Package deals near Kenmore Square

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Top Kenmore Square vacation deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Dorchester
8.4/10 Very Good! (190 reviews)

Oct 19 - Oct 23

4 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Non-stop • Coach
Price was $1,542, price is now $714 per person
$714
per person
found 13 hours ago
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

North End
9.8/10 Exceptional! (1,006 reviews)

Oct 30 - Nov 2

3 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,677, price is now $931 per person
$931
per person
found 1 day ago
The rooms were impeccable, and the staff was excellent. They were very proactive and helpful in resolving a few challenges we experienced during our trip. The overall experience and the attention given to toddlers and children were amazing. It is also worth mentioning that even the crib was excellent, which made our stay much more comfortable. We truly appreciated the level of service and attention to detail.

Reviewed on Aug 5, 2026

Iris Hotel Boston
4.0-star property

Iris Hotel Boston

Coolidge Corner
9.4/10 Exceptional! (612 reviews)

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,435, price is now $1,447 per person
$1,447
per person
found 13 hours ago
Hotel très propre et confortable. Personnel acccueillant. Seul le stationnement est un peu dispendieux

Reviewed on Aug 5, 2026

The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

9.2/10 Wonderful! (268 reviews)

Oct 15 - Oct 20

5 night stay

Dallas (DFW) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,316, price is now $849 per person
$849
per person
found 1 day ago
P Indoor pool and hot tub loved and the outdoor Shack was great

Reviewed on Jun 8, 2026

Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

Coolidge Corner
6.8/10 (5 reviews)

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,689, price is now $1,759 per person
$1,759
per person
found 1 day ago
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.

Reviewed on Jul 6, 2026

Chatham Tides
2.5-star property

Chatham Tides

9.4/10 Exceptional! (735 reviews)

Oct 15 - Oct 20

5 night stay

Dallas (DFW) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,413, price is now $960 per person
$960
per person
found 1 day ago
I had a wonderful stay at Chatham Tides from Sunday to Monday and can't recommend it highly enough! From the moment I arrived, the staff made me feel so welcome. Everyone was incredibly kind, helpful, and accommodating. A special thank you to Russell and MaryEllen for their outstanding hospitality—they truly made my stay memorable. My room was sparkling clean, comfortable, and had the most idyllic oceanfront location. Waking up to the sound and view of the ocean was absolutely perfect. Monday turned out to be a gorgeous beach day, and the manager very generously offered me a late checkout so I could enjoy a few extra hours by the water. That thoughtful gesture really exemplified the exceptional level of customer service at Chatham Tides. The only suggestions I'd offer are providing a little more guidance on where guests can find bottled water, and perhaps adding a late-night snack or vending option for those midnight cravings. Neither took away from what was an excellent experience. Overall, this was a lovely stay with exceptional hospitality in a beautiful setting. Five stars—I can't wait to come back!

Reviewed on Aug 5, 2026

Hotel deals near Kenmore Square

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Free Cancellation
Reserve now, pay when you stay
0.57 mi from Kenmore Square
The price is $221 total per night
$221 total
per night
Sep 6 - Sep 7
Hyatt Regency Boston/Cambridge features a 24-hour gym, free WiFi in public areas, and conference space. Valet parking is available for USD 58.00 per night. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Free Cancellation
Reserve now, pay when you stay
0.76 mi from Kenmore Square
The price is $199 total per night
$199 total
per night
Aug 16 - Aug 17
Guests staying at The Midtown Hotel MOD Collection by Sonesta enjoy a gym, free WiFi in public areas, and a fireplace in the lobby. Self parking is available for USD 45 per night. The 24-hour front desk has multilingual staff ready to assist with luggage storage and securing valuables. This smoke-free hotel also has an ATM.
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Free Cancellation
Reserve now, pay when you stay
0.4 mi from Kenmore Square
The price is $167 total per night
$167 total
per night
Aug 16 - Aug 17
CitizenM Boston Back Bay features a 24-hour gym, free WiFi in public areas, and coffee in a common area. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include a microwave in a common area, express check-in, and express check-out.
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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.

Book a Kenmore Square vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Kenmore Square, now is the perfect time. Book your getaway to Boston with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing Boston sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Kenmore Square, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Kenmore Square vacation. Book your Boston package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Kenmore Square any longer. Save a bundle and book your Boston escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.