
Massachusetts Pet-friendly Vacations
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Top Pet-friendly vacation packages in Massachusetts
Price found within the past 48 hours. Click for updated prices.

Revere Hotel Boston Common
Bay Village
Save 100% on your flight
Price was ¥182,586, price is now ¥140,758 per person
¥140,758
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,991 reviews)
Expensive, and check to make sure rooftop is open, but really good staff and location
Reviewed on May 12, 2026

The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was ¥189,748, price is now ¥151,944 per person
¥151,944
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (2,315 reviews)
Clean room. Nice staff. Great location.
Reviewed on May 7, 2026

Hotel AKA Boston Common
Downtown Boston
Price was ¥219,018, price is now ¥192,044 per person
¥192,044
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,610 reviews)
Very comfy bed. Room was spacious and nice. It needs a better coffee machine in the room. The Nespresso did not work.
It was inconvenient though to have a fire alarm test right before checking out time! I almost missed my uber ride because the elevator gates were locked and I had to run down six flights of stairs with my luggage. This was 10 am; check out is at 11 am.
Reviewed on May 10, 2026

Kimpton Marlowe Hotel by IHG
East Cambridge
Price was ¥420,868, price is now ¥403,280 per person
¥403,280
per person
Jul 17 - Jul 21
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,000 reviews)
Very nice hotel, great location. Staff were incredible. Would recommend to anyone.
Reviewed on Apr 26, 2026
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View all trips4 Night Pet-friendly vacations in Massachusetts
Price found within the past 48 hours. Click for updated prices.

Revere Hotel Boston Common
Bay Village
Save 100% on your flight
Price was ¥182,586, price is now ¥140,758 per person
¥140,758
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,991 reviews)
Expensive, and check to make sure rooftop is open, but really good staff and location
Reviewed on May 12, 2026

The Colonnade Hotel Back Bay
Back Bay
Save 100% on your flight
Price was ¥189,748, price is now ¥151,944 per person
¥151,944
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (2,315 reviews)
Clean room. Nice staff. Great location.
Reviewed on May 7, 2026

Hotel AKA Boston Common
Downtown Boston
Price was ¥219,018, price is now ¥192,044 per person
¥192,044
per person
Jul 5 - Jul 9
found 6 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,610 reviews)
Very comfy bed. Room was spacious and nice. It needs a better coffee machine in the room. The Nespresso did not work.
It was inconvenient though to have a fire alarm test right before checking out time! I almost missed my uber ride because the elevator gates were locked and I had to run down six flights of stairs with my luggage. This was 10 am; check out is at 11 am.
Reviewed on May 10, 2026
Don't see what you're looking for?
See all available trips from Chicago to Massachusetts
View all tripsTop Pet-friendly Massachusetts Hotels

Kimpton Marlowe Hotel by IHG
25 Edwin H. Land Blvd Cambridge MA
The price is ¥26,792 per night from May 22 to May 23
¥26,792
¥36,547 total
May 22 - May 23
includes taxes & fees
Four-legged friends will enjoy free stays and pet-approved amenities, like food and water bowls, at this city-center hotel. If you need a walk during your visit, ...
9.2/10 Wonderful! (1,001 reviews)
Our stay at the Kimpton Marlowe Hotel was absolutely wonderful. The staff were fantastic from start to finish and truly made us feel welcomed throughout our stay. The amenities were excellent and added to the overall experience. While the bathroom could have used a little TLC, everything was very ...
Reviewed on May 10, 2026

Dune Crest Hotel
535 Route 6 North Truro MA
The price is ¥15,447 per night from May 20 to May 21
¥15,447
¥17,678 total
May 20 - May 21
includes taxes & fees
Stay at this hotel in North Truro. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
The room was very clean the location was exactly where we wanted not in the middle of anything but very close to all the places we wanted to go. The property is a little dated but kinda in a weird way adds to the charm
Reviewed on Dec 30, 2025

Green Harbor Waterfront Lodging
134 Acapesket Road East Falmouth MA
The price is ¥17,966 per night from May 18 to May 19
¥17,966
¥20,563 total
May 18 - May 19
includes taxes & fees
Stay at this hotel in East Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (487 reviews)
Yes to pets. No one was in the office when we checked in but keys were readily available. Waterfront view. Lovely grounds
Reviewed on May 12, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
