Highland Trip
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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)
Room was small-but very clean & bright. Beds were very comfortable. SO close to TD garden. Staff was kind & helpful. Breakfast was good. Their parking option was ramp garage that is only 6’2” and not a lot of parking spots for a random Wednesday. If that’s a concern, you may want to look elsewhere. Will absolutely stay again
Reviewed on 26 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
Where to stay in Highland
Find the best Highland areas and neighborhoods for the activities you enjoy most. Learn more about Highland
Willard Beach
2 out of top 10 points of interest in this area
When in Willard Beach, you can plan a visit to Willard Beach and Spring Point Ledge Lighthouse, some noteworthy sights in the nearby area.
Top hotels in Highland
Best Western Merry Manor Inn
700 Main St South Portland ME
Fully refundableReserve now, pay when you stay
The price is ₹8,367 per night from 2 Mar to 3 Mar
₹8,367
₹9,120 total
2 Mar - 3 Mar
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
Pool was fun!
Reviewed on 24 Feb 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is ₹8,913 per night from 29 Mar to 30 Mar
₹8,913
₹9,862 total
29 Mar - 30 Mar
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Location, clean rooms, pleasant staff
Reviewed on 23 Feb 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is ₹7,008 per night from 5 Mar to 6 Mar
₹7,008
₹7,753 total
5 Mar - 6 Mar
includes taxes & fees
8/10 Very Good! (1,378 reviews)
The room was very clean, and the staff was very friendly. The only thing that was disappointing was that when we got ready, and went to use the hot tub it was cold.
Reviewed on 26 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
Maine Military Museum
You can spend an afternoon studying the exhibits at Maine Military Museum during your travels in South Portland. Experience the area's great live music and acclaimed theatre scene.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.