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Find Travel Insurance Agents Near You in Pittsfield, MA

Browse travel insurance agents serving Pittsfield, Massachusetts. Updated 2026-07-14.

The top-rated travel insurance agent in Pittsfield, Massachusetts is Pearson Wallace Insurance, LLC, rated 4.9 stars across 113 reviews. Other highly rated options include AAA Pittsfield, Greylock Insurance Agency, MountainOne Insurance. This directory lists 19 travel insurance agents serving Pittsfield.

Showing 19 travel insurance agents in Pittsfield, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Pearson Wallace Insurance, LLC222 South St(413) 464-9390
2AAA Pittsfield660 Merrill Rd(413) 445-5635
3Greylock Insurance Agency5 Cheshire Rd Suite 26(413) 443-5943
4MountainOne Insurance111 Silver Lake Blvd(413) 442-9241
5Shire City Insurance446 South St #1(413) 443-9359
6Wheeler & Taylor Insurance402 East St(413) 448-8224
7Berkshire Travel Group1450 East St #6n(413) 443-9188
8Berkshire Insurance Group43 East St(866) 636-0244
9Berkshire Fairfield Insurance Agency, LLC128 South St(413) 443-0077
10Taillefer Insurance446 South St(413) 445-5616
PW
222 South St
Pearson Wallace Insurance, LLC
Travel Insurance Agent · Pittsfield, MA

Pearson Wallace Insurance, LLC offers a full range of travel insurance services for clients in Pittsfield, MA, including trip cancellation, medical evacuation, and baggage protection policies. It also provides ongoing policy reviews and plan adjustments to meet changing travel needs. Clients receive assistance with claims filing and coverage questions throughout the duration of their trips. The agency serves travelers covering single-family homes, apartments, local retail shops, and area restaurants.

AP
660 Merrill Rd
AAA Pittsfield
Travel Insurance Agent · Pittsfield, MA

AAA Pittsfield serves Pittsfield, MA, and the surrounding Berkshire County area as a dedicated travel insurance agent. The company helps clients evaluate and select coverage for trip cancellations, medical emergencies abroad, and lost luggage. Travelers can receive guidance on comparing policy options to match their specific trip itineraries and personal health needs. The agency also assists with processing claims for delayed departures and emergency medical evacuation services.

GI
5 Cheshire Rd Suite 26
Greylock Insurance Agency
Travel Insurance Agent · Pittsfield, MA

Greylock Insurance Agency provides residential travel insurance services in Pittsfield, MA, helping local clients protect their trips against common disruptions. The agency also offers commercial travel coverage for area businesses and organizations whose employees travel frequently. Service extends to clients throughout Berkshire County and neighboring communities. The agency emphasizes thorough policy explanations and personalized assistance, ensuring customers understand their coverage before departure. Follow-up support is readily available between regular visits, allowing for easy policy adjustments or claims assistance as return travel plans develop.

MI
111 Silver Lake Blvd
MountainOne Insurance
Travel Insurance Agent · Pittsfield, MA

MountainOne Insurance, based in Pittsfield, MA, is known for providing travel insurance agent services for local residents planning domestic or international trips. The agency helps clients compare policies that cover trip cancellation, baggage loss, and emergency medical expenses while traveling. It assists with selecting appropriate coverage limits based on destination and trip duration. A specialty service it can add on is optional coverage for pre-existing medical conditions to ensure comprehensive protection before departure.

SC
446 South St #1
Shire City Insurance
Travel Insurance Agent · Pittsfield, MA

Shire City Insurance in Pittsfield, MA serves travelers by distinguishing between single-trip policies for a specific journey and annual multi-trip plans for frequent travelers needing ongoing protection. Coverage typically includes trip cancellation, interruption, medical expenses, baggage loss, and emergency evacuation assistance. As a local travel insurance agent, the company helps clients compare these options to fit their itineraries and budgets. Services are available on an as-needed basis, with clients contacting them to arrange coverage before each vacation or to set up a recurring annual plan.

WT
402 East St
Wheeler & Taylor Insurance
Travel Insurance Agent · Pittsfield, MA

Wheeler & Taylor Insurance specializes in arranging travel insurance policies for clients in Pittsfield, MA, offering coverage for trip cancellation, medical emergencies abroad, and lost baggage. It also assists local travelers with general insurance needs, including policy reviews and claims guidance. Whether planning a winter ski trip to the Berkshires or a summer vacation overseas, the agency helps residents address unexpected disruptions that can occur before or during their journey.

BT
1450 East St #6n
Berkshire Travel Group
Travel Insurance Agent · Pittsfield, MA

Berkshire Travel Group provides travel insurance policies for individuals and groups, specializing in add-ons such as trip cancellation, medical evacuation, and baggage protection for travelers departing from Pittsfield, MA. Its plans cover domestic and international itineraries, offering coverage for common travel disruptions including delays and lost documents. The agency serves commercial sectors ranging from corporate offices to warehouses and food service operations.

BI
43 East St
Berkshire Insurance Group
Travel Insurance Agent · Pittsfield, MA

For travelers from Pittsfield planning a winter ski trip or a summer excursion to the Berkshires, a solid travel insurance plan can provide needed security against trip cancellations or medical emergencies abroad. Berkshire Insurance Group works with clients to review available policy options without pushing a single solution. Their approach begins with an open conversation about the traveler’s itinerary and health needs. This initial assessment helps determine the appropriate level of coverage before committing to any specific plan.

BF
128 South St
Berkshire Fairfield Insurance Agency, LLC
Travel Insurance Agent · Pittsfield, MA

Berkshire Fairfield Insurance Agency, LLC serves travelers from Pittsfield, Massachusetts, handling trip protection needs for vacationers and business travelers alike. Its advisors explain common travel insurance coverages, such as trip cancellation, medical evacuation, and baggage delay. Clients rely on clear policy comparisons tailored to individual itineraries. The agency also assists frequent fliers with annual multi-trip plans. Coverage extends to residents throughout Berkshire County, including clients in the neighboring community of Lenox.

TI
446 South St
Taillefer Insurance
Travel Insurance Agent · Pittsfield, MA

Serving Pittsfield, Massachusetts, and the surrounding Berkshire County communities, Taillefer Insurance provides travel insurance for local residents planning domestic or international trips. The agency handles policies covering trip cancellations, medical emergencies abroad, and lost baggage protection to ensure traveler peace of mind. This agency reviews each client’s itinerary, health needs, and travel risks to recommend a suitable coverage plan for their specific journey.

GI
150 West St
Greylock Insurance Agency
Travel Insurance Agent · Pittsfield, MA
(413) 236-4840
greylockinsurance.com
MI
101 South St
MountainOne Insurance
Travel Insurance Agent · Pittsfield, MA
(413) 445-5648
mountainone.com/insurance
SF
128 South St
Scarafoni Financial Group LLC
Travel Insurance Agent · Pittsfield, MA
(413) 443-5300
scarafonifinancial.com
MJ
55 North St #304
Mclaughlin John
Travel Insurance Agent · Pittsfield, MA
(413) 499-0620
johnfmclaughliniii.nm.com
NM
55 North St #304
Northwestern Mutual
Travel Insurance Agent · Pittsfield, MA
(413) 499-0620
northwesternmutual.com/financial-professionals
BI
75 South Church Street Pittsfield Lenox
Berkshire Insurance Group
Travel Insurance Agent · Pittsfield, MA
(866) 636-0244
HN
75 S Church St
Health New England-Berkshire
Travel Insurance Agent · Pittsfield, MA
(413) 499-8887
RT
43 Adam St
R&S traveler's
Travel Insurance Agent · Pittsfield, MA
(413) 281-8137
rstravelers.inteletravel.com/booktravel.cfm
AA
First St
Anywhere Anyway Travel
Travel Insurance Agent · Pittsfield, MA
(413) 553-7710
evotravelagent.com/anywhere_anyway_travel

What Does a a Travel Insurance Agent in Pittsfield Cost?

Typical travel insurance costs in Massachusetts range from 4 percent to 10 percent of your total trip cost. For a 1000 dollar trip you might pay 40 to 100 dollars for a standard policy. Premiums vary based on your age trip length destination and coverage limits. This is general information and not insurance advice.

About travel insurance agents in Pittsfield

Travel insurance agents in Pittsfield Massachusetts help residents and visitors find coverage for domestic and international trips. Massachusetts state law requires agents to hold a valid insurance producer license. Agents can explain policy terms and help you compare plans from multiple carriers.

Frequently Asked Questions

What does a travel insurance agent in Pittsfield do?

A travel insurance agent helps you review and purchase travel insurance policies. They explain coverage options like trip cancellation medical evacuation and baggage loss. Agents in Pittsfield can also help you file claims with the insurance company.

Do I need travel insurance for a trip from Pittsfield?

Travel insurance is not required by Massachusetts law but is recommended for many trips. It can cover unexpected medical costs trip cancellations and lost luggage. Some tour operators and cruise lines may require you to have a policy.

How do I choose a travel insurance agent in Pittsfield?

Look for a licensed agent who specializes in travel insurance. Ask about their experience with different policy types and insurers. You can verify an agents license through the Massachusetts Division of Insurance website.

Travel Insurance Agents in Other Massachusetts Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each travel insurance agent's credentials and current standing with your state Department of Insurance.