Best Online Travel Companies in Massachusetts, United States
The 82 best Online Travel companies in Massachusetts, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Lola.
Ranked: Best Online Travel companies in Massachusetts
| # | Company | App-install YoY | Disclosed funding | Last round | Employees | Founder | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | GotoBus Marketplace for booking bus tickets and ondemand services | +7% | — | 78 mo ago | 20 | Jimmy Chen Founder & President | Cart FunctionalityBootstrapMatomo Analytics+5 | — | — |
| 2 | TripAdvisor Online platform providing travel guidance, reviews, and booking functionalities | +6% | $3M | 309 mo ago | 2,845 2,845 → 5,771 (+103%) | Kimi Liu CEO China | DrupalProton MailApple iCloud Mail+30 | 4 patents Social travel recommendation platforms integrating map UI, social networking, and media creation | — |
| 3 | Zipcar Operator of a network providing on-demand access to shared vehicles | +5% | $61M | 186 mo ago | 401 401 → 423 (+5%) | — | Amazon WebstoreDrupalPHP+43 | 50 patents Digital vehicle sharing platform with fleet management, keyless ignition, and occupancy control. | — |
| 4 | FlightView Real-time flight tracking, airport delay information, and travel planning solutions | +1% | — | — | — | Mike Benjamin CEO | — | 5 patents Real-time aviation data collection, analytics, and targeted passenger advertising systems. | — |
| 5 | flightview Flightview Inc. produces innovative apps for mobile devices to allow users the ability to track upcoming and… | +1% | — | — | 12 | — | Node.jsReactNext.js App Router+27 | 5 patents Aviation data analytics and targeted passenger services for flight operations and airport management | — |
| 6 | Blockskye Blockchain-based solutions for travel & entertainment industry | — | $16M | 11 mo ago | 40 | — | Cart FunctionalitySquarespace CommerceSquarespace+26 | 5 patents Electronic commerce transaction processing platforms and methods | — |
| 7 | Guidesly Offers outdoor activities booking solutions | — | $14M | 17 mo ago | 34 | David Lord Founder & CEO | SentryFirebaseGoogle Maps+27 | — | 1 launch · 1 partnership |
| 8 | Groupize Online platform for booking business travel | — | $12M | 28 mo ago | 26 | — | — | — | 1 job opening · 1 launch · 1 partnership |
| 9 | Lola App-based booking platform for business travelers | — | $72M | 87 mo ago | 28 | — | Framer SitesReactcore-js+10 | — | — |
| 10 | FlightCar Watch high-speed online soccer on K+ Full HD - Xoilac TV | — | $47M | 128 mo ago | 79 | — | — | — | — |
| 11 | Tailbox Platform offering stories tied to specific locations | — | $2M | 33 mo ago | 5 | Bayazid Malikov Co-Founder | — | — | — |
| 12 | SmarterTravel Online platform publishing content focusing on travel | — | $10M | 57 mo ago | 45 | Daniel Sau Founder & CEO | Node.jsAmazon Web ServicesAstro+25 | — | — |
| 13 | Floqsta App-based social community platform for travelers | — | $737K | 32 mo ago | — | Michael Huynh Technology Co-founder | — | — | — |
| 14 | Freebird Online platform for flight re-booking in case of delays | — | $16M | 91 mo ago | 27 | — | — | — | — |
| 15 | Wanderu Online bus tickets booking platform | — | $8M | 139 mo ago | 35 | — | Cart FunctionalityFacebook LoginGoogle Sign-in+19 | — | — |
| 16 | Going Online social platform connecting nearby users | — | $8M | 227 mo ago | 63 | — | SentryZendeskNode.js+34 | — | — |
| 17 | Smart Destinations Travel and attractions pass distributors | — | $7M | 192 mo ago | 43 | — | — | 21 patents Location-based marketing and e‑commerce platforms for attraction ticketing and access | — |
| 18 | TRZMO Provider of AI-based omnichannel solutions for e-commerce businesses | — | $1M | 51 mo ago | 36 | — | — | — | — |
| 19 | Skedaddle Trusted SBOBET agent providing online soccer betting services and alternative links | — | $4M | 117 mo ago | 10 | — | — | — | — |
| 20 | Lumo App-based solution for tracking flight delays | — | $3M | 85 mo ago | 7 | Hamsa Balakrishnan Co-Founder and Chief Scientist | StripeAtlassian StatuspageAmazon Web Services+3 | 13 patents Precision irrigation control systems for agriculture and automated self-cleaning pet grooming devices | 1 launch |
| 21 | Bookity Group reservations software for tourist places | — | $3M | 135 mo ago | 9 | — | — | — | — |
| 22 | SkyAuction.com Online travel auction marketplace offering deals on flights, hotels, and more | — | $4M | 293 mo ago | 26 | Michael Hering CEO & President | JavaBootstrapApache HTTP Server+10 | — | — |
| 23 | Wandrian Italy travel experts providing seamless planning, booking, and technology solutions | — | $4M | 253 mo ago | — | — | Squarespace CommerceSquarespaceTypeScript+13 | — | — |
| 24 | Tackle Grab Subscription service for Fishing Baits | — | $1M | 149 mo ago | — | Stash Karandanis CEO & Founder | — | — | — |
| 25 | Dashbell Booking and Reservation management SaaS with partner channels integration | — | $1M | 149 mo ago | 7 | Alexander Torrenegra Co Founder & Board of Directors | — | — | — |
| 26 | FlipKey Vacation rentals marketplace connecting travelers with diverse properties worldwide | — | $500K | 222 mo ago | 30 | — | PHPHandlebarsMustache+19 | 3 patents Online guest feedback collection and analysis systems for short‑term rental accommodations | — |
| 27 | Sleepbox Operator of tech-enabled micro-hotels | — | $250K | 86 mo ago | 2 | Peter Chambers Co-Founder & COO | GoDaddy Website BuilderReactLodash+6 | — | — |
| 28 | Linear Air Reinventing private air travel with flexible, convenient charter flights | — | $300K | 197 mo ago | 39 | William Herp Founder & CEO | JavaGoogle MapsZURB Foundation+25 | — | — |
Top 12 Online Travel companies in Massachusetts
#1
Series C · Boston, Massachusetts · founded 2017 · 40 employees$15.8Mraised▾
Blockskye provides blockchain-based solutions for the travel and entertainment industry. Offers inventory booking and transaction management solutions based on Ethereum blockchain. Provides airlines, hotels, resorts, stadiums with blockchain-enabled booking management to efficiently manage inventories.
- Jul 2025Series C$15.8M
- Apr 2019Series A—
#2
Series A · Boston, Massachusetts · founded 2011 · 34 employees$14.1Mraised▾
Provider of travel agency services. It also supports guides by providing innovative solutions to common challenges faced in the outdoor guiding business. Its platform is used for finding and booking fishing adventures.
- Dec 2024Series A$9.5M
- Jan 2022Seed$4M
- Jan 2021Seed—
- Oct 2020Seed$600K
#3
Series A · Boston, Massachusetts · founded 2011 · 26 employees$11.9Mraised▾
Online platform for booking business travel. The platform enables users to book and manage hotel rooms or accommodation, meeting rooms, and flight tickets as well as make event bookings. Features include payment management, schedule or itinerary management, and more. The solution can also be integrated with other expense management and third-party systems including Concur.
- Feb 2024Series A$100K
- Dec 2022Series A$605K
- Mar 2020Series A$500K
- Apr 2019Series A$2.9M
#4
Acquired · Boston, Massachusetts · founded 2015 · 28 employees$71.7Mraised▾
Lola is an app-based booking platform for business travelers. It allows users to plan, book air tickets, accommodation, car rentals & manage their business trips. It also provides business travelers with customer support & concierge service. The app is available on iOS & Android devices.
- Mar 2019Series C$37M
- Jan 2017Series B$15M
- Apr 2016Series A$19.7M
#5
Deadpooled · Boston, Massachusetts · founded 2011 · 79 employees$46.7Mraised▾
Watch high-speed online soccer on K+ Full HD - Xoilac TV, a leading platform for live soccer streaming. It offers free access to high-quality broadcasts of various soccer leagues and tournaments worldwide. The platform provides live scores, soccer news, match schedules, and league standings. It also features expert analysis and commentary. The website has a user-friendly interface and multiple streaming links for each match. Additional services include statistical data, odds comparisons, and a free livescore application. The platform aims to provide soccer fans with a comprehensive and engaging experience. It offers free access, expert commentary, and a wide range of soccer content.
- Oct 2015Series B$20.7M
- Sep 2014Series A$19.9M
- Apr 2013Series A$5.5M
- Mar 2013Seed$125K
#6
Acquired · Boston, Massachusetts · founded 2000 · 401 employees$60.7Mraised▾
Operator of a network providing on-demand access to shared vehicles. The service allows members to reserve vehicles for short periods. Included are standard damage protection, maintenance, and support. The program offers options for both personal and business use.
- Dec 2010Series G$21M
- Nov 2006Series D$25M
- Jan 2005Series C$10M
- Dec 2002Series B$4.7M
#7
Seed · Cambridge, Massachusetts · founded 2022 · 5 employees$1.5Mraised▾
Platform offering stories tied to specific locations. It offers a platform for personalized tours powered by AI, providing experiences for travelers. Its AI-generated content offers virtual tours and exhibitions, for interactivity and engagement.
- Sep 2023Seed$1.5M
#8
Acquired · Boston, Massachusetts · founded 1998 · 45 employees$9.5Mraised▾
Online platform publishing content focusing on travel. The platform provides expert help, travel tips, destination stories, travel deals, schedule plans & more.
- Sep 2021Series B$9.5M
#9
Seed · Boston, Massachusetts · founded 2021$737Kraised▾
App-based social communnity platform for travelers. Users can connect wit compatible travel companions with similar interests using the app. The platform matches users with compatible travel companions using machine learning and artificial intelligence.
- Oct 2023Seed$25K
- Jul 2023Seed$27K
- May 2023Seed$685K
#10
Acquired · Cambridge, Massachusetts · founded 2015 · 27 employees$16.5Mraised▾
Freebird is an online portal that allows users to rebook trip on any airline at no additional cost when the flight is canceled or significantly delayed, primarily catering to corporate travelers & enterprises. Once a customer enters their flight details with Freebird, they receive alerts about any delays in their flights. They can visit Freebird and book another flight without incurring any extra cost.
- Oct 2018Series A$8M
- Apr 2017Series A$5M
- Nov 2015Series A$3.5M
#11
Series A · Boston, Massachusetts · founded 2012 · 35 employees$8.1Mraised▾
Wanderu is an Online-based platform for booking bus tickets. Uses can book tickets by providing details like location, passenger details, and more. It uses advanced routing algorithm searches for various operators on the platform. It offers various features like real-time tracking, compare various operators, etc. The mobile app is available for both Android & iOS devices.
- Nov 2014Series A$5.6M
- Aug 2013Seed$2.5M
#12
Acquired · Boston, Massachusetts · founded 2005 · 63 employees$8.5Mraised▾
Online social platform connecting nearby users. The platform lets users know the locations of friends and events happening in the city. The platform connects the users with the event-goers before, during, and after events.
- Jul 2007Series B$5M
- Jan 2007Series A$3.5M
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Online Travel coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Sweetie watches where the money and the users are piling in. She covers sector wealth and momentum — the install curves and revenue pools that show which corners of the market are quietly on fire.