Southeast Massachusetts Mountain Vacations 2026

Plan, book, travel with confidence
Better together
Save up to ￥109,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Mountain vacation packages in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Atlas Hotel

Allston

Save 100% on your flight

￥132,905

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.6/10 Exceptional! (77 reviews)

Very clean rooms. House service actually came twice one to clean up and the other to restock - Luisa and Dilicia were very warm and nice. Staff are very hospitable, right from my arrival to departure

Reviewed on May 12, 2026

The Charles Hotel

West Cambridge

Save 100% on your flight

￥174,218

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.4/10 Exceptional! (1,000 reviews)

Excellent location and great staff

Reviewed on May 3, 2026

The Lenox Hotel Boston

Back Bay

Save 100% on your flight

￥196,177

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.6/10 Exceptional! (1,513 reviews)

I love this place !! Everything it’s excellent!! Love it

Reviewed on May 11, 2026

Iris Hotel Boston

Coolidge Corner

Save 100% on your flight

￥171,300

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.4/10 Exceptional! (523 reviews)

Stayed for 2 nights. Very nice hotel, comfortable bed, quiet room, great amenities, friendly and attentive staff. Will definitely stay here again.

Reviewed on May 9, 2026

citizenM Boston Back Bay

Fenway–Kenmore

Save 100% on your flight

￥187,342

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.4/10 Exceptional! (2,635 reviews)

This hotel is one of the best hotels I have ever stayed in, it is extremely clean and organized.

Reviewed on May 11, 2026

Don't see what you're looking for?

See all available trips from Chicago to Southeast Massachusetts

View all trips

5* Mountain vacations in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.

Omni Boston Hotel at the Seaport

Seaport District

￥228,396

per person

Jul 5 - Jul 10

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.2/10 Wonderful! (4,630 reviews)

Nice except the pool was closed during our staff and that was a big reason for picking hotel

Reviewed on May 13, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

￥450,014

per person

Jul 5 - Jul 10

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

clean and great staff

Reviewed on May 8, 2026

Luxury Apartments by Hyatus at Boston Everett

￥449,850

per person

Aug 3 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Boston (BOS)

10/10 Exceptional! (1 review)

Family trip for competition travel and the property was exactly what we needed. Clean room, comfortable beds, and a peaceful environment after long tournament days. Staff was professional and welcoming, and the location made everything easier for our family. Traveling with kids can be stressful, but this stay helped us reset and stay focused. Would definitely stay again.

Reviewed on May 12, 2026

Don't see what you're looking for?

See all available trips from Chicago to Southeast Massachusetts

View all trips