Eastern Massachusetts Vacation Packages

Book a Stay + Flight or Car to save on your trip

Top Eastern Massachusetts vacation package deals

Price found within the past 48 hours. Click for updated prices.
Sally Webster Inn
3.0-star property

Sally Webster Inn

9.4/10 Exceptional! (130 reviews)

May 22 - May 25

3 night stay

Miami (MIA) to Boston (BOS)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $746, price is now $555 per person
$555
per person
found 1 day ago
Staying at the Sally Webster Inn was a different experience as we never met the owners, managers or any staff member. The Inn was very clean and comfortable and convenient to Rockport harbor. Breakfast choices were adequate but would have preferred to eat outside of our room. Bathroom was tiny! Bed was comfortable and room was nicely decorated.

Reviewed on Oct 14, 2023

The Franklin Hotel Martha's Vineyard
2.0-star property

The Franklin Hotel Martha's Vineyard

9.2/10 Wonderful! (179 reviews)

May 29 - Jun 1

3 night stay

Miami (MIA) to Vineyard Haven (MVY)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $919, price is now $680 per person
$680
per person
found 1 day ago
Beautiful property in the scenic Edgartown. Very attentive staff. On-site parking was great and conveniently located in walkable distance to the ceter of town and the local Stop n Shop.

Reviewed on Jun 7, 2025

Sea Crest Beach Resort
3.5-star property

Sea Crest Beach Resort

8/10 Very Good! (253 reviews)

Jun 12 - Jun 15

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop • Coach

Boston (BOS) to Orlando (MCO)

JetBlue Airways • Non-stop • Coach
Price was $946, price is now $716 per person
$716
per person
just found
5pm check in- ridiculous 18$ pool cocktails-ridiculous Dirty beaches- extremely ridiculous Mold in bathroom 25$ per night super uncomfortable rollaway bed- ridiculous

Reviewed on Aug 9, 2025

The Westin Waltham-Boston
4.0-star property

The Westin Waltham-Boston

8.8/10 Excellent! (1,095 reviews)

Jun 11 - Jun 15

4 night stay

Orlando (MCO) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,335, price is now $1,016 per person
$1,016
per person
found 1 day ago
Beautiful suite with comfy bed! Lovely property with friendly staff. Would definitely stay here again!

Reviewed on Oct 23, 2025

Hotel 1620 Plymouth Harbor
3.0-star property

Hotel 1620 Plymouth Harbor

Plymouth Downtown Waterfront District
8.2/10 Very Good! (1,005 reviews)

May 22 - May 25

3 night stay

Miami (MIA) to Boston (BOS)

Frontier Airlines • Non-stop roundtrip • Coach
Price was $737, price is now $563 per person
$563
per person
found 1 day ago
Staff very friendly

Reviewed on Oct 3, 2025

Top rated hotels for your Eastern Massachusetts vacation package

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Free Cancellation
Reserve now, pay when you stay
28.17 mi from city center
$189 nightly
The price is $220 total per night
$220 total
Apr 5 - Apr 6
Total with taxes and fees
At Omni Boston Hotel at the Seaport, guests enjoy a full-service spa, an outdoor pool, and a 24-hour gym. Valet parking is offered for USD 65 per night. The front desk is staffed 24/7 to help with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include free WiFi in public areas, a hot tub, and a business center.
Pool
Hot Tub
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Free Cancellation
Reserve now, pay when you stay
29.18 mi from city center
$190 nightly
The price is $221 total per night
$221 total
Apr 6 - Apr 7
Total with taxes and fees
Guests of Hilton Boston Park Plaza enjoy a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 70 per day. The front desk has multilingual staff on hand 24/7 to help with luggage storage, tours or tickets, and dry cleaning/laundry. Other amenities at this luxury hotel include conference space, a 24-hour business center, and a computer station.
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Free Cancellation
Reserve now, pay when you stay
28.24 mi from city center
$157 nightly
The price is $182 total per night
$182 total
Apr 5 - Apr 6
Total with taxes and fees
Guests of Seaport Hotel Boston have access to an indoor pool, a gym, and a steam room. Valet parking is available for USD 59 per night. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include free WiFi in public areas, meeting rooms, and a conference center.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in Eastern Massachusetts
View all properties
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.
All Inclusive Vacations
All Inclusive Vacations
Family Vacation Packages
Family Vacation Packages
Adventure Vacation Packages
Adventure Vacation Packages

Explore More Ways to Travel with Travelocity