$217+ Cheap flights from Massachusetts to Road Town (EIS)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EIS
Feb 26 — Mar 51
1 adult, Economy
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Cheapest flights from Massachusetts to Road TownExplore the most affordable flight options available from Massachusetts to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
Explore the most affordable flight options available from Massachusetts to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:18 pm
BOS
- EIS
1 stop18h 37m
Multiple Airlines
Sat 2/78:55 am
EIS
- BOS
1 stop6h 17m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:18 pm
BOS
- EIS
1 stop18h 37m
Multiple Airlines
Sun 2/84:00 pm
EIS
- BOS
1 stop23h 12m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/13:23 pm
BOS
- EIS
1 stop19h 32m
Multiple Airlines
Tue 4/74:00 pm
EIS
- BOS
2 stops45h 55m
Multiple Airlines
Deal found 1/24![Multiple Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/243:23 pm
BOS
- EIS
1 stop19h 32m
Multiple Airlines
Tue 3/314:00 pm
EIS
- BOS
2 stops24h 44m
Multiple Airlines
Deal found 1/24![Multiple Airlines logo]()
$497
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/303:18 pm
BOS
- EIS
1 stop26h 02m
Multiple Airlines
Sat 2/78:55 am
EIS
- BOS
1 stop6h 17m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/224:22 pm
BOS
- EIS
2 stops20h 48m
Multiple Airlines
Sun 3/14:00 pm
EIS
- BOS
1 stop23h 43m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:44 pm
ORH
- EIS
2 stops21h 08m
American Airlines
Wed 3/1811:32 am
EIS
- ORH
2 stops25h 47m
American Airlines
Deal found 1/24![American Airlines logo]()
$870
Find flight deals from Massachusetts to Road Town
Keep the following information in mind while searching for Massachusetts to Road Town flight deals. Data was last updated January 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $488 (Kiwi.com) |
One-way from | $217 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $1,183 |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Road Town that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
Use the filters below to find and compare flights from Massachusetts to Road Town that are best for you.
Fly from
Massachusetts
Fly to
Road Town
Route
Depart
Return
Price
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Tue 3/24
3:23 pm-10:55 am
1 stop19h 32m
Road Town Beef Island
Tue 3/31
4:00 pm-4:44 pm
2 stops24h 44m
$497
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Sun 2/22
3:00 pm-2:10 pm
1 stop22h 10m
Road Town Beef Island
Sun 3/1
4:00 pm-2:43 pm
1 stop23h 43m
$578
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Thu 5/21
10:20 pm-3:35 pm
1 stop17h 15m
Road Town Beef Island
Fri 5/29
11:35 am-4:58 pm
2 stops29h 23m
$691
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Wed 4/29
5:00 am-4:14 pm
1 stop11h 14m
Road Town Beef Island
Mon 5/4
9:00 am-11:07 pm
1 stop14h 07m
$715
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Sun 4/19
6:00 am-2:05 pm
2 stops32h 05m
Road Town Beef Island
Sat 4/25
11:35 am-8:00 am
1 stop20h 25m
$762
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Thu 2/26
5:27 am-7:35 pm
2 stops13h 08m
Road Town Beef Island
Mon 3/2
4:00 pm-11:59 pm
3 stops32h 59m
$787
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Tue 5/19
9:20 am-6:30 pm
2 stops33h 10m
Road Town Beef Island
Fri 5/29
8:00 am-8:44 am
2 stops24h 44m
$797
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Thu 3/12
7:55 am-11:10 am
1 stop27h 15m
Road Town Beef Island
Thu 3/19
7:55 pm-6:00 pm
1 stop22h 05m
$803
WorcesterRoad Town
ORH - EIS
ORHEIS
Worcester
Wed 3/11
1:44 pm-10:52 am
2 stops21h 08m
Road Town Beef Island
Wed 3/18
11:32 am-1:19 pm
2 stops25h 47m
$870
BostonRoad Town
BOS - EIS
BOSEIS
Boston Logan Intl
Tue 4/7
11:18 am-6:10 pm
1 stop6h 52m
$217
Showing 1-10 of 13 results
Best time to book a flight from Massachusetts to Road Town
Have a flexible travel schedule? Discover the best time to fly to Road Town from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Road Town
What is the cheapest month to book a flight from Massachusetts to Road Town?
Currently, June is the cheapest month in which you can book a flight from Massachusetts to Road Town (average of $617). Flying from Massachusetts to Road Town in September is currently the most expensive (average of $727). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Massachusetts to Road Town?
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Road Town. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to Road Town
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Massachusetts to Road Town
Discover the top 2 airlines that operate flights from Massachusetts to Road Town. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$641 | Average$841 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$718 | Average$1,084 | FlexibilityNo cancel fee | On-time71% |