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Deerfield Vacation Packages

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A river winding through a valley with autumn foliage, surrounded by fields and distant hills.

Deerfield
Massachusetts
United States of America
North America
Hotwire.com

Deerfield Flight + Hotel Packages

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

Porter Square Hotel

3 out of 5

Price was $491, price is now $366 per person

$366

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harvard Square and Encore Boston Harbor are located nearby.

Clean and comfortable - I was happy to stay a couple nights at the Porter Square Hotel!

Reviewed on Oct 27, 2026

Boston Lodge and Suites

4 out of 5

Save 100% on your flight

Price was $963, price is now $536 per person

$536

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Boston (BOS)

Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

5 out of 5

Save 100% on your flight

Price was $1,544, price is now $920 per person

$920

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

Excellent as always.

Reviewed on Oct 27, 2026

Raffles Boston

5 out of 5

Save 100% on your flight

Price was $1,863, price is now $1,208 per person

$1,208

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Beautiful place to stay

Reviewed on Oct 27, 2026

Delamar West Hartford

4 out of 5

Save 100% on your flight

Price was $1,137, price is now $790 per person

$790

per person

Jan 21 - Jan 24

found 24 hours ago

Roundtrip flight included

Orlando (MCO) to Hartford (BDL)

Book a stay at this spa hotel in West Hartford. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions PeoplesBank Arena and Blue Back Square are located nearby.

Four Seasons Hotel Boston

5 out of 5

Save 100% on your flight

Price was $1,821, price is now $1,291 per person

$1,291

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Ashworth by the Sea

3 out of 5

Price was $736, price is now $553 per person

$553

per person

Dec 6 - Dec 12

found 20 hours ago

Roundtrip flight included

Raleigh (RDU) to Boston (BOS)

Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Beach and Hampton Beach Casino are located nearby.

Great overnight stay!

Reviewed on Oct 27, 2026

The Langham, Boston

5 out of 5

Price was $1,328, price is now $1,025 per person

$1,025

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.

Excellent experience

Reviewed on Oct 22, 2026