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Check prices for these dates

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4 Rab. II - 6 Rab. II
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Compare 606 Vacation Homes in Winthrop with updated reviews, rates, and availability.

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Smart TV, video games, computer monitors, printers

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

9.8 out of 10, Exceptional, (52)
"We were in town for the New Balance Indoor Track Nationals. Our two athletes were able to relax and eat well which gave them a great start for competition. Susan was an amazing host. She provide help when needed, recommendations for pizza and driving directions. The only thing that would be helpful was to know that the king bedroom can only be accessed through another bedroom which was tricky for us staying with non family members.Other than that everything else wes just right."
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Interior

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

9.8 out of 10, Exceptional, (155)
"Nice neighborhood. My only concern was there are a lot of stairs.Great location close to everything, Good restaurants close by. Had a wonderful time. "
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Clean, Contemporary Escape | Near T
TV, offices

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Exterior detail

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

9.0 out of 10, Wonderful, (26)
"I enjoyed my trip to Boston in this VRBO. It's very easy to get ubers in and out of the city which is awesome. As a house cleaner, I just have a couple of observations that I think the host should take into consideration. The hand towel was messed up on the hanger (making it look used by other guests). There was lint (??) in the drain of the kitchen sink. And the fan in the living room 100% needs some attention. I am not a picky person but some people are so I wanted to point those out....
The price is SAR 765
SAR 1,630 total
includes taxes & fees
30 Mar - 31 Mar
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Fridge, microwave, oven, stovetop

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (72)
"Clean and convenient. Loud neighbors"
The price is SAR 371
SAR 1,052 total
includes taxes & fees
16 Apr - 17 Apr
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Interior

Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

10.0 out of 10, Exceptional, (67)
"My family and I had a wonderful stay at Luxury Bayside Jewel in Squantum, MA, over the holidays, and I cannot recommend this property enough. From the start, the property manager, Susan, made the experience seamless. She was incredibly responsive to all my questions before and during the trip, addressing even the smallest details—like when and where to put the trash out—with patience and care.The home itself exceeded all expectations. Thoughtful touches made us feel welcome from the moment we...
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Entire Home 2BR 2BTH Quite Area with parking
Fridge, microwave, oven, stovetop

Entire Home 2BR 2BTH Quite Area with parking

10.0 out of 10, Exceptional, (1)
"The Quiet Single Family House was the perfect place to stay for our group of a mom and 3 college-aged girls. We had plenty of space, the home was very clean and comfortable, and we were central to everything we wanted to do in the area. The neighborhood was peaceful and it wasn’t far to restaurants and grocery stores. The homeowner was a great source of information on things to do in the area as well as very responsive to any questions I had. I’d definitely rent from her again. We had a...
Entire Home 2BR 2BTH Quite Area with parking
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (56)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Incredible Boston Home | Near T
TV, offices

Incredible Boston Home | Near T

Incredible Boston Home | Near T
Belmont Home < 3 Mi to Harvard Square!
Interior

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We were in town for a family gathering nearby, and Joanne’s home was the perfect resting spot for the four of us. The beds were very comfortable, the shower was great, and the kitchen was well stocked with cooking supplies. Joanne was an incredibly thoughtful, kind, and responsive host. We will definitely stay here next time we are in town. Thank you, Joanne!"
The price is SAR 506
SAR 1,011 total
includes taxes & fees
1 Apr - 2 Apr
Belmont Home < 3 Mi to Harvard Square!
Beautiful renovated 3 bedroom apt near Boston.
Fridge, microwave, oven, stovetop

Beautiful renovated 3 bedroom apt near Boston.

9.8 out of 10, Exceptional, (73)
"Very clean and quiet home. Convenient to downtown and great neighborhood. Loved the park across the street for our dog. Beautiful interior. Will definitely stay there again."
Beautiful renovated 3 bedroom apt near Boston.
Enchanting Hidden Door Escape
Fridge, microwave, oven, stovetop

Enchanting Hidden Door Escape

2.0 star property
10.0 out of 10, Exceptional, (11)
"This was a convenient pick for us, being only about 1.5 miles from other family members home. We didn't spend much time there but it was very comfortable. The weather got very cold for a few days, below freezing and we had no hot water upstairs. I contacted management and they had someone out within hours, ON A SUNDAY and started addressing the problem. I would stay here again."
The price is SAR 977
SAR 2,361 total
includes taxes & fees
2 Apr - 3 Apr
Enchanting Hidden Door Escape
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Beach

CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

2.0 star property
9.6 out of 10, Exceptional, (15)
"Beautiful home, spacious, clean, warm, and cozy. Enough space for a family of 5. The neighborhood was easy to find and navigate. The mattresses were not as supportive as we’re used to but we didn’t go to Boston/Chelsea to sleep. The shower was excellent. The owner lives close by which came in handy when the smoke detectors went off on our first night and we couldn’t figure out why. He was prompt in making sure we were safe and the house wasn’t burning and then proceeded to take care of the...
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Leslie's Retreat: Spacious home ideally located to everything
Interior

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (225)
"Home was perfect for our family get together. Location was super close to downtown shops and tours. Plenty of towels and blankets. Lots of hot water for our group of 10. We had 3 vehicles and had a pretty easy time street parking one. Check in email was detailed and helpful. Check out process was simple, for which we were very grateful. Great stay overall!"
Leslie's Retreat: Spacious home ideally located to everything
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Aerial view

Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

9.2 out of 10, Wonderful, (25)
"I reserved the house for 4 days just so my 17 year old daughter and her 3 best friends could spend quality time in Boston on her birthday. We really liked the house; it’s a nice space with all the necessities and very cozy. it was a great fit for our family and we truly enjoyed it. It’s actually minutes to everything in Boston, and we would stay there again if we come back into town. "
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
3 bedrooms, desk, iron/ironing board, WiFi

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.6 out of 10, Exceptional, (4)
"My group with 4 adults and 2 teens was very comfortable in this home. It is in an upscale neighborhood, There is a park directly behind the property and the view is amazing. We would definitely stay here again!"
The price is SAR 863
SAR 2,229 total
includes taxes & fees
6 Apr - 7 Apr
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Charming home with deck- walkable to transit, shops & restaurants
Fridge, microwave, oven, stovetop

Charming home with deck- walkable to transit, shops & restaurants

10.0 out of 10, Exceptional, (1)
"My family and I were in town to tour Boston College because our son starts there in the fall and we wanted to stay near the school and get the feel of the neighborhood. The home was in a perfect location and great neighborhood. We were only a few minutes from the college and about 20 minutes from downtown Boston. The host was great with recommendations to stores and restaurants both near the home and downtown. I would definitely stay here again. Also, I drive a big truck so off street parking...
Charming home with deck- walkable to transit, shops & restaurants
Hidden Gem right in the city of Boston!
Interior

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (17)
"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
The price is SAR 488
SAR 1,466 total
includes taxes & fees
30 Mar - 31 Mar
Hidden Gem right in the city of Boston!
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
TV

Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

10.0 out of 10, Exceptional, (13)
"The home is well cared for and beautiful. The beds were very comfortable. It was the perfect spot for our family getaway, very close to Boston. Would stay here again in a heartbeat if we are ever in the area again!"
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Bright Boston House | near T
Fridge, microwave, oven, stovetop

Bright Boston House | near T

Bright Boston House | near T
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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Other property types in Winthrop

Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (174)
"Very clean and quiet "
The price is SAR 383
SAR 806 total
includes taxes & fees
30 Mar - 31 Mar
Maverick Suites at 28 Fenway
Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (448)
"Great location. Furniture was not that comfortable. A hot plate and larger fridge would be helpful. "
The price is SAR 638
SAR 740 total
includes taxes & fees
22 Apr - 23 Apr
Sonder 907 Main
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (192)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is SAR 446
SAR 719 total
includes taxes & fees
15 Apr - 16 Apr
Temple Place Suites
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.