How much do condos in Winthrop cost?
Condos in Winthrop range from AED 809 to AED 2,253 per night. This means plenty of room for your whole family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winthrop?
Choose from 179 condos in Winthrop. No matter if you're taking a trip with the family or organizing a weekend break with your besties, Expedia can help you find the ideal base for your crew.
Why book your condo in Winthrop with Expedia?
Vacationing should be a piece of cake, so if you're on the lookout for condos at an affordable rate, Expedia has got you covered. Save those pennies and pick something small and affordable, or splurge on 5-star accommodations and treat your loved ones. Use our convenient search filters to find a place in Winthrop that suits you best.
How can I find cheap condos in Winthrop?
Expedia can help you locate cheap condos in Winthrop. To lock in your special stay in just a few clicks, simply use the filter tool to refine your search by budget, star rating and amenities.