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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.
$144 nightly
The price is $161
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$243 nightly
The price is $279
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
Beverly
10.0 out of 10, Exceptional, (32)
"The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. "
United States
Lawrence D.
$262 nightly
The price is $293
Dec 29 - Dec 30
Total with taxes and fees
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

♥ 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.
$230 nightly
The price is $256
Dec 29 - Dec 30
Total with taxes and fees
♥ 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.
$319 nightly
The price is $367
Jan 22 - Jan 23, 2026
Total with taxes and fees
Bright & Spacious Loft Steps to the Freedom Trail

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)
"we were in Massachusetts for our youngest granddaughters college graduation. This place was great. Good location and great hosts! Beautiful neighborhood Easy to walk to breakfast, lunch or dinner. "
United States
Rebecca Z.
$345 nightly
The price is $385
Jan 25 - Jan 26, 2026
Total with taxes and fees
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.
$319 nightly
The price is $356
Jan 6 - Jan 7, 2026
Total with taxes and fees
Downtown Salem - Park & Play Modern 3 Bedroom

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.
$355 nightly
The price is $397
Dec 27 - Dec 28
Total with taxes and fees
Modern 2-bedroom condo 1 mile to Salem

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.
$572 nightly
The price is $613
Dec 29 - Dec 30
Total with taxes and fees
Coastal Charm: Lobster Châto

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.
$340 nightly
The price is $391
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern & Stylish 1-Bedroom Condo near Downtown

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.
$412 nightly
The price is $474
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lg suite for up to 8 ppl/2 floor

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.
$381 nightly
The price is $426
Dec 28 - Dec 29
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

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.
$295 nightly
The price is $329
Jan 8 - Jan 9, 2026
Total with taxes and fees
Spacious 3BR Salem Getaway, Modern & Walkable

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.
$383 nightly
The price is $428
Jan 12 - Jan 13, 2026
Total with taxes and fees
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

🎖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.
$450 nightly
The price is $517
Jan 16 - Jan 17, 2026
Total with taxes and fees
🎖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.
$420 nightly
The price is $453
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely Two Bedroom Condo in South Boston

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
$380 nightly
The price is $437
Dec 29 - Dec 30
Total with taxes and fees
Eastie Gem: Taste of local life by the waterfront, airport and train

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.
$402 nightly
The price is $416
Jan 4 - Jan 5, 2026
Total with taxes and fees
Brookline Village, Central Air, 2B, Near Longwood

Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach

Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach
Revere
9.6 out of 10, Exceptional, (5)
"Very nice house … read the check in instructions before you get there. "
United States
Morgan R.
$547 nightly
The price is $611
Jan 6 - Jan 7, 2026
Total with taxes and fees
Designer Oceanfront Retreat Featured in Architectural Digest ☀ Steps from Beach

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

*NEW Spacious 3BR |Downtown|Salem+Beverly|Parking
Beverly
10.0 out of 10, Exceptional, (21)
"A very nice stay everything is in walking distance. Food very good "
United States
Deanna F.
$386 nightly
The price is $431
Dec 30 - Dec 31
Total with taxes and fees
*NEW Spacious 3BR |Downtown|Salem+Beverly|Parking
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

Find out more about Winthrop

Winthrop Condo Rentals information

Number of reviews
350
Accommodation
172 Condo Rentals
Lowest Price
$256
Highest Price
$613

Frequently asked questions

How much do condos in Winthrop cost?
Condos in Winthrop range from $256 to $613 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 172 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.
What is there to do in Winthrop near my condo?
The ideal travel accessory is a well-planned schedule. Winthrop Beach is a wonderful place to begin your exploration of Winthrop.

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