Car Rental - Halifax to Boston?

It's just not possible to pick up in Canada and drop of in US. You'll need a plan B.

2 different countries.

Need to leave the car in Canada.

Why not fly to Boston?

I agree with Claudia, you'll probably have to take a quick flight from Halifax to Boston.

Evidently you are trying to meander down the coast seeing the sites ( and there are many ) on the way . My best guess with a rental would be - pick up the car in Halifax , and drive as far as St Johns ( this assumes that you could pick up and drop at those two points _ You would then be likely to pick up a second rental around Bar Harbor , ME for the rest of your trip . The obvious sticking point is the leg between St Johns and Bar Harbor , if there is a way to connect those two points . ( There is a Hertz agency at the Bar Harbor airport )

I did a bit more looking - this would work - There are Enterprise car rentals in both Halifax and Yarmouth NS you could pick up the car in Halifax , and drop it in Yarmouth NS . Ferry from there to Bar Harbor , and pick up a rental there , drive through Maine down to Boston https://www.ferries.ca/thecat/overview/ and a maphttps://www.google.com/maps/dir/Enterprise+Rent-A-Car,+2000+Barrington+St,+Halifax,+NS+B3J+3K1,+Canada/Enterprise+Rent-A-Car,+Starrs+Road,+Yarmouth,+NS,+Canada/@44.6180655,-68.4042171,7.75z/data=!4m14!4m13!1m5!1m1!1s0x4b5a238bbea6bd89:0xbf44f5e5590ec2db!2m2!1d-63.5772922!2d44.6510092!1m5!1m1!1s0x4b56110ce03eca05:0xc38501647798707!2m2!1d-66.0932015!2d43.8386499!3e0 I think this is a protracted road trip , looking at your dates

Here is our current itinerary (lodging reserved and flights booked into Halifax and out of Boston):

I appreciate all of the feedback you have provided! I had initially thought we would encounter this very issue based on our experience in Italy/Croatia last year, but was assured by our Airbnb host in Halifax that it wouldn't be a problem and related they had relatives that did a one-way trip from NS to Florida... it must have been pre-covid!

In response to the question about our plans:
Arrive in Halifax @ 6:30 a.m. on 9/7 leaving 9/10
Arrive in Baddeck NS on 910 leaving 912
Arrive in Cheticamp on 9/12 leaving 9/14
Arrive in Charlottetown on 9/14 leaving 9/16
Arrive Hopewell Cape 9/16 leaving 9/18
Arrive Saint Andrews NB 9/18 leaving 9/20
Arrive Bar Harbor ME 9/20 leaving 9/23
Arrive Kennebunk ME 923 leaving 9/25
Arrive Yarmouth MA 9/25 leaving 9/29
Arrive Boston 9/29 leave (fly) 10/3

Based on your feedback I'm currently looking at turning our rental car in Saint Andrews NB, taking a bus to Bar Harbor and picking up a new rental car there and turn it back in when we arrive in Boston.....unless you have other ideas!

it is so close!! One country.

Halifax is in West Yorkshire and Boston is just one county away in Lincolnshire... easy. Just over 100 miles.

Seems fine to me , Since your bookings are firm , the only thing I would add is that it adds a bit more driving than my suggestion , but not enough to be an issue , Come back as your trip takes shape , I'll be happy to add more ideas , as you come down the Maine Coast .

It's just not possible to pick up in Canada and drop of in US.

Correct, as it applies to OP's origin/destination.

However, Seatlle-VancouverBC is possible.
If you are willing to pay, Avis-Budget will do a one way rental

We really appreciate all of the suggestions. There didn't seem to be anyway to get from Saint Andrews to Bar Harbor (in spite of internet search suggesting bus as an option). We've been able to modify our travel plans by dropping Saint Andrews and adding Wolfville and Yarmouth NS.

We'll drop off our Canadian Rental car in Yarmouth NS, take the ferry from Yarmouth to Bar Harbor and pick up a new rental car in Bar Harbor. Not sure we would have figured this out without your collective assistance - so thank you!

Anne & Ken

Glad this worked out ! So, two things to consider ( among many ) Since you will be in Bar Harbor , whatever else you do , try to drive down the Schoodic Penensula to Schoodic Point , it's primeval woodland at its best . Also two places to include on your way down to Kennebunk - 1 ) Rockland , ME , a great town , and if you are an art lover , The Farnsworth Museum has a great collection of works by The Wyeth Family ( N.C. Wyeth , Andrew Wyeth and Jamie Wyeth ) 2 ) Camden , ME absolutely worth a stop . Just to push the art a bit more , if you are unfamiliar with the Wyeths , this video about them is wonderful and will add a great deal to your stay in Maine . As you get closer to Massachusetts , there is a surfeit of great stops before you reach Beantown . The Wyeth video - https://youtu.be/jNuGbKIoUds

I have a line of friends and family dotting the Maine coast up to Mount Desert Island and make the trip once or twice a year. I've always wanted to get further, and into NS. I'm envious of your trip!