Winthrop Trip
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Top Winthrop Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was ₹109,717, price is now ₹73,867 per person
₹73,867
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Great gym and staff. Kudos to Nicky at the front desk.
Reviewed on 22 Feb 2026
Boston Harbor Hotel
North End
Price was ₹238,390, price is now ₹125,647 per person
₹125,647
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.
Reviewed on 25 Jan 2026
Eurostars The Boxer
West End
Save 100% on your flight
Price was ₹120,790, price is now ₹77,570 per person
₹77,570
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
I had a pleasant stay there. The receptionists are so nice and helpful. I came early before the checking time but they let me in. Extending reservation was also easy and they're helpful. They let me come back in after my buses were cancelled, and that's a very great service. They provided good amenities too. So far, it's been a comfortable stay in the hotel; and the location is quite near with the north station and stores if you need to buy meals just in case.
Reviewed on 24 Feb 2026
Raffles Boston
Back Bay
Save 100% on your flight
Price was ₹230,063, price is now ₹149,497 per person
₹149,497
per person
30 Mar - 4 Apr
found 1 day ago
Return flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!
Reviewed on 24 Feb 2026
Top hotels in Winthrop
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹12,197 per night from 1 Mar to 2 Mar
₹12,197
₹17,306 total
1 Mar - 2 Mar
includes taxes & fees
9.6/10 Exceptional! (4,044 reviews)
Very helpful and kind staff. Clean rooms and comfy beds. Will stay again!
Reviewed on 25 Feb 2026
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹9,216 per night from 1 Mar to 2 Mar
₹9,216
₹14,440 total
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (4,503 reviews)
Good people and nice service
Reviewed on 26 Feb 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is ₹11,113 per night from 8 Mar to 9 Mar
₹11,113
₹16,648 total
8 Mar - 9 Mar
includes taxes & fees
8.4/10 Very Good! (3,101 reviews)
Very attentive and friendly staff , clean rooms . Our stay was very pleasant
Reviewed on 25 Feb 2026
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.
Popular places to visit
Fenway Park
4.5/5(61 reviews)
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Gillette Stadium
3/5(2 reviews)
Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theatre scene and great live music.
Boston Common
4.5/5(204 reviews)
The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
